10 Superb Spring Breaks For Families in the Midwest

This page may contain affiliate links to third-party tour operators and booking platforms. Should you make a qualifying booking after using our affiliate link, we make a commission.

1. Hocking Hills, Ohio

Nestled in southeastern Ohio, Hocking Hills State Park transforms into a wonderland of cascading waterfalls and emerging wildflowers during spring. The moderate temperatures (averaging 60°F/15°C) create perfect conditions for exploring the park’s network of trails winding through dramatic sandstone cliffs and mysterious caves.

Spring rainfall enhances the waterfalls, making them particularly spectacular at Cedar Falls and Ash Cave. Families can enjoy guided nature walks to spot returning migrating birds and early-blooming wildflowers like spring beauties and trilliums.

The region’s unique microclimate means waterfalls might still feature fascinating ice formations while spring flowers bloom nearby. Local cabin rentals offer lower shoulder-season rates, and popular hiking trails are significantly less crowded than during peak summer months.

2. Door County, Wisconsin’s Cherry Coast

This picturesque peninsula comes alive in spring as millions of cherry and apple trees burst into bloom, creating a spectacular display of pink and white blossoms. The moderate spring temperatures (mid-50s°F/12-13°C) are perfect for exploring the five state parks, each offering unique perspectives on Lake Michigan and Green Bay.

Spring brings excellent conditions for lighthouse tours, gallery hopping in charming villages like Fish Creek and Ephraim, and watching migrating birds at Newport State Park. Families can enjoy off-season rates at lakeside resorts, and the smaller crowds mean easier access to popular activities like fish boils and cherry pie tastings.

The spring season also offers unique opportunities for foraging morel mushrooms and watching the return of the peninsula’s famous wildlife.

3. The Shawnee Hills Wine Trail, Illinois

This hidden gem in southern Illinois sits along the Shawnee National Forest and offers an unexpected spring adventure. The area warms earlier than northern regions, with comfortable temperatures around 65°F/18°C by spring break. Families can explore the unique Giant City State Park, where massive sandstone formations create natural playgrounds.

Spring highlights include the blooming of over 20 species of wild orchids and the emergence of unique rock formations as winter foliage clears. The nearby Shawnee Hills Wine Trail offers family-friendly vineyards with stunning views of awakening vineyards, while parents can enjoy wine tastings.

Kids will love spotting returning bald eagles and exploring the ancient rock formations. Local bed-and-breakfasts offer seasonal specials, and the spring timing means you’ll avoid the summer humidity while still enjoying outdoor activities.

4. Mammoth Cave National Park, Kentucky

While technically on the southern edge of the Midwest, this UNESCO World Heritage site offers perfect spring break timing. The cave’s constant 54°F/12°C temperature makes underground exploration comfortable year-round, while spring surface temperatures (mid-60s°F/18°C) are ideal for exploring the park’s extensive trail system.

Spring break visitors benefit from smaller tour groups in the world’s longest cave system, which allows for more intimate experiences and better photo opportunities. Above ground, the Green River Valley explodes with dogwood and redbud blooms, while returning warblers fill the forest with song.

Families can combine cave tours with river activities, as spring rainfall creates excellent paddling conditions. The park’s campgrounds and nearby accommodations offer better availability and rates compared to peak summer season, and spring visitors avoid the intense humidity of Kentucky summers.

5. Taylors Falls, Minnesota

Straddling the St. Croix River on the Minnesota-Wisconsin border, Taylors Falls offers a unique spring adventure as the river awakens from winter. Interstate State Park, split between both states, features dramatic glacial potholes and cliffs that are particularly striking in spring when the melting snow increases river flow.

Spring temperatures (mid-50s°F/13°C) are perfect for hiking the rocky bluffs and exploring the glacial formations.

Families can watch early-season kayakers navigate the rapids or take the season’s first scenic boat tours on the river. The area’s microclimate supports unique plant life, including early-blooming cliff plants and rare ferns.

Local outfitters offer special spring rates on equipment rentals, and the historic downtown area is less crowded, allowing families to explore the unique shops and restaurants at a leisurely pace.

6. Broken Kettle Grasslands Preserve, Iowa

As Iowa’s largest remaining prairie, this hidden gem comes alive in early spring with the return of migrating birds and the first prairie flowers. The preserve is home to a genetically pure herd of bison, which are particularly active in spring as new calves arrive. Spring temperatures (around 60°F/15°C) create ideal conditions for hiking the preserve’s trail system and photography opportunities.

The Loess Hills setting offers spectacular views across the Missouri River Valley, and spring’s clear air makes for excellent visibility. Families can participate in guided prairie walks to learn about the unique ecosystem and its spring awakening. The nearby city of Sioux City provides comfortable accommodations, and spring visitors often have the preserve almost to themselves, offering an intimate experience with Iowa’s natural heritage.

7. Ha Ha Tonka State Park, Missouri

This extraordinary park in the Lake of the Ozarks region offers a fascinating blend of natural and historical attractions that shine in spring. The ruins of a 1905 castle overlook a landscape bursting with dogwood and redbud blooms, while spring temperatures (mid-60s°F/18°C) create perfect conditions for exploring the park’s extensive cave system and natural bridge.

The park’s unique karst geology features numerous springs and sinkholes that are particularly active after winter thaws. Families can explore more than 15 miles of trails, including boardwalks that showcase the park’s varied ecosystems.

Spring break timing means fewer crowds at popular spots like the castle ruins and natural bridge, while the park’s wide variety of wildflowers begins their annual show. Local resorts offer shoulder-season rates, and the nearby Lake of the Ozarks provides additional recreational opportunities without the summer crowds.

8. Sleeping Bear Dunes National Lakeshore, Michigan

While famous as a summer destination, this stunning Lake Michigan shoreline offers a special magic during spring break. The massive dunes and coastal bluffs provide dramatic views of the awakening landscape, and spring temperatures (mid-50s°F/12-13°C) make dune climbing more comfortable than in summer heat.

Early spring visitors might catch the tail end of winter’s ice formations along the shore while witnessing the return of migratory birds. The Pierce Stocking Scenic Drive typically opens in spring, offering accessible views of the dunes and lake. Families can explore the historic Port Oneida Rural Historic District or search for Petoskey stones along the beach without summer crowds.

The nearby towns of Glen Arbor and Empire offer cozy accommodations at reduced spring rates, and local maple syrup producers welcome visitors during the spring tapping season. The combination of fewer visitors and awakening nature creates a unique opportunity to experience this national treasure intimately.

9. Starved Rock State Park, Illinois

This spectacular park along the Illinois River offers one of the Midwest’s most dramatic spring awakenings. The park’s 18 canyons come alive with seasonal waterfalls as winter ice melts, creating an other-worldly landscape. Spring temperatures (mid-50s°F/12-13°C) are ideal for exploring the 13 miles of well-marked trails that wind through towering bluffs and scenic canyons.

Wildflower enthusiasts will discover over 200 species beginning their annual show, while bird watchers can spot returning bald eagles and migrating waterfowl. The historic Starved Rock Lodge offers comfortable accommodation with spring specials, and guided hiking tours help families safely explore the park’s hidden waterfalls and scenic overlooks.

Spring break timing means the spectacular ice falls are often still visible while early wildflowers begin blooming, creating a unique seasonal overlap that summer visitors miss entirely.

10. The Bridges of Madison County, Iowa

This iconic region takes on a special charm in spring when the famous covered bridges emerge from winter against a backdrop of blooming dogwoods and redbuds. Spring temperatures (around 60°F/16°C) create perfect conditions for the scenic driving tour connecting all six remaining historic covered bridges.

Families can enjoy photography workshops focused on capturing the bridges in spring light, and the quiet country roads are ideal for cycling adventures. The town of Winterset offers charming B&Bs with spring specials, and the John Wayne Birthplace Museum provides indoor entertainment if spring showers appear.

Local maple syrup producers welcome visitors during the spring tapping season, and families can enjoy demonstrations at nearby traditional farms as they begin their spring activities. The spring timing means fewer tourists at popular photo spots, and the clear spring air makes for spectacular sunset photos of the bridges.

© Family Road Trip 2026

The post Hidden Gems: Discovering the Magic of Midwest Spring Break appeared first on Family Road Trip.

1. Iowa Scenic Drives: Loess Hills National Scenic Byway

• Distance: 220 miles 
• Time Needed: 5 hours to 1 day 

The landscape of Loess Hills is comprised of prairies, bluffs, and rolling hills, making it one of the most scenic places to drive in Iowa. 

Along the way, there are lots of historic sites and parks to visit. You can check out places like the Historic General Dodge House, the impressive mansion of a former Civil War general. 

Lewis and Clark Monument is another great place to include on this byway in Iowa. This overlook has an impressive view toward the west and marks one of the stopping points of Lewis and Clark, the famous travelers who charted the territory west of the Mississippi. Not only is the overlook a good place to stop for photographs, but there’s also a picnic area where you can enjoy a lunch break on this Iowa drive. 

In addition to the 220 miles of the official route, there are 185 miles of excursion loops to appreciate the Iowa scenery. Many of these are gravel routes that offer a way to explore some of the wilderness and feel like you’re really escaping civilization for a while. 

2. Iowa Scenic Drives: Western Skies Scenic Byway

• Distance: 142 miles 
• Time Needed: 3-6 hours

If you’re already planning on traveling Interstate 80, then the Western Skies Scenic Byway is a great drive in Iowa to take. This route may be a bit longer than the direct 1-80 route, but the peaceful scenery makes it well worth the time. 

This Iowa scenic drive gets its name from the prairie landscape and open skies. There are also a number of historic locations along the route, including the Harrison County Historical Village, where the drive begins. 

Elk Horn and Kimballtown are also great places to stop, both of which began as early Danish settlements and still preserve a lot of their historic charm. Check out some of the local artisan shops in these towns, or pick up a treat at one of the bakeries. 

Outdoor enthusiasts will like the variety of activities that can be added to this scenic drive in Iowa. Whiterock Conservancy is a great place to go hiking or even spend a few nights camping in the region known for having the darkest sky and the best star-gazing opportunities in Iowa. 

3. Iowa Scenic Drives: Covered Bridges Scenic Byway

• Distance: 82 miles
• Time Needed: 2-4 hours 

You might guess by the name of this Iowa byway that what makes this particular route unique are the numerous covered bridges along the way. The movie and musical The Bridges of Madison County was actually filmed here, something which some of the towns still take pride in. 

Make sure you stop in Winterset, a town near the center of Madison County, which is known for its historic limestone courthouse and has received a National Historic District designation. There are also plenty of local shops and fun restaurants around the town square. 

You’ll already have lots of opportunities to see the peaceful landscape along this scenic drive in Iowa, but if you’re interested in a more immersive nature experience, you’ll want to stop at the Madison County Historic Complex. 

Add an afternoon of kayaking to your trip, or check out some of the hiking trails to stretch your legs. You’ll also get great views of the North River and Middle River Valleys. 

When to go: Spring through fall has the best views, especially if you want to walk around and explore. 

4. Iowa Scenic Drives: River Bluffs Scenic Byway

• Distance: 109 miles
• Time Needed: 2 hours to 1 day (or more)

It won’t take much to convince you that this is one of the best scenic byways in Iowa, thanks to the incredible landscape formed by three rivers: Turkey, the Volga, and the Mississippi. 

From your vehicle, you’ll get stunning views of the bluffs for which the route gets its name, as well as peaceful forests and rolling hills. Thirteen small towns dot the route, many of which have a unique historical atmosphere. Thanks to the quaint shops and friendly vibe, this area is sometimes called Iowa’s “Little Switzerland.”

No road trip in Iowa would be complete without adding on at least a few outdoor activities, and you’ll find plenty of options on this route. There are parks with hiking trails, unique caves formed by the erosion of the rivers, and water access points for fishing and kayaking. 

When to go: Summer is best for outdoor activities, but spring and fall are also excellent for views of the flowers and autumn colors. 

5. Iowa Scenic Drives: Driftless Area Scenic Byway

• Distance: 144 miles 
• Time Needed: 3 hours to 1 day 

Sometimes considered the most scenic drive in Iowa, you’ll understand how this route got its name once you start to pass through the untouched natural beauty of limestone bluffs and rivers meandering through forests. In the midst of the peaceful nature, relax and let yourself drift away through Iowa’s scenery!  

Not only is this Iowa drive stunning, but it also holds endless opportunities for outdoor recreation, like hiking in the state parks or fishing and boating on the Mississippi, Yellow, or Upper Iowa Rivers. 

Along with the natural beauty, you’ll also encounter interesting historic landmarks like stone churches and bridges which date back to the time of the pioneers who first settled in the area. Stop for lunch at a local diner at one of the little towns along the way, or pick up a souvenir at a small boutique. 

When to go: This is one of the best drives in Iowa in the fall since the entire route is covered with colorful deciduous trees. Spring and summer are also good for outdoor scenery and activities. 

6. Scenic Drives in Iowa: Iowa Valley Scenic Byway

• Distance: 77 miles 
• Time needed: 2-5 hours 

The Iowa Valley Scenic Byway offers a great combination of history and natural beauty. On the western end of the route, you’ll find the Meskwaki Settlement, which is the state’s only official resident Native American community. Visit the Meskwaki Cultural Center & Museum to learn about the history and significance of the region as well as view stunning artifacts of beadwork and weaving. 

You’ll find no shortage of quirky and unique stops on your Iowa road trip along this route. Check out Traer’s Salt and Pepper Shaker Gallery or Gladbrook’s Matchstick Marvels Museum for something you won’t get to see on other drives! 

In addition to the small-town charms, there are also plenty of places to get out and explore the landscape around the Iowa River Valley. Favorite activities include fishing, hiking, and bird watching. 

You’ll already get plenty of lookouts over the bluffs, but if you want an even better perspective of the Iowa scenery, you can make a pit stop close to Chelsea, where there’s a lookout platform built in the shape of an eagle which is a perfect place for photographs. 

If you’re driving this scenic route in Iowa during July, then a stop at Lily Lake in Amana is a must. Each year in summer, this lake is known for the thousands of water lilies that cover the surface in a beautiful array of gold and white! 

More Inspiration And Tips Road Tripping In The Midwest

Always check weather conditions before you set out, especially in winter; visit www.511ia.org for the latest information from the Iowa Department of Transport.

Looking for more inspiration beyond Iowa? Check out our round-up of the best scenic drives in the Midwest; plus, we’ve got detailed guides to hitting the roads in Wisconsin, Illinois, Minnesota, and many more in our scenic driving guides to the United States!
Never forget a road-tripping essential again! Get your family and your vehicle organized before hitting the road with our road trip checklist (with a printable PDF checklist you can tick off as you go!)

© Family Road Trip 2026

The post 6 Sensationally Scenic Drives in Iowa appeared first on Family Road Trip.

Best stops between the Windy City and Yellowstone National Park

Yellowstone National Park is one of the most popular road trip destinations in the United States; people drive to Yellowstone from all corners of the country and for good reason! The incredible geysers, huge canyons, and abundance of wildlife make it a place unlike any other. 

Driving from Chicago to Yellowstone may be a big endeavor, but it’s also a trip that’s full of opportunities to explore along the way. Making your way west across the United States, a Chicago to Yellowstone drive uses some of the same routes as the pioneers who first traveled in covered wagons. 

Read ahead on this guide to the ultimate Chicago to Yellowstone road trip so you can learn about the fascinating historic landmarks, huge cultural cities, and incredible natural wonders along the way. 

Distance from Chicago to Yellowstone National Park 

The most direct route from Chicago to Yellowstone covers roughly 1,390 miles. This drive takes you on I-80 West from Chicago to Omaha. From Omaha, you cross over to Sioux Falls, then follow 1-90 west to Buffalo, Wyoming. From here, you continue on state roads to reach the East Entrance of Yellowstone.  

How Long Do I Need to Drive from Chicago to Yellowstone?

If you were to drive to Yellowstone from Chicago without stopping, it would take about 20 hours, depending on traffic and weather conditions. 

To make the most of your Yellowstone National Park road trip, we’d highly recommend planning for a minimum of four days for this scenic route. If you have time, it’s not a bad idea to plan for a week or two to complete the drive so you can stop at more parks and cities along the way! 

Best Time of Year to Drive from Chicago to Yellowstone

Summer is by far the most popular time of year to drive to Yellowstone, thanks to the great opportunities for hiking, swimming, rafting, and other attractions around the park. However, summer is also the season when you’ll need to contend with the most tourists, and temperatures can sometimes become very hot. 

The “shoulder seasons” of spring and fall are good picks since the weather is typically mild, and there aren’t quite so many tourists. 

Although it’s possible to drive Chicago to Yellowstone National Park in winter, keep in mind that many of the accommodations in the park are closed in this season and driving conditions can be tricky. However, if you’re a skier or winter enthusiast, this may suit you just fine! 

Best Stops On A Chicago To Yellowstone Road Trip

Now that you have an idea of what the logistics of a drive from Chicago to Yellowstone entail, here are some of the top places to stop along the way.  

Catch these scenic drives in Illinois before you set off cross-country!

Des Moines, Iowa

Driving from Chicago to Des Moines takes between 5 and 6 hours, depending on how many stops you make, so Des Moines is one of the best places to take a leisurely lunch break for early starters or spend your first night on your road trip to Yellowstone. 

You’ll find a variety of cool art exhibits at the Des Moines Art Center, which has an impressive collection from artists, including Georgia O’Keefe and Henri Matisse. 

Des Moines is also considered to have one of the best farmers’ markets in the country. Farming is a big part of the economy and lifestyle of Iowa, and picking up some fresh snacks or local crafts is a great addition to your Chicago to Yellowstone road trip! 

Sioux Falls, South Dakota

The largest city in South Dakota is a great place to spend the night as you drive to Yellowstone. With a great combination of history, natural beauty, and culture, you could spend just an overnight to rest up or spend a few days exploring. 

Even if you don’t have much time, you can stop to visit Falls Park in the center of the city, where you can view the impressive waterfalls the city is named after. Wander along the paths or rent a bike if you want to venture further on the 35 miles of bike trail crisscrossing the city. 

To experience some of the cultures of the city, the Orpheum Theatre is the place to go. Since 1913 this theatre has been the hub of the city’s jazz and blues scene and performing arts events. Check out what music or theater events are on your time in the city for a special treat! 

If you have a little more time in Sioux Falls, you can visit the nearby Palisades State Park, about 30 minutes outside the city. The impressive cliffs, winding rivers, and stunning quartz formations of this park make it a top hiking and swimming location in the state. 

Badlands National Park, South Dakota

The other-worldly landscape of the Badlands is a must-visit spot on a road trip to Yellowstone. At the very minimum, you should stop to take some photographs from one of the lookout points along the drive, but it also shouldn’t be out of the question to spend a night or two! 

Covering over 250,000 acres, the Badlands holds stunning opportunities for hiking. Window Trail is a good option for an easy path that’s kid-friendly and doesn’t take too long (but still holds plenty of jaw-dropping views!). Experienced hikers can check out the Cliff Shelf, which, as the name suggests, cuts close to red-rock cliff drops. 

In addition to the geological formations, the park is also known for its wildlife, including bison and antelope. Throughout spring and early summer, you’ll be treated to a beautiful array of prairie wildflowers interspersed with tall grasses. 

Badlands has an excellent campground if you want to spend a night under the stunning starry sky of South Dakota or there is Cedar Pass Lodge (seasonal, April to October) within the park. Keep in mind that reservations can fill up quickly, so make sure to book in advance! 

The other alternative is to continue onward to Rapid City, just 75 miles further west and make this your based for a couple of days exploring in South Dakota.

Rapid City, South Dakota

Rapid City is the gateway to the Black Hills National Forest and a prime home base for exploring some of the nearby attractions like Mount Rushmore. 

In the downtown area of Rapid City, there’s a great array of local boutiques and restaurants as well as plenty of accommodation options, so you can spend a day or two here as you drive from Chicago to Yellowstone National Park. 

Check out the City of Presidents exhibit, which features bronze replicas of former American presidents around the downtown area. These statues make perfect spots for photographs of your trip and are a fun way to teach young kids about U.S. history! 

Nearby, there are lots of options for hiking or other fun outdoor activities like horseback riding tours and rafting down rivers. 

Mount Rushmore National Memorial, South Dakota

The best road trip to Yellowstone across South Dakota must include a visit to Mount Rushmore. One of the most famous national landmarks of the United States, this huge 60-foot-tall carving features the faces of four of the most influential presidents in U.S. history: George Washington, Theodore Roosevelt, Thomas Jefferson, and Abraham Lincoln. 

There are a few places to appreciate the carving, and the best might be Grand View Terrace, where you’ll get the classic perspective of the monument. Plus, there are also telescopes here for use in case you want to get an even closer look at the artisanship of the carving! 

If you have more time than a stop at Grand View Terrace, you can include a walk along the Presidential Trail. This half-mile trail is easy and paved, making it good for families with young kids, and it will bring you closer to the base of the mountain. 

Mount Rushmore is a spot you’ll definitely want to have photos of to commemorate your Chicago to Yellowstone road trip! 

Crazy Horse Memorial, South Dakota

Another of the landmarks close to Rapid City you won’t want to pass up is Crazy Horse Memorial. About 16 miles away from Mount Rushmore, it’s easy to visit both of these landmarks in one day during a drive to Yellowstone. 

This memorial is still in progress and is being built to commemorate the Lakota Sioux warrior Crazy Horse. Once it’s completed, it will be the largest monument in the world!

From US Highway 16/385, you can pull off into the memorial’s entrance, and from here, there’s a shuttle bus that will take you right to the mountain’s base for an up-close view of the impressive construction in the making. 

You can also check out the visitor center with fascinating history on Mount Rushmore and the Crazy Horse Memorial, as well as pictures of the progress through the years. 

Wind Cave National Park, South Dakota

Wind Cave National Park is a wonder to behold both above and below ground. Some people even say that opportunities for spotting wildlife which make their home in the mixed-grass prairie of this park rival Yellowstone! 

On any trip to Yellowstone, you’re guaranteed to see animals like bison and elk, but Wind Cave has a few other surprises which Yellowstone lacks. 

As you may have guessed from the name, the caves of this national park are what set it apart from other sites in the U.S. Keep in mind that to enter the caves, you have to be part of a guided tour. There are a couple of options for tours, most of which last about an hour and are fairly easy. If you’re interested in a more difficult cave excursion, there are longer tours that take you deeper into some of the lesser visited areas of the caves.  

Make sure you book any cave tours well in advance since they fill up very quickly, especially in the peak tourist season of summer! 

Devil’s Tower, Mount Rushmore, Crazy Horse, and Wind Cave National Park are all within driving distance from Rapid City on a day trip, ortry the smaller town of Custer, well located to these key attractions in South Dakota.

Devils Tower National Monument, Wyoming

If you have time to add an extra loop to your Chicago to Yellowstone National Park road trip, we’d highly recommend stopping at Devils Tower.

This natural formation is sacred to the Native American tribes who inhabited the Dakotas before the formation of the United States, and it remains a protected site that is capable of inspiring wonder in every visitor. 

The tower was formed from ancient volcanic activity and rose a stunning 867 feet from the flat plains surrounding it. Unfortunately, there’s no way to get to the top of Devil’s Tower unless you’re a seasoned rock climber with a climbing permit, but the view from the base is more than impressive enough to warrant a visit. 

There are a number of hiking trails around Devil’s Monument, the most popular of which is the short 1.3-mile-long Devil’s Tower Trail which is paved and forms a loop around the tower. If you’re looking for a hike without as m

It is a long drive from here to the next few highlights in the north of Wyoming, so be prepared to fuel up and spend a full day on the road.

Shoshone National Forest, Wyoming

If you’re interested in experiencing the stunning landscape of the wild west without the crowds, which are guaranteed to be part of any trip to Yellowstone, then we’d highly recommend planning to stop at the Shoshone National Forest.

You could make it a short afternoon excursion to check out one of the hiking trails, or it would be easy to spend an entire week or more in this wilderness wonderland! 

Covering about 2.4 million acres, Shoshone National Forest is full of pristine mountain lakes, the crossroads of three mountain ranges, and the same sort of variety of wildlife you’ll find at Yellowstone. 

There are a variety of campsites around Shoshone, some of which are first-come-first-serve and others that require reservations. Amenities at campsites also vary, some with running water and toilets, and others with only latrines. Shoshone also has a few limited cabin options, but there are no lodges or hotels here like there are in and around Yellowstone. 

Hiking is one of the most popular attractions of Shoshone. There are easy to moderate trails like Popo Agie Falls Trail, which leads to a beautiful cascading waterfall and swimming hole. More experienced hikers may want to check out the Stough Creek Basin Trail which is a seven-to-eight-hour hike with spectacular mountain views and overlooks over a rushing mountain river.

Grand Teton National Park, Wyoming

A neighboring national park of Yellowstone, Grand Teton is a little bit out of the way for a road trip from Chicago to Yellowstone, but it’s still very manageable to include in your wild west adventure, before or after your Yellowstone visit. 

The park gets its name from its tallest mountain peak, Grand Teton, which towers 13,700 feet! Other smaller (but still impressive) mountains cover the park along with grasslands, forests, rivers, and alpine lakes. 

Take a boat ride out onto Jenny Lake or hike to one of the numerous waterfalls which are found all around the park, like the famous Hidden Falls. 

The Snake River winds its way through the park, and during the summer, it’s a popular spot for kayaking, swimming, river rafting, and jet boating. Other park activities include horseback riding tours, rock climbing, camping, fishing, and skiing in the winter – Jackson Hole being one of the most popular ski resorts in Wyoming.

Yellowstone East Entrance, Wyoming

A drive from Chicago to Yellowstone National Park will take you to the East Entrance. This entrance is the gateway to Yellowstone Lake, which sits at an elevation of 7,733 feet and is an impressive 20 miles long. 

The East Entrance of Yellowstone is generally the less busy entrance to the park, but it’s also farther from some of the top attractions like Old Faithful and Yellowstone Canyon.

We’d recommend spending a few nights on the east side of the park to see the lake and some of the smaller geysers, then loop around to the North or West Entrance of Yellowstone to visit some of the other wonders of Yellowstone. 

Lodge bookings within the national park fill up fast over the summer months, as do popular Yellowstone camping spots. Alternatively, close the East Entrance you’ll find accommodation options in Wapiti. If you are driving through the park, close to the West Entrance you’ll find several more motel inn, hotel and lodge options in West Yellowstone.

More Tips On Your Road Trip Chicago to Yellowstone National Park

Be aware of crossing time zones on this trip; Illinois, Iowa and South Dakota are in CST/CDT, crossing to Wyoming and Montana, you are in MST/MDT – a one hour time difference.

Pack a variety of clothes; even in the summer, temperatures can drop during the night, so it’s a good idea to have layers. 

Keep in mind that on a drive from Chicago to Yellowstone, there will be several long stretches of road without good stopping points. Check a map to plan for stops to get gas, pick up snacks, or take a rest break – we recommend Road Trippers for this 

Seeing wildlife is one of the best parts of a trip to Yellowstone, but always remember to keep your distance and never try to feed wild animals! 
For latest road conditions on your journey, you may want the Wyoming 511 app, South Dakota 511 or Iowa 511 handy

Further Guide For Road Tripping to Yellowstone

There are many different ways you can approach a road trip to Yellowstone; straddled across three states, Wyoming, Montana and Idaho, your nearest major international airports are to the south and west:

Follow this road trip itinerary from Salt Lake City to Yellowstone, taking in the magic of Grand Teton and Idaho Falls on your way

From the west, follow this incredible road trip itinerary from Seattle to Yellowstone, taking you through the highlights of Washington State, Idaho and Montana with several detours and route alternatives that can see you in Glacier National Park and Mt Rainier National Park.
After Yellowstone, why not take the incredibly scenic drive through Montana to Glacier National Park. You could extend this majestic journey even further from Glacier to Banff in Canada or try these Wyoming scenic driving routes.

More Road Trips From Chicago

Check out these 9 easy day trips and short drives from Chicago
You can easily tackle some of these scenic drives in Illinois over a weekend
For another long adventure from Chicago, why not check out our driving itinerary from Chicago to Niagara Falls, or Chicago to New York City

© Family Road Trip 2026

The post Sensational Chicago to Yellowstone Road Trip Itinerary appeared first on Family Road Trip.

From gorgeous state parks to charming towns and bustling cities, there’s nothing quite as nostalgic as driving through the American Midwest.

While most travelers to the USA usually target its bustling cities and gorgeous coasts the Midwest still remains pretty overlooked on most visitors’ radar. Still, this gorgeous region of America is definitely worth exploring, especially for those yearning for an epic road trip filled with excitement, majestic vistas, and spots that give you that back-in-time feeling.

From roads that will have you driving through haunted places in Missouri to chasing waterfalls across Ohio, here are a few of the most epic Midwest road trips that need to be on your radar!

12 Epic Midwest Road Trips

1. Chicago to St. Louis on Route 66

On the lookout for the ultimate Midwest road trip? Look no further than the classic Route 66 from Chicago, Illinois to St. Louis, Missouri, which is also known as “The Mother Road”.

Route 66 actually starts in Chicago and runs all the way to Santa Monica on the West Coast, but if you don’t want to go the entire way, focusing on the Midwest part of the road trip is enough to experience some of the best it has to offer.

Simply put, there is probably no road trip in the entire USA that is as full of classic Americana as the so-called “King of All Roads”. The Midwest portion between Chicago and St. Louis doesn’t slack when it comes to old-fashioned diners, classic service stations, family owned-cafes, cornfields, sleepy towns, and tons of kitschy landmarks.

Start in Chicago, where you can see all the city highlights like the Sears Tower and the Buckingham Fountain before heading to the corner of Michigan Ave. and E. Adams Street, where you’ll find the iconic “Route 66 Starts Here” sign!

Continue onwards to Lyons and check out the Hoffman Tower. Next, head to Joliet and take some time to visit the Joliet Area Historical Museum before hopping back into the car. Along the way, make a stop in the town of Bloomington, where you can stretch your legs by visiting the emblematic Illinois Route 66 Hall of Fame and Museum.

Other unique sights and landmarks you’ll find along the way are the Railsplitter Covered Wagon and the Watermelon Lincoln Monument in Lincoln, the World’s Largest Ketchup Bottle, the Our Lady of the Highway Shrine, the Soulsby Service Station, and so much more!

Once you catch a glimpse of St. Louis Arch, you’ll know the journey is over, but even then, you’ll still find plenty of incredible things to do in St. Louis to make parting a lil’ easier. For a quintessential Midwest experience (and a great excuse to toast the end of this Midwest road trip), don’t miss out on sipping a few beers at the iconic Anheuser-Busch Brewery.

2. St. Louis to Kansas City

Starting in St. Louis and ending in Kansas City, this route will take you through some of the most culture-filled cities and quintessential wild terrain in the southern part of the Midwest.

Start off in St. Louis, where you can spend the day checking out the iconic Gateway Arch over the Mississippi River and a couple of unique museums. From here, head to the Lake of the Ozarks, where you’ll get to bask in some serious lakeside fun with gorgeous views all over.

The city of Columbia is next on the itinerary, where you’ll get to choose from a ton of different activities ranging from outdoor adventures at the nearby Finger Lakes State Park to an afternoon spent checking out local works of art at the Columbia Art League.

Cap off your Kansas road trip touring Kansas City’s numerous memorials and statues. Then, change the mood at the American Jazz Museum and take a stroll through Kansas City’s 18th & Vine Historic Jazz District to finish one of the best Midwest road trips with a bang!

3. Sault Sainte Marie to Leland Michigan Road Trip

Driving from Michigan’s Upper Peninsula to the Lower Peninsula is a jaw-dropping experience and one of the best drives in the Midwest. Starting in Sault Sainte Marie and ending in Leland, it’s hard to beat the majestic wilderness that you’ll get to gawk at the entire way.

Begin in Sault Sainte Marie, a sleepy town perched between Lake Superior and Lake Huron, an ideal lake vacation spot in the Midwest!

From there, head to Tahquamenon Falls State Park for a chance to spend a few hours gazing at striking waterfalls before heading to St. Ignace to hop on the ferry to Mackinac Island. After exploring the island, get ready to cross the Mackinac Bridge to Michigan’s Lower Peninsula, which is commonly dubbed “the mitten” because of its shape.

A must-visit spot in this area of the Midwest is the Headlands International Dark Sky Park for an unforgettable night of stargazing. If you get lucky, you might even get a glimpse of the northern lights!

After a night spent gawking at the stars, you’ll likely feel a bit hungry, so next on your itinerary is Traverse City, which is considered the foodie capital of Michigan! After gorging on as many dishes as you can, head over to Leland where you can explore Sleeping Bear Dunes National Lakeshore to end this epic Midwest road trip.

Bonus detour: If you have the time, make a small detour by driving the Leelanau Peninsula Wine Trail, where you’ll get to try the local wines at various estates. Can you think of a better way to close out this marvelous road trip?!

Longer to spend in Michigan? Check out some of the best beach towns along the Michigan coast, or our complete collection of scenic driving routes in Michigan

4. Iowa Nature Adventure

Even though the state of Iowa is often overlooked on most Midwest road trips, the Hawkeye State is actually a place that brims with natural gems if you just know where to look!

Start at Decorah’s Ice Cave, an ice cave you can explore in just a few minutes but acts as a super epic way to begin this Midwest road trip. From there, head over to Dunning’s Springs Park, where you’ll find a striking 200-feet waterfall hidden amid a charming forest.

Next on the itinerary is Effigy Mounds National Monument, which homes over 200 effigy mounds created by Native Americans centuries ago. Although American Indian ceremonial mounds can be found in several locations, Effigy Mounds National Monument harbors many that are shaped like animals!

Another natural highlight deserving a spot in your Iowa road trip is Maquoketa Caves State Park. Here, you can hike and explore tons of caves scattered throughout. Finish your trip at Wildcat Den State Park, where nature and history make a perfect mix that will allow you to hike to stunning geological formations on sandstone bluffs and learn about Iowa’s past at the Pine Creek Grist Mill.

5. Missouri Ghost Town Trail

If you’re a fan of the paranormal, this Missouri Ghost Town Road Trip is sure to please.

This unique scenic road trip will have you exploring some of the most haunted places in Missouri, some of which flourished when Route 66 was opened in 1926 and later abandoned when the interstates were built, and Route 66 was rerouted.

The first stop in this spooky Midwest road trip is Arlington, which was a thriving resort town back in the 1860s before it was forgotten and left to deteriorate. The town of Bloodland is next, which was abandoned during World War II and wiped out from the map, leaving only a church bell. Rumor has it that angry displaced residents have haunted the area ever since!

If you’re feeling brave, continue on I-44 until you find the only remains of Possum Trot, a church and a house that sit quietly eight miles southwest of Nixa, where ghost sightings have been reported time after time.

From here, head west to Monark Springs, a small town that was abandoned after a typhoid outbreak in the 1950s. Finally, end your spooky road trip in Georgia City, where the cemetery is all that remains from the once-prosperous town that thrived in the 1860s.

6. West Virginia Midland Trail

119 miles of pure wild beauty is what the West Virginia Midland Trail is all about.

Winding through rolling hills, dreamy forests, cascading waterfalls, and idyllic lakes, this scenic byway will take you from one end of West Virginia to the opposite, all while giving you plenty of opportunities to stop and park your car to go on a hike, see plenty of historic sites, and more.

Moreover, there are plenty of farmlands and small towns scattered all over that provide that old country charm. Hico, Ansted, Gauley Bridge, and Mt. Carbons are only some of the spots where you can stop and stretch your legs a bit, grab a bite, or spend the night before hopping back on your car and turning the music back on – preferably John Denver!

7. Milwaukee to the Wisconsin Dells

This is one of the best Midwest road trips for discovering the highlights of Wisconsin, taking you from Milwaukee to Green Bay and ending in the stunning Wisconsin Dells, one of the best family vacation spots in the Midwest.

Take in the highlights of Milwaukee from the food and breweries to its history and gallereis – don’t forget the Harey-Davidson Museum before hitting the road.

Following Lake Michigan to Green Bay you’ll pass through scenic towns such as Port Washington. Make sure to stop in at the Heritage Hill State Historical Park – and maybe catch a Green Bay Packers game?

The Wisconsin Dells await next – the kids will no doubt have their wishlist for “the Waterpark Capital of the World“, but there are plenty of other outdoor adventures to enjoy. Make some time for a scenic boat tour and try one of the many wineries, breweries and distilleries.

Devil’s Lake State Park is the perfect way to finish your Wisconsin Road Trip.

8. Iowa Great River Road

The Iowa portion of the Great River Road follows the great Mississippi River from Iowa’s northern to southern borders. Another classic Midwest road trip, this route will take you past beautiful landscapes such as farmlands, forests, and sheer bluffs where tons of eagles soar up high.

Along the way, you’ll also find many charming river towns with friendly people and interesting sites worth checking out. Think Al Capone’s hideout – the Julien Hotel in Dubuque – or Le Claire’s famous vintage shops, including the one featured in American Pickers!

Other points of interest along the Iowa Great River Road are Pikes Peak, the National Mississippi River Museum and Aquarium, Eagle Point Park, and the Dubuque Arboretum and Botanical Gardens.

9. Post-Rock Scenic Byway in Kansas

The Post Rock Scenic Byway is a stretch of byway in Kansas that winds through the Smoky Hills and Wilson Lake.

Even though it’s only 18 miles long, this route doesn’t slack in beautiful vistas and amazing points of interest. As a fun fact, the Post Rock Scenic Byway was named after the limestone rock posts used by Native Americans to build their homes and fences back in the day, some of which you can still admire today!

An important part of the Post-Rock Scenic Byway surrounds Lake Wilson, with many options for scenic stops and trails available for hiking in case you want to linger a while. At the end of the road trip, you’ll also get the chance to explore Lucas, an artistic small town that harbors several galleries and the well-known Garden of Eden, which features more than 150 statues!

Check out even more incredible Kansas scenic driving routes and byways over here

10. Old Red-Old Ten Scenic Byway in North Dakota

Running parallel to Interstate 94, the Old Red Trail will show you some of the best North Dakota has to offer, ranging from charming farm scenery to clear blue skies, vintage eateries, and quaint little shops filled with treasures to be found. This road is all about taking your time, driving slowly, and enjoying a ride that will make you feel as though you traveled back in time!

Once you pass Hebron, be on the lookout for the Richardton and Schnell Recreation Area, a 2,000-acre nature preserve where you can hit a few hiking trails in order to explore North Dakota’s unraveled nature. Other must-stops are Assumption Abbey in Richardton and Salem Sue, a giant Holstein Cow fiberglass sculpture.

11. Black Hills & Badlands in South Dakota

This family road trip includes some of the most iconic landmarks of the Midwest, and some of the most scenic drives.

A classic South Dakota road trip will see you start in Rapid City before traversing the incredible scenery and rugged beauty of Badlands National Park. Make sure to stop in at Wall Drug before venturing west to the Mammoth Site in Hot Springs.

Wind Cave National Park will be your next South Dakota stop. Explore one of the country’s oldest national parks with its fascinating and complex cave system.

Mount Rushmore, along with Crazy Horse Memorial are undoubtedly going to be your next stops. You can see the Presidents’ heads up close on the 0.6-mile Presidential Trail, a short trail walk, or seek out the overlook on SD-244 to see Washington’s profile from a distance. Come on a summer’s evening to witness “Legends in Light” laser light show on the Crazy Horse Memorial.

Make sure to finish your trip with the Peter Norbek Scenic Byway to experience the Cathedral Spires of Custer State Park, often regarded as one of the country’s best scenic byways.

12. Ohio Waterfall Road Trip

Last but not least, no trip to the Midwest is complete without exploring the stunning waterfalls of Ohio. The Ohio Waterfall Road Trip is the perfect route to take in order to explore the best of them!

Most of Ohio’s finest waterfalls can be found inside state parks, many of which you’ll get the chance to stop at as you drive this Midwest road trip. The Mohican State Park is a must-do stop where you’ll get the chance to see two falls, Big and Little Lyon Falls.

Next on the itinerary, head over to Cuyahoga National Park, where aside from getting plenty of incredible hiking ops, you’ll also get to see the striking 65-feet tall Brandywine Falls. You’ll find the best colors and climate in the fall.

To end your scenic drive in Ohio, drive over to Hocking Hills State Park, which harbors three gorgeous falls and a hiking trail that is commonly ranked as the best in the entire of Ohio!

We hope this list of the most epic Midwest road trips inspired you to grab your car keys, play some Johnny Cash tunes, and hit the road!

More To Know Before Hitting The Road In The Midwest

• Be careful of your time zones traveling through the Midwest! Michigan, Ohio, Kentucky, and Indiana follow Eastern time, whereas Wisconsin, Illinois, the Dakotas, Iowa, Kansas, and Missouri are in Central.

• Never forget an important road trip essential again! Download our family road trip checklist to help you pack for your next big adventure.

Which of these Midwest road trips catch your eye the most? I’d love to know which ones you’re most excited to drive, so let me know all about your plans in the comment section below!

Up Next:

Sensational Scenic Drives In The Deep South
6 Sensational Drives Not to Miss In Arkansas
Try These Terrific Day Trip Ideas From Chicago
You’ll Want to Undertake These Idyllic Indiana Road Trips

© Family Road Trip 2026

The post 12 Epic Midwest Family Road Trips appeared first on Family Road Trip.