The 25 Most Awesome Road Trips From Chicago: Day Trips, Weekend Getaways, and Longer Excursions!

short road trips from Chicago

Road trippers of Chicago, consider yourselves fortunate! A huge percentage of the USA is accessible within a 12-hour drive from the Windy City, so you can go just about anywhere in the Midwest or East Coast in just a day or two.

During my years living in Illinois, I took numerous road trips from Chicago. They included short trips to nearby cities like Milwaukee and Indianapolis, and longer drives to places like South Dakota and the Smoky Mountains.

Chicago may be the best city in America to take road trips from, so there are endless possibilities for car vacations. Even New York City and the west coast are within reach. It just depends how far you’re willing to drive and how much time you have!

chicago road trip options

Here, I’ve gathered 25 of the best road trips from the Chicago area for adventurous travelers. Some of these road trip suggestions will be obvious, like Indiana Dunes, Rockford, and Wisconsin Dells. Others may be destinations you’ve never considered, such as Ohio’s Amish Country and Kentucky’s Mammoth Cave National Park.

This list of trips from Chicago is broken down into short day trips, long weekend getaways, and extended 7- to 10-day excursions.

TIP: Before hitting the road, check our list of road trip necessities. Make sure to have a dash cam and emergency road kit! And here’s a post about the best food and snacks to take with you on the road.

ARTICLE CONTENTS:
Day Trips
Weekend Trips (2-4 Days)
Longer Trips (7-10 Days)

Day Trip Ideas From Chicago

1. South Bend, Indiana

studebaker museum

Roughly 95 miles from the Windy City, South Bend is an underrated choice for a day trip from Chicago. Notre Dame fans will enjoy checking out the campus and visiting the 125-year-old Basilica of the Sacred Heart.

Other South Bend activities include visiting the South Bend Chocolate Company, touring the Studebaker Museum, walking along the St. Joseph River, and seeing the flowers and succulents at Potawotami Conservatories.

A visit to South Bend can be combined with other destinations along the way, including Gary, Indiana (home of Michael Jackson’s birth home) and Indiana Dunes National Park along the shores of Lake Michigan.

2. Starved Rock State Park

starved rock day trip from chicago

Another of the best short road trips from Chicago is a day trip down to Starved Rock State Park. Virtually everyone who lives in Chicago and loves the outdoors has made this journey at least once.

Starved Rock has lots of hiking and camping opportunities, but it has so much more than that. There are waterfalls, sandstone cliffs along the river, and rock formations that are millions of years old.

Reserve your campground in advance because Starved Rock gets popular during the summer. If you’re so inclined, you could even ditch the vehicle and reach Starved Rock via a 108-mile bike route from Chicago. Who’s up for a bicycle road trip?

3. Rockford, Illinois

sock monkey statue

The fifth-largest city in Illinois, Rockford has come alive in recent years with new restaurants, businesses, and art galleries. Grab an outdoor table at Prairie Street Brewing Company and do some people watching along the Rock River.

Points of interest include the Discovery Center Museum, Anderson Japanese Gardens, and the Laurent House, a single-story home which was the only house Frank Lloyd Wright ever designed for an individual in a wheelchair.

For something quirkier, check out the Sock Monkey Museum and the sock monkey statues that are scattered around town. Hunt down the dozen fiberglass sculptures around town and take selfies with all of them!

4. Six Flags Great America

six flags chicago day trip

The quickest day trip from Chicago (and maybe the most fun!) is the one-hour drive to Six Flags Great America in Gurnee, Illinois. Visiting the park is expensive, but at least the drive is short enough that you can make it back home by night and not have to pay for a hotel.

The Superman coaster is my favorite because the seats hang from an overhead track, so you’re suspended with your arms out in front of you, just like Superman. Other favorites include the X Flight wing coaster, the Tornado water raft tunnel, the Revolution spinny ride, and the Maxx Force coaster.

5. Southern Michigan

southern michigan

Southern Michigan has a handful of spots along the lake that Chicagoans like to visit, including Grand Beach, New Buffalo, and Warren Dunes State Park. Find beaches, wine tasting, and small-town charm.

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The distance from Chicago to Michigan is only about 75 miles. That’s a drive of 90 minutes or so, depending on traffic.

Once during a rare mid-October heat wave, I took a quick road trip to Buchanan to stay at Fuller’s Resort, because it was the only campground still open. I got to chill out with virtually no crowds at bargain prices. As cheap road trips from Chicago go, it doesn’t get much more affordable than that!

6. Lake Geneva, Wisconsin

wisconsin strawberry farm

Just 90 minutes from Chicago, Lake Geneva is another touristy destination that offers outdoor recreation on the lake. Explore beaches, state parks, ziplining courses, and a 21-mile path around the lake.

You can rent kayaks wave runners, and even pontoon boats or powerboats! Spend a single day experiencing Lake Geneva, the town and the lake. Or spend a full weekend for a relaxing, upscale getaway from Chicago.

During the summer, I like to combine a trip to this part of Wisconsin with a stop off at the Thompson Strawberry Farm in Bristol. You pay $11 and get a 4-quart basket to select your own berries from the fields. It’s a great activity with your significant other!

Long Weekend Road Trips From Chicago

7. Nashville

nashville main street

Nashville, Tennessee is one of the most underrated cities in America, and you can get there from Chicago in less than 7 hours if you’re a fast driver.

For me, the big draw of Nashville is the music history. A lot of it centers on country music, including the Country Music Hall of Fame, the honky tonk bars of downtown Nashville, and RCA Studio B, where Elvis recorded many of his legendary songs.

The Music City Walk of Fame honors local legends from all genres, including Little Richard, Jack White, Michael McDonald, and Steve Winwood. Nashville has some of my favorite quirky attractions, including the Lane Motor Museum and the Dukes of Hazzard Museum.

There’s also a fair amount of American history in the Nashville area, including the Hermitage, Andrew Jackson’s former mansion, and the tomb of President James Polk.

8. Milwaukee, Madison, Kenosha

milwaukee day trip weekend getaway

I’ve done all three of these Wisconsin cities as separate day trips, but it’s much tidier to combine them into a weekend getaway. Kenosha has a surprising number of offbeat activities. One must-visit spot is the Jelly Belly Warehouse. Take a free tour and taste-test all of the company’s jelly bean flavors, including the weird ones like Toothpaste, Soap, and Dead Fish.

Milwaukee has numerous attractions, like the Public Museum, Harley Davidson Museum, the Fonzie Statue, and the uniquely-shaped Milwaukee Art Museum. Madison activities include visiting the university campus and state capitol buildings and exploring the Lakeshore Path.

From Madison, take the hour-long journey west to Spring Green to visit the House on the Rock. It’s hard to explain this place except to say it’s one of the kookiest attractions in America. Imagine a museum, funhouse, and hoarders’ mansion all rolled into one.

9. Amish Country, Ohio

amish country weekend trip from chicago

Find out how the Amish live and work during a visit to Berlin, Ohio, also known as Amish Country. This part of Ohio is home to the largest Amish population in America – even more than Lancaster, Pennsylvania.

While some of the Amish folks living here are wary of the growing influx of tourists, many locals rely on tourism dollars and welcome the visitors. You’ll find lots of guided tours, and hotels are plentiful.

Start at the Amish & Mennonite Heritage Center for background information about the Amish way of life and the people of the community. Make sure to visit Heini’s Cheese Chalet to choose from hundreds of varieties of homemade cheese. Stop into Boyd & Wurthmann for a hearty Amish meatloaf meal with pie for dessert.

10. Indiana Dunes National Park

indiana dunes national park

For years, the Indiana Dunes were a fun Chicago weekend getaway, and now the dunes have become a national park! That means they might be more crowded than in previous years, as national park junkies add the park to their wishlist.

The fun part of coming here is being able to play on the sand dunes. The dunes are located right on Lake Michigan, so you can go swimming if the weather cooperates. And on clear days you may even see the skyline of Chicago 50 miles away!

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The park also has some modest hiking and bike trails and some reasonably comfortable campgrounds, making this an affordable and cheap road trip from Chicago. It’s only 60 minutes away by car.

11. Minneapolis

spoonbridge and cherry

Another of my favorite Midwest cities is Minneapolis. (At least during the summer!) The drive here is 6 hours. Visit the cherry on a spoon sculpture at the Sculpture Garden, head over to the Mall of America for some shopping, check out the natural beauty of Minnehaha Falls, and visit the fascinating Mill City Museum.

Besides the attractions, I recommend just wandering around the neighborhoods and soaking in the friendly and cool vibe. Seek out a good restaurant and try a Juicy Lucy, a local favorite featuring cheese stuck inside the burger. Find a dive bar, do some thrift store shopping, and maybe visit a beach (they have several on the lakes).

12. Mammoth Cave National Park

mammoth cave best road trips from chicago

Too many Chicagoans overlook Kentucky’s Mammoth Cave National Park. It’s the longest cave system in the world, with more than 400 miles of naturally-formed underground passageways! The six-hour drive from Chicago is totally doable for a weekend trip.

Sign up for one of the affordable cave tours to get a look at the inside of the earth as you’ve never seen it before. I took the Domes & Dripstones Tour. The start of the tour was surreal, as we stood in a single-file line to enter a padlocked door that literally leads straight down into the earth.

After the first 51 man-made steps, the entire rest of the cave was formed naturally over millions of years. The experience is exploring this part of the earth’s upper crust is totally unique. More Midwesterners should consider giving Mammoth Cave a visit!

13. Olney, Illinois & Santa Claus, Indiana

olney illinois white squirrel

If you’re a fan of quirky roadside attractions like me, here’s an oddball Illinois road trip to consider. Have you ever heard of Olney? It’s a small town that for some reason has a large population of white albino squirrels. It’s so cool to watch white squirrels running around the streets and parks!

Meanwhile, Santa Claus is an Indiana city where it feels like Christmas all year long. Holiday World and Splashin’ Safari Water Park are holiday-themed amusement parks. If you’re not in the mood for roller coasters and thrill rides, head to the Santa Claus Christmas Store for quirky gifts or Santa’s Candy Castle, which has one of the most massive collections of sweets I’ve ever seen.

The drive time for me was about 11 hours. You can easily include a loop over to Indianapolis or Louisville, or pass through smaller towns like Terre Haute or Bloomington.

14. St. Louis

st. louis road trip near me

My first road trip from Chicago was to St. Louis. I actually made the trip as an ultra-cheap budget vacation using Megabus. But you can easily drive there in less than 5 hours, so it’s perfect for a weekend road trip.

I visited during a frigid February cold spell and still had a great time. St. Louis is a good place to visit any time of year because of its many indoor attractions. Head to the Gateway Arch (which is now a national park!) and the Budweiser Brewery. And make sure to check out the City Museum, one of the coolest playgrounds for both kids and adults.

15. Wisconsin Dells

wisconsin dells

Just three hours from Chicago, the Dells have been a popular summer getaway for many years. This area has everything you’d expect from a touristy vacation destination: museums, a casino, golf courses, go-karts, and duck boat rides on the river.

But the big attractions are the theme parks and waterparks. In fact, the Dells call themselves “the waterpark capital of the world.” Multiple resorts offer both indoor and outdoor waterparks, as well as indoor amusement parks. Imagine that – you and your friends can ride roller coasters and huge water slides even during the middle of winter!

16. Choose Your Own Rust Belt City Adventure

midwest road trip from chicago

The Midwest has several other medium-sized cities that are worth exploring. Take your pick between Indianapolis (3 hours driving time), Detroit (4.5 hours), Louisville (5 hours), Cleveland (5.5 hours), Columbus (5.5 hours), and Pittsburgh (7 hours.)

I’ve road tripped to all of these cities, and each has something unique to offer. Cleveland has the Rock and Roll Hall of Fame. Louisville has the Kentucky Derby Museum. My hometown of Pittsburgh has world-class museums like the Warhol and Heinz History Center. Cool Columbus activities include taking a Segway tour and exploring funky neighborhoods.

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Detroit’s urban revitalization continues with the Heidelberg Project and the venerable Motown Museum. And Indianapolis won me over with its Cultural Bike Trail and Indianapolis 500 Museum.

If you live in Chicago, love urban life, and you’re not comfortable getting on an airplane just yet, you could just literally visit a different one of these cities every weekend!

7- to 10-Day Road Trips From Chicago

17. Mount Rushmore/Badlands

mount rushmore road trip

One of my favorite Midwest road trips while living in Chicago was my drive to South Dakota. Everyone should see Mount Rushmore at least once! It’s one of the truly iconic American landmarks.

The giant Crazy Horse monument is a spectacle, and it’s not far from Rushmore. Custer State Park is a great place to see bison and wild burros.

Don’t miss Badlands National Park, one of the most unique landscapes in America. Think grasslands, swirling hills of rock, and prairie dogs. It’s a great place to go camping for a night or two.

Rushmore is roughly 934 miles from Chicago, so it’s best to take at least two days to get there. Sioux City, Iowa or Sioux Falls, South Dakota are ideal halfway points, depending on the route you take.

18. New York City (and Philadelphia)

statue of liberty

A road trip from Chicago to NYC is easier than you might think. The drive is less than 13 hours, so you can make it in one really long day (be sure to take turns driving!) Or take two-day drive and spend the night in Cleveland or Pittsburgh.

Once you arrive in the Big Apple, see the Statue of Liberty and the High Line, plus some of the city’s lesser-known attractions and the coolest NYC neighborhoods. Parking in Manhattan is crazy expensive and difficult. I’d suggest getting an Airbnb or hotel in Brooklyn and take the subway into the city.

On the way back home, set aside a day to swing down to Philadelphia, one of the most historic cities in America? Unique things to do in Philly include the Rocky statue and the Liberty Bell.

19. Great Smoky Mountains

smoky mountain park

Want to check out the most popular national park in America? The Great Smoky Mountains in Tennessee and North Carolina attract more than 11 million visitors annually.

Bring your hiking boots! Around 95% of the park is forested. That means 850 miles of hiking trails to choose from, including 70 miles of the Appalachian Trail. Keep an eye out for elk and black bears, and stop at some of the 100+ historic log cabins scattered around the park grounds.

The drive to the Smokies is about 9 hours from Chicago, so it can be done in one day. Consider staying in one of the touristy towns near the Smokies, such as Gatlinburg or Pigeon Forge.

20. Drive Part of Route 66

route 66 from chicago

Route 66 is considered one of the most classic drives in America. The iconic route begins in Chicago and runs all the way to the ocean in Santa Monica, California. You probably won’t have time to drive the whole thing. But you could at least do the 700 miles or so from Chicago through St. Louis to Tulsa, Oklahoma.

Add another 350 miles if you want get ambitious and make it to Amarillo, Texas to see the famous Cadillac Ranch art installation. A lot of the original highway is gone, but you can recreate most of the Route 66 route. You’ll see lots of small-town Americana and roadside attractions.

Be sure to visit Pops Soda Ranch in Oklahoma, which serves hundreds of different (and bizarre) flavors of soda pop.

21. Toronto & Niagara Falls

toronto chicago road trip

Chicagoans rarely consider Toronto, Canada as a road trip option, but it’s only 8 hours away if traffic and border crossings cooperate. Add another 90 minutes to reach Niagara Falls, one of the great natural wonders of North America.

Chicago and Toronto are incredibly similar. They have nearly identical-sized populations (around 2.7 million). Both have great museums, outdoor adventures, cultural experiences, culinary delights, and vibrant nightlife.

A few things Toronto has that Chicago doesn’t: The Hockey Hall of Fame, the CN Tower, and a chance to paddle in the Harbor Islands. For a silly tourist attraction, check out the Bata Shoe Museum.

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On the way to Toronto, you’ll pass through the town of London, Ontario, Canada. This city has lots of interesting attractions and fun things to do, so check it out!

22. Isle Royale National Park

isle royale national park

If you love outdoor adventure, kayaking, and hiking, then Isle Royale National Park is one of the best road trips from Chicago for you. Located on an island near the upper panhandle of Michigan, this trip requires a 7-hour drive to Houghton or Copper Harbor, Michigan.

From there, leave your car in a paid lot and take the ferry (book in advance!) across to the island. Isle Royale is one of the more remote national parks, which makes it relatively peaceful and quiet. The island has one hotel lodge, but everyone else settles in at one of the park’s campgrounds.

The island is 45 miles long by 9 miles wide, so it offers some incredible long-distance hiking opportunities. Be ready for possible moose sightings, as the isle has thousands in its forests.

23. New Orleans

driving to new orleans

Make sure to get your car tuned up before this one! The 14-hour, 926-mile trip to New Orleans is doable as a two-day drive (although I once had some crazy friends who drove the whole thing in one day after their flight was canceled!)

After such a lengthy drive, you’ll want to spend several days in the Big Easy, exploring New Orleans’ offbeat attractions and popular sights. Check out Mardi Gras World, explore the Faubourg Marigny neighborhood, get beignets at Café du Monde, visit the fantastic World War II Museum, and stop in to the Voodoo Museum and Pharmacy Museum.

Don’t forget to listen to some live jazz music. And then spend the night partying in the French Quarter. Few places in America can match the atmosphere of Bourbon Street!

24. Drive Part of Route 20

lewis clark road trip

U.S. Route 20 is the longest road in America, stretching from Boston to Newport, Oregon. It happens to pass through the southern end of Chicago. Driving all 3365 miles could take weeks, but you can pick a small portion of the road and start driving.

I once took 5 days to drive the portion of Route 20 from Chicago to Wyoming. This part of the route passes through Rockford and a bunch of small towns in Iowa and Nebraska. It’s not the most scenic drive in the country, but it provides a nice glimpse of small-town life.

Interesting attractions along the way include the Field of Dreams movie site and the largest museum in the world dedicated to clown dolls. How wonderfully strange!

25. Oklahoma, Kansas & Kansas City

oklahome road trip

Who would take a road trip from Chicago to Oklahoma and Kansas? *Raises hand* I did this exact trip a few years back. Why? Because I’d already visited the other places on this list, and my wanderlust could not be contained!

Plus, I love small towns and quirky roadside attractions. This trip landed first in Kansas City, Missouri, which has a ton of unusual sights, like the National Museum of Toys and Miniatures, the Arabia Steamboat Museum, and the world’s largest shuttlecocks.

From there, I proceeded to Kansas and explored Lawrence, Wichita, and Topeka. Highlights included the Brown vs Board of Education Historic Site, the Museum of World Treasures, and the Keeper of the Plains statue.

Oklahoma City, meanwhile, offered more offbeat fun, including a museum of animal skeletons, another dedicated to the banjo, and another all about cowboys and western life. This trip required around 7-8 days to complete.

Summary: It’s So Easy to Find Road Trips Near Me!

While living in Chicago, it was incredible that I had so many road trip destinations near me. This list doesn’t even cover them all.

Other possibilities include short Illinois road trips to places like Springfield, Champaign, and Peoria. The Abe Lincoln Home National Historical Site in Springfield is particularly noteworthy.

If you’ve got at least 5 days on your hands, consider other weekend trips from Chicago to Memphis, Atlanta, Charlotte, or Virginia Beach. Make this the summer of the road trip!

Do you have any other suggestions for great road trips from Chicago?

About Quirky Travel Guy

Scott Shetler is a Seattle-based freelance writer & fan of indie rock, road trips, ice cream, squirrels on power lines, runaway shopping carts, and six-way intersections. Some posts on this site contain affiliate links, which may earn me a commission (at no extra cost to you) if you make a purchase.

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