The 32 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 many years as a Chicago resident, I took numerous road trips from Chicago. As a road trip fanatic, I’ve personally done every drive on this list!

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 Gulf Coast are within reach. It just depends how far you’re willing to drive and how much time you have.

Here, I’ve gathered 32 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.

I’m covering everything from short road trips to nearby cities like Milwaukee and Indianapolis, to longer drives to places like South Dakota and the Smoky Mountains. Consult the list to plan your next getaway!

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

midwest road trips from chicago - route 66

We’ll start with the shorter drives, as most Chicagoans looking for road trips prefer something in the 3- to 5-hour range. For each destination, I’ve included the driving time and a recommended hotel.

Day Trips From Chicago
Weekend Getaways (2-4 Days)
Longer Road Trips From Chicago (7-10 Days)

Day Trip Ideas From Chicago

1. South Bend, Indiana

Distance: 95 miles
Drive Time: 1 hour, 35 minutes
Where to Stay: Ivy Court Inn & Suites
More Info: Visit South Bend & Mishawaka, IN

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.

The Basilica is an incredibly impressive old church with gorgeous stained glass and high ceilings with large murals. While it’s an active place of worship, the Basilica encourages respectful visits from guests eager to admire the art and architecture as well.

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 Michael Jackson’s birth home in Gary, and Indiana Dunes National Park along the shores of Lake Michigan.

2. Starved Rock State Park

Distance: 92 miles
Drive Time: 1 hour, 35 minutes
Where to Stay: Holiday Inn Ottawa
More Info: 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. The park is known for its 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. Take the 4-mile round-trip hike to see the waterfalls at French, Wildcat, and LaSalle Canyons.

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

Distance: 89 miles
Drive Time: 1 hour, 34 minutes
Where to Stay: Staybridge Suites
More Info: Welcome to Rockford IL

sock monkey statue

Before visiting, I didn’t know much about Rockford except that Rock and Roll Hall of Fame drummer Bun E. Carlos of Cheap Trick grew up there. But I was impressed with the city during my stay!

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. Springfield, Illinois

Distance: 202 miles
Drive Time: 3 hours, 10 minutes
Where to Stay: President Lincoln Doubletree Hotel
More Info: Visit Springfield Illinois

springfield - midwest day trips from chicago
Springfield is one of the easiest day trips from Chicago.

The capital city of Illinois, Springfield is about 3 hours from Chicago, so it’s either a really long day trip, or a nice overnight journey.

You can tour the State Capitol building, as well as the Old State Capitol Building (which served from 1839-1876.) This city has so many historic buildings that you’ll need a full day to see them all.

The real attraction here is all the Abraham Lincoln history. You can see his tomb at Oak Ridge Cemetery, and the Lincoln Home National Historic Site, the very house he lived in before becoming president.

It’s rare to get a glimpse into the personal life of such an important historic figure like President Lincoln, so make sure to take the house tour!

I loved visiting the Lincoln Presidential Library as well. The library provides so much context and detail about Lincoln’s life and achievements that even folks who consider themselves history buffs will learn a lot.

5. Southern Michigan

Distance: 75 miles
Drive Time: 1 hour, 25 minutes
Where to Stay: Lakeside Inn
More Info: Southwestern Michigan Tourist Council

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.

Exploring the sand dunes of Lake Michigan is a lot of fun. 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 in the forest 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

Distance: 83 miles
Drive Time: 1 hour, 30 minutes
Where to Stay: Grand Geneva Resort and Spa
More Info: Visit Lake Geneva WI

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.

Lake Geneva is a good family destination, with waterparks, zipline courses, and a drive-thru safari adventure. that will allow you to see giraffes, zebras, ostrich, and camels up close without leaving your vehicle!

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!

7. Casey, Illinois – Town of Giant Things

Distance: 210 miles
Drive Time: 3 hours, 15 minutes
Where to Stay: Days Inn & Suites
More Info: Casey, Illinois Tourism

casey illinois giant things

Casey, Illinois is a small town known for big things. Like, really big things. Such as the world’s largest rocking chair.

Casey has more than a dozen official “world’s largest” attractions, and several other giant things as well. You’ll see a giant mailbox, a giant golf driver, a giant taco, a giant mousetrap, a giant pizza cutter, and much more.

If you love fun roadside attractions as much as I do, you should definitely visit the town of Casey at least once!

Casey is a little over 3 hours from Chicago, so it’s a long day trip, but you can make it work. The university city Champaign is about halfway to Casey, so you can swing through there as well.

8. Six Flags Great America

Distance: 45 miles
Drive Time: 50 minutes
Where to Stay: Wingate by Wyndham
More Info: 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, if you’re so inclined.

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.

They’re always adding new stuff, so they will probably have several new rides by the time you read this – like the Sky Striker rotating pendulum ride, which opens in 2024.

Six Flags is an easy day trip during the summer months, and it’s one of the top amusement parks in the country!

Long Weekend Road Trips From Chicago

9. Nashville

Distance: 470 miles
Drive Time: 7 hours, 15 minutes
Where to Stay: Moxy Nashville Downtown
More Info: Visit Music City

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.

You can take a backstage tour of the Grand Ole Opry. There’s also the National Museum of African American Music. 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.

Not sure what to do? Get a good introduction to the city with the Nashville Hop-On, Hop-Off Trolley that takes visitors all around town.

If you want to explore a fun but smaller city, go another two hours south to Chattanooga, which has historic sites and outstanding outdoor adventures such as hiking and kayaking.

10. Wisconsin Road Trip Loop: Kenosha, Milwaukee, Madison, Spring Green

Distance: 92 miles to Milwaukee; 147 miles to Madison
Drive Time: 1 hour, 30 minutes to Milwaukee; 2 hours, 25 minutes to Madison
Where to Stay: Saint Kate Arts Hotel (Milwaukee); Hotel Indigo (Madison)
More Info: Visit Milwaukee, Visit Madison

milwaukee day trip weekend getaway
Milwaukee is another good road trip destination from the Windy City.

I’ve done all four of these Wisconsin cities as separate day trips, but it’s much tidier to combine them into a weekend getaway.

Start by heading north to Kenosha, then proceed up to Milwaukee. After staying overnight there, go to the state capital of Madison, and then head further west to Spring Green. From there, drive back to Chicago.

It’s about 7.5 hours of total driving, with four cool stops on the way. Here’s what the driving route would look like:

chicago to wisconsin road trip map
Chicago to Wisconsin – Midwest road trip map (Google)

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 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. Everyone should visit the House on the Rock once.

11. Amish Country, Ohio

Distance: 367 miles
Drive Time: 6 hours, 10 minutes
Where to Stay: Berlin Heritage Inn
More Info: Visit Berlin, OH

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 activities aimed at visitors, and hotels are plentiful.

Finding authentic Amish experiences isn’t as difficult as you may think. Berlin has a number of guided tours that allow you to meet with and interact with Amish locals.

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, and make sure to save room for dessert. Their old-fashioned pies are delicious!

12. Indiana Dunes National Park

Distance: 38 miles
Drive Time: 50 minutes
Where to Stay: Spring House Inn
More Info: Indiana Dunes National Park (U.S. National Park Service)

indiana dunes national park - weekend getaways and day trips from chicago

For years, the Indiana Dunes have been a fun Chicago weekend getaway, and now the dunes have officially become a national park!

That means they’re more crowded than in previous years, as national park junkies add the park to their vacation 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!

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.

You could certainly do Indiana Dunes NP as a day trip, since it’s less than an hour from Chicago. But since it’s an actual national park, I suggest staying overnight to give yourself more time to explore.

13. Minneapolis

Distance: 410 miles
Drive Time: 6 hours, 10 minutes
Where to Stay: Millennium Minneapolis
More Info: Meet Minneapolis

spoonbridge and cherry
Minneapolis is one of the most underrated Midwest road trips from Chicago.

I absolutely love Minneapolis. It’s another of my favorite Midwest cities – 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.

While you’re at the Mall of America, consider the SEA LIFE Minnesota Aquarium, which houses all the underwater wildlife you could possibly want to see.

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).

14. Mammoth Cave National Park

Distance: 386 miles
Drive Time: 6 hours
Where to Stay: Grand Victorian Inn
More Info: Mammoth Cave National Park (U.S. National Park Service)

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’ve taken two different tours here, but I especially enjoyed 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!

15. Olney, Illinois & Santa Claus, Indiana

Distance: 245 miles to Olney; 323 miles to Santa Claus
Drive Time: 3 hours, 50 minutes to Olney; 5 hours, 30 minutes to Santa Claus
Where to Stay: Best Western Plus (Olney); Santa’s Lodge (Santa Claus)
More Info: Olney, IL Tourism; 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.

16. St. Louis

Distance: 297 miles
Drive Time: 4 hours, 30 minutes
Where to Stay: Angad Arts Hotel
More Info: Explore St. Louis

st. louis road trip near me

My first-ever 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’ve visited in the middle of summer, and during a frigid February cold spell, and always 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!) for a bird’s eye view of the city. Stop in to the Budweiser Brewery to learn how the iconic brand brews its beverages and to see the Clydesdale horses up close.

Make sure to check out the City Museum, one of the coolest playgrounds for both kids and adults. And spend some time in the vibrant Delmar Loop neighborhood.

St. Louis is right on Route 66, so you can drive from Chicago to St. Louis via the historic highway and see pieces of the original road!

17. Wisconsin Dells

Distance: 195 miles
Drive Time: 3 hours, 5 minutes
Where to Stay: Aloha Beach Resort
More Info: Official Site For Wisconsin Dells

wisconsin dells - midwest road trips from chicago

Just three hours from Chicago, the Wisconsin 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!

If you’re looking for something less touristy, nearby Devils Lake State Park offers scenic hiking and lake adventures away from the kids’ parks.

18. Columbus, Ohio

Distance: 356 miles
Drive Time: 5 hours, 35 minutes
Where to Stay: The Urban
More Info: Experience Columbus

midwest road trip from chicago

Items #18-23 on this list are basically a “choose your own Rust Belt city” adventure. Take your pick between all of the medium-sized cities in the Midwest that have something unique to offer. If you live in Chicago and love urban life, you could just literally visit a different one of these cities every weekend!

Let’s start with Columbus, Ohio. It’s a modern, vibrant city with a lot to do. Cool Columbus activities include visiting the Book Loft, the North Market, Jeni’s Ice Cream, and 16-Bit Bar and Arcade.

Columbus is also a fun place to take a Segway tour to explore its funky neighborhoods. And make sure to see the Arnold Schwarzenegger statue, which depicts the former California governor in a bodybuilding pose.

19. Louisville, Kentucky

Distance: 300 miles
Drive Time: 4 hours, 45 minutes
Where to Stay: Galt House Hotel
More Info: Louisville Tourism

kentucky derby museum - louisville road trip

I’ve been to Louisville twice now and was surprised how much I enjoyed the city. Louisville is the home of Churchill Downs, site of the famous Kentucky Derby. You can walk onto the race track itself when you visit the Kentucky Derby Museum.

Even if you’re not a horse racing fan, getting to learn about the history and majesty of the event is pretty cool.

Louisville has a few other noteworthy attractions. The Muhammad Ali Center is a museum about the boxer’s life and career, plus his dedication to humanitarian efforts. It does a great job of explaining that causes that Ali spent his life fighting for.

Downtown Louisville also has two giant attractions that are both the world’s largest bat. One is a 120-foot-tall baseball bat outside the Louisville Slugger Museum. The other is a giant vampire bat hanging on a wall outside Caufield’s Novelty store.

20. Pittsburgh

Distance: 461 miles
Drive Time: 7 hours, 10 minutes
Where to Stay: Priory Hotel
More Info: Visit Pittsburgh

warhol museum pittsburgh

I could go on for hours about all the awesome things to do in my hometown of Pittsburgh. The city has world-class museums like the Warhol and Heinz History Center.

Pittsburgh is the home of the National Aviary, which features dozens of bird species from around the world. It also has two famous inclines which carry passengers to the top of Mount Washington to the viewpoints overlooking the city.

Grab food and a drink in the South Side neighborhood, attend a Steelers game (if you can get tickets), and see the Nationality Rooms at the University of Pittsburgh’s Cathedral of Learning.

You can reach Pittsburgh from Chicago in about 7 hours and still have plenty of time for a full weekend exploring all of the city’s highlights.

21. Detroit

Distance: 285 miles
Drive Time: 4 hours, 15 minutes
Where to Stay: The Inn on Ferry Street
More Info: Visit Detroit

hart plaza detroit

Detroit’s steady urban revitalization is continuing. The city has a lot of fun things to do, starting with the venerable Motown Museum.

Also known as Hitsville USA, the Motown Museum occupies the very building where the Jackson 5, Stevie Wonder, Diana Ross, and the other great singers of the Motown era recorded many of their biggest hits. It’s open for daily tours.

The Heidelberg Project is a unique neighborhood art project that tourists should check out.

Meanwhile, in the suburb of Dearborn, the Henry Ford Museum has a collection of presidential limousines from over the years, and lots of other old Ford vehicles from the past 100-plus years.

22. Indianapolis

Distance: 182 miles
Drive Time: 3 hours, 15 minutes
Where to Stay: The Alexander
More Info: Visit Indy

indy motor speedway - midwest road trips

Just over three hours from the Windy City, Indianapolis is another overlooked Midwest road trip option from Chicago.

Indy won me over with its Cultural Bike Trail, an 8-mile path connecting downtown with some of the cool neighborhoods surrounding it. If you don’t have the ability to bring your own bike from Chicago, you can find one to rent here.

The Indiana state capitol building, the NCAA Hall of Champions, and the Native American-centric Eiteljorg Museum are among the places you can reach via the bike path.

Another big highlight in the city is the Indianapolis 500 Museum. You can see some of the cars that have won the famous race, and even step out onto the track yourself.

One of the city’s coolest spots is 100 Acres Park, a sculpture park outside the Indianapolis Museum of Art. See the cool art inside the Alexander Hotel. And the Indianapolis Zoo has a number of interesting programs.

23. Cleveland

Distance: 345 miles
Drive Time: 5 hours, 30 minutes
Where to Stay: Westin Cleveland Downtown
More Info: Cleveland, OH Tourism

free stamp cleveland - chicago weekend getaways

Cleveland has the Rock and Roll Hall of Fame. That’s reason alone to visit! I can spend an entire day inside the Rock Hall, looking at its exhibits, memorabilia, and interactive displays related to the greatest musicmakers of the last 75 years.

In Cleveland, I suggest staying at the Westin, one of the best hotels near the Rock and Roll Hall of Fame.

The Rock Hall isn’t the only attraction here. Other quirky and unique things to do in Cleveland include the A Christmas Story House, a museum dedicated to the classic holiday movie; the giant ‘FREE’ stamp; the Cleveland Police Museum; President Garfield’s tomb at Lake View Cemetery; and the Sweetie Candy Company.

Fun footnote for road trippers: Cleveland sits on U.S. Route 20, the longest road in America.

7- to 10-Day Road Trips From Chicago

24. Mount Rushmore/Badlands

Distance: 933 miles
Drive Time: 10 hours, 50 minutes
Where to Stay: Lodge at Palmer Gulch
More Info: Mount Rushmore National Memorial; Badlands National Park

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.

25. New York City (and Philadelphia)

Distance: 790 miles
Drive Time: 12 hours, 20 minutes
Where to Stay: Hotel 57 (NYC); Penn’s View Hotel (Philadelphia)
More Info: NYC Tourism; Visit Philly

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 a 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, the Liberty Bell, and City Hall Tower.

26. Great Smoky Mountains

Distance: 576 miles
Drive Time: 9 hours, 10 minutes
Where to Stay: Edgewater Hotel (Gatlinburg)
More Info: Great Smoky Mountains National Park (U.S. National Park Service)

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.

27. Drive Part of Route 66

Distance: Varies
Drive Time: Varies
Where to Stay: Angad Arts Hotel (St. Louis); Stoney Creek Hotel (Tulsa)
More Info: U.S. Route 66 – Wikipedia

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 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.

28. Toronto & Niagara Falls

Distance: 515 miles
Drive Time: 7 hours, 50 minutes
Where to Stay: InterContinental Toronto
More Info: Destination Toronto

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.

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!

29. Isle Royale National Park

Distance: 460 miles
Drive Time: 7 hours, 45 minutes
Where to Stay: Rock Harbor Lodge
More Info: Isle Royale National Park (U.S. National Park Service)

isle royale national park
One of my personal favorite road trips from Chicago is gorgeous Isle Royale in Michigan.

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. Be sure to book your trip a few months in advance, since the ferries and park hotels/campgrounds can sell out well ahead of time.

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.

30. New Orleans

Distance: 925 miles
Drive Time: 13 hours, 45 minutes
Where to Stay: Le Meridien
More Info: Visit New Orleans

driving to new orleans

Make sure to get your car tuned up before this one! The 14-hour, 925-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 colorful 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!

31. Drive West on Part of Route 20

Distance: Varies
Drive Time: Varies
Where to Stay: Hilton Garden Inn Riverfront (Sioux City, IA)
More Info: U.S. Route 20 – The Longest Road in America

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, and some Lewis & Clark exploration historical markers.

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

32. Oklahoma, Kansas & Kansas City

Distance: 510 miles to Kansas City; 790 miles to Oklahoma City
Drive Time: 7 hours, 45 minutes to Kansas City; 11 hours, 50 minutes to Oklahoma City
Where to Stay: Crossroads Hotel (Kansas City); Colcord Hotel (Oklahoma City)
More Info: Visit KC; Visit Oklahoma 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 do a mini Kansas road trip 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 days to complete, and it was an awesome experience in a part of the country not a lot of people visit!

Tips and Things To Keep in Mind for Road Trips Near Chicago

chicago road trip options

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 Galena, Champaign, Bloomington, Normal, and Peoria.

The University of Illinois campus in Champaign is particularly noteworthy. Galena is home to statues of Ulysses Grant and his wife Julia.

For any car journey, before hitting the road, check our list of road trip necessities. Make sure to have a dash cam and emergency road kit!

Here’s a post about the best food and snacks to take with you on the road, and here’s my playlist of the best songs about driving!

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!

And if you want to get really crazy, here’s a detailed guide to driving from Chicago to Seattle (you’ll need about a week each way), and another from Chicago to Banff National Park in Canada!

Do you have any other suggestions for great road trips from Chicago? Leave a comment and let us know!