6 Best Illinois Road Trips

Illinois is the starting point for many memorable road trips. Whether it’s city cruising through the streets of Chicago or travelling back in time on historic Route 66, there’s an adventure for everyone in the Prairie State.

From forests and plains to towering skyscrapers, Illinois has a variety of sights, stops and attractions to keep you entertained on the road.

Wondering where to start? Take a look at our hand-picked road trips to help you plan the perfect route. If you love movies, try out our filming locations tour. Or if history is more your thing, we have a roaring twenties trip filled with gangster hangouts, old-school diners and plenty of jazz.

Check out the Hertz road trip planner to find your next adventure or take a look at some of our favourite road trips in Illinois below.

1. Illinois to Illinois: Roaring Twenties Chicago

H3: 300 miles, 3 days, 14 stops

Throw yourself into the world of bootleggers, gangsters and all that jazz with our Roaring Twenties road trip around Chicago.

First, you’ll take a drive down Route 66. Built in the 1920s, this iconic highway has been the inspiration for American road trips throughout the last century – so it’s only right you start your trip here too.

As you weave in and out of the city, stop at legendary landmarks like the Chicago Theatre, Willis Tower and Wrigley Field. Grab something to eat along the way at notorious 1920s dining spots like Lou Mitchell’s – serving all-day breakfasts since 1923 – and the Chicago Pizza and Oven Grinder – a lookout spot for the St Valentine’s Day Massacre of 1929.  

With a trip this classic, you’ll need a car to match. Reserve a sleek convertible with Hertz, such as the Ford Mustang GT or a Porsche Boxter.

Experience the Roaring Twenties

2. Illinois to California: Getting Your Kicks

2,062 miles, 14 days, 14 stops

Fancy exploring beyond Chicago? Then it’s time to hit Route 66 for a tour of America’s early settlements, desert landscapes and quirky rest stops.

Start on the Illinois border at the Cahokia Mounds Historic Site and follow the famous road to natural wonders like the Fantastic Caverns and Palo Duro Canyon, as well as popular family activities like Tulsa Zoo.

Along the way, check out the charming roadside attractions. Browse for souvenirs at Nelson’s Old Riverton Store, stop for classic Texan food in Amarillo and learn about the route’s history at the Route 66 Museum in Kingman, California.

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3. New York to Illinois: Grit, Gangsters and Gasoline

1,283 miles, 10 days, 12 stops

Get to grips with some of America’s most famous gangsters with our road trip exploring the hidden underworld of the Eastern seaboard.

Starting in New York, this route will take you to popular gangster movie location – St. Patrick’s Old Cathedral – as well as Eastern State Penitentiary, where the likes of Al Capone were incarcerated.

Keep your wits about you as you venture to the Gothic-looking Ohio State Reformatory – where The Shawshank Redemption was filmed – and the appropriately named Helltown. Both are well-known for their paranormal sightings, so why not stop for a ghost tour if you’re feeling brave?

Then it’s back on the road to our final stop in Chicago. Hop aboard the ‘Gangster bus’ for an Untouchable Tour of the city. Get a close up of hoodlum hangouts, back-alley gambling dens, speakeasys and even a few gangland shooting sites. Finding out more about the gangs of the early 20^th century rounds off an incredible historic road trip.

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4. Missouri to Kansas: Best of the Midwest

1,433 miles, 10 days, 12 stops

The Midwest has a lot to offer, and this road trip incorporates history, culture, and family adventure to offer up an exciting journey through the best of the region.

Illinois has three stops on this trip, starting at the Lincoln Home National Historic Site. Take a tour of the Lincoln home and see where President Lincoln lived and worked. There are tours and educational programs held throughout the year.

Next, head over to the Bloomington Constitution Trail, a bike trail that was opened in 1987 and offers some of the most wonderful scenery in the area. Hire a bike to get around and read the signs on the trail to learn more about the Constitution and the founding fathers.

Your last stop in Illinois is arguably the coolest – the Wicker Park Secret Agent Supply Co. Stock up on spy-related gifts and gadgets at this funky little store, and help the children of Chicago with their creative pursuits as every purchase includes a donation to 826CHI’s free writing program.

Discover the Best of the Midwest

5. Montana to Cleveland: Interstate 90

1,957 miles, 12 days, 13 stops

Interstate 90 passes straight across Illinois’s northern border, making it the ideal route for a east-west road trip. Starting in Montana, the highway takes you through some of North Central America’s most amazing historical and natural sights.

Follow one of three scenic byways past mountain lakes and alpine meadows in Bighorn National Forest, then it’s on to Mount Rushmore and Minneapolis Sculpture Park for close-up view of the region’s most iconic carvings and creations.

You’ll find two stops in Illinois on this road trip. Firstly, at Myopic Books – a popular second-hand bookstore that stocks more than 70,000 books from floor to ceiling. It’s an absolute treasure trove for book lovers. And secondly, Oz Park for a family day-out with Dorothy, the Tin Man, Scarecrow and Lion.  

Then, it’s back on the I-90 into Ohio for a trip to Cleveland’s industrial 78^th Street Studios and classical Museum of Art.

Hit the Interstate 90

6. New York to Minnesota: Filming Locations

1,657 miles, 11 days, 12 stops

Take this road trip to see some of your favorite filming locations, from Ghostbusters and Rocky, to Night of the Living Dead. Movie buffs will thoroughly enjoy this journey through some of the most iconic East Coast film sets.

Drive like a movie star in your very own Ford Mustang as you make your way to iconic settings, like Katz’s Deli in When Harry Met Sally and Blairtown from Friday the 13th. 

Love a zombie movie? You’re in luck. The filming locations for both Dawn of the Dead and its prequel, Night of the Living Dead, are within an hour’s drive of each other – so you can easily see both on this tour.

And did you know Groundhog Day was filmed in Woodstock, Illinois? Take a stroll around the main streets to walk in Bill Murray’s footsteps and check out the plaques dotted around town to find out more about the filming process. It’s a lovely stop on the tour and hopefully you’ll be able to get out of Woodstock without having to repeat the day.

Explore iconic Filming Locations

With cities and natural wonders set side by side, there is so much to see in Illinois. That’s why we recommend planning a road trip to see the Prairie State in all its glory.

Reserve your Illinois rental car with Hertz to get around stress-free and in style.