12 Short & Long Road Trips From Chicago | Budget Car Rental

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Although you’ll never have a shortage of things to do in Chicago, a change of scenery can hit the spot when city life starts to feel harried. 

No car? No problem. If you need to escape the city for the beauty of nature, rent a car from Budget and head north to Wisconsin or south to Shawnee National Forest. Budget minivan rentals make it easy to take your family on a tour of Route 66, which begins in the Windy City. 

Plan a Chicago-based road trip today with the help of our suggestions below. You’ll find inspiration for day trips, weekend getaways, week-long escapes, and month-long adventures. Don’t forget to reserve a car at one of the convenient Budget locations in Chicago

Day Trips


1. Oak Park, Illinois


Drive time: 30 minutes from downtown

Best for: Architecture enthusiasts

Oak Park is barely outside Chicago proper, but it’s a great place to spend an afternoon. Get around easily when you take a rental car to this west side hub known as the longtime home to Frank Lloyd Wright. Elsewhere in the neighborhood, stop by the birthplace of Ernest Hemingway. Grab some local eats and sweets before heading back to the city.

2. South Bend, Indiana

Drive time: about 2 hours from downtown

Best for: Fighting Irish fans and car lovers

Anyone who’s ever rooted for Notre Dame from afar deserves to watch the Fighting Irish in person—or at least walk around the beautiful campus if you can’t score tickets to a home game at the stadium. 

Of course, the city has much more to offer, including several niche museums. If you have any interest in automotive history, don’t miss the Studebaker National Museum.


3. New Glarus, Wisconsin


Drive time: 3 hours from downtown

Best for: Beer lovers and Santa believers

Get ready to hear “Willkommen” when you enter the town of New Glarus, “America’s Little Switzerland.” If you’re coming to the area for a Wisconsin brewery tour, rent an economy car from Budget right at O’Hare and head north to sample custom beers from the impressive New Glarus Brewing Company. 

Got little ones? Rent a Budget minivan to celebrate St. Nicholas Day and have lunch with Santa Claus in December.

Weekend Getaways

4. Starved Rock State Park

Drive time: 2 hours from downtown

Best for: Family fun or a romantic rendezvous

If you want to encourage a little less screen time during the summer break, take your family to explore the great outdoors in a Budget rental. One of the best places to visit in Illinois, this state park features 18 canyons and 13 miles of hiking trails to explore. Entrance to Starved Rock State Park is free, making this a budget-friendly trip. 

More interested in a romantic winter outing? Pack plenty of layers and load into a luxury SUV for a weekend of cross-country skiing, hot cocoa, and the spa-like amenities of Starved Rock Lodge.


5. Lake Geneva, Wisconsin 


Drive time: 2 hours from downtown

Best for: Outdoor adventurers and business retreats

Spending time outdoors doesn’t always mean pure peace and quiet. This year-round resort offers visitors a chance to adventure on ziplines, play on the beach, or ski the nearby slopes. After you play, unwind at a spa or visit a local winery. Lake Geneva is equally suited to host groups of friends and company events. Either way, an SUV or passenger van rental from Budget can get your entire party there together. 

6. Bloomington, Indiana 


Drive time: 4 hours from downtown

Best for: Hoosiers at heart

Got a high school student interested in becoming a Hoosier? Schedule a campus tour at the Indiana University campus in Bloomington. Visit in early winter to make sure you see the men’s basketball team play at Branch McCracken Court. For other tastes of campus life, catch a showing at IU Cinema, grab a drink at Crumble Coffee, and add to your LP collection at Landlocked Music.

One-Week Vacations

7. South Haven, Michigan

Drive time: 2 and a half hours from downtown

Best for: Summer escapes

Summer is the perfect time to drive around Lake Michigan to South Haven (although the town has activities during all seasons). South Haven’s slow pace invites you to leave the hustle and bustle of the city behind and enjoy quality time with family. Pick your own blueberries, visit a lighthouse, take a bike ride—just enjoy the slower pace of life. Pack your minivan rental with beach gear and get on the road!


8. Cahokia Mounds State Historic Site


Drive time: 5 hours from downtown

Best for: Native American history mavens

Across the Mississippi River from St. Louis, Illinois has its own landmark. Cahokia Mounds is the site of a once-thriving Native American city. Archaeologists have studied the area for decades and uncovered evidence of a complex society. Visit the Cahokia Museum and Interpretive Center before trekking to the top of Monks Hood and the sun calendar Woodhenge.  

9. Quincy, Illinois 


Drive time: 5 and a half hours from downtown

Best for: History buffs

You’ll feel like you’re in a time machine during your visit to Quincy. In this city on the Illinois-Missouri border, you can tour a castle built in 1900, trek to a Lincoln-era log cabin village, learn about military history at the All Wars Museum, and see the Eells House, a stop on the Underground Railroad. Multiple area hotels and campgrounds make Quincy a great place to take a week-long getaway. Don’t leave without treating yourself to a pastry at Underbrink’s Bakery.

Month-Long Road Trips

10. Illinois’s Great River Road


Drive time: 3 and a half hours from downtown to East Dubuque

Best for: True Midwesterners

Take a family road trip along the huge Mississippi River. In Illinois, the Great River Road follows this famous American waterway from East Dubuque in the north to Cairo in the south. Any portion of the road between East Dubuque and Nauvoo is perfect for Chicagoans or tourists renting a car at Midway airport

In East Dubuque and Galena in northern Illinois, visit a residence that belonged to President Ulysses S. Grant, or take your train-obsessed kiddo to the Chicago Great Western Railway Depot Museum. Along the Mississippi’s brief horizontal jog, Moline and Rock Island offer visitors more fun. The John Deere Pavilion features simulated driving experiences of some huge farm machines. If it’s an adults-only trip, stop by Jumer’s Casino and try your luck. In the Nauvoo area, visit the city’s many historic homes to get a taste of life in this 19th century Mormon settlement.

11. Shawnee National Forest

Drive time: 6 hours from downtown

Best for: Nature lovers

Find acres upon acres of natural beauty at Shawnee National Forest. This 6-hour trip from Chicago is more than worth the journey, thanks to the trees, lakes, and hills that await you. Bring all the camping gear your SUV or truck rental will carry so you can stay as long as you please.

Must-see sights in the forest include: 

  • The Garden of the Gods, with unique rock formations like Camel Rock and Anvil Rock

  • Bell Smith Springs, where you can hike moderate trails over creeks and through canyons

  • Little Grand Canyon, which features a 3-mile trail perfect for experienced hikers

  • Inspiration Point, a limestone bluff and overlook point where you can view prairie grass, the Mississippi River, and lush forests

On any visit to Shawnee National Forest, be prepared to avoid poison ivy and stay well-protected from the sun. Carry some binoculars, too, in case you spot a bald eagle.


12. Route 66 in Illinois


Recommended pace: 60-80 miles per day

Best for: Bucket-listers and Lincoln lovers

There’s plenty to see, do, and eat along Route 66 in Illinois. The best part about this road trip? The Mother Road begins in Chicago, so snap your first selfie of the trip by the official sign at East Adams and South Michigan Avenue. 

From there, hop in your car rental and head for Wilmington, home of the Gemini Giant. This 28-foot statue overlooks a delicious drive-in called The Launching Pad where you can stop for lunch. When you need a walk to stretch your legs, visit the 20 murals in downtown Pontiac or the 1940s billboards in Lexington. 

Once you reach the state capital, pay your respects to the 16th president. Abraham Lincoln, his wife, and three of their sons are buried in Springfield beneath a memorial obelisk. Springfield also houses the Lincoln Presidential Library. 

If you travel for a whole month, you can easily make it to the Pacific Ocean and the end of the road in Santa Monica, CA. No matter how many miles you cover, though, this is one trip that is about the journey, not the destination. Make sure you choose a spacious vehicle in the Budget fleet so you have plenty of room to stretch out on this incredible road trip.

Turn Your Road Trip Dream Into a Reality With a Car Rental

No matter how far you choose to travel from Chicago, you’ll need a reliable vehicle to get you where you need to go. Pick up a rental car from Budget so you can comfortably and confidently drive to your final destination.


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