Leave the skyscrapers and city traffic behind and enjoy the great outdoors around the Midwest, where you can experience expansive lakes and sandy dunes — weather permitting, of course. Although Route 66 begins in downtown Chicago, we’re focusing on road trips from Chicago that are a bit more manageable, so you’ll spend fewer hours behind the wheel and have more time to enjoy the destination.
While Avail does make it easy to borrow a vehicle for more than a day, you won’t need to reserve a long-term car rental to make one of these trips.
Quick weekend road trips from Chicago
Because of the many highways that loop around and cut through Chicago, it’s incredibly easy to hit the road. Renting a car for a road trip saves mileage on your personal vehicle. But if you don’t have one, it helps you easily escape the city and explore independently.
Depending on how far outside the city (and suburb) limits you want to go, the following list of destinations has something to offer everyone, whether you want to spend the day just hours outside the downtown Loop or on the open road for a three-hour adventure into Illinois. So hop in the car, load your destination in one of the best GPS apps available and hit the road.
1. Gurnee, Illinois
50-minute drive from Chicago
The vibrant village of Gurnee may feel like a suburb of Chicago, but a brisk 50-minute drive north of the city will bring you to this wonderful location with something for everyone. One of the highlights of a visit to Gurnee is a trip to Six Flags Great America. If you love shopping more than roller coasters, consider a trip to Gurnee Mills, the city’s massive outlet mall. Seeking outdoor adventure? Consider one of the town’s many beautiful parks and outdoor spaces, including the Gurnee Park District.
If you’re in the mood for the perfect blend of small-town charm, urban amenities and plenty of things to do, visit Gurnee for the day or weekend.
2. Indiana Dunes, Indiana
1 hour drive from Chicago
With more than 2,000 acres of sand and shore, this is a great escape from the city to get outside and enjoy the day. Since being established in 1925, the Indiana Dunes State Park has provided visitors with easy access to 70 miles of hiking and 15 miles of swimming along Lake Michigan’s coast. If you enjoy bird watching, there’s more than 350 bird species flying around the dunes to admire. It’s a quick trip — just an hour’s drive from the city — that is sure to impress with its scenic views, challenging sand dune climbs and plenty of coastline for boating, fishing or laying out to soak up the sun.
3. Grand Beach, Michigan
1 hour, 20-minute drive from Chicago
Drive along I-90 E and I-94 E for just under an hour and 20 minutes to reach the village of Grand Beach, Michigan. This quiet locale offers a tranquil getaway for visitors, with sandy beaches, stunning lake views and quaint shops and restaurants. Compared to other locations on our list, Grand Beach’s amenities might seem lacking. But there’s a certain kind of charm in the quiet life. Golfers and beachgoers alike will appreciate the slow pace.
As part of the Harbor Country region, Grand Beach is within short driving distance of countless restaurants, ranging from fine dining to simple bar food and nearly everything in between. You can also experience the joy of visiting the area’s museums, botanic gardens and numerous parks.
4. Lake Geneva, Wisconsin
1 hour, 30 minute drive from Chicago
Who doesn’t love a day on the lake? Whether you’re looking for a relaxing getaway on the shore or a full day on the water, Lake Geneva has options for everyone. That’s what makes it among the best road trips from Chicago, with many Instagrammable views, good eats and endless activities, from boat rentals to zip lining.
5. South Bend, Indiana
1 hour, 40-minute drive from Chicago
Just under two hours from Chicago, South Bend is most known for being the home of the University of Notre Dame. While college football may make it a regular Saturday destination for many during the fall, that’s far from the only reason to visit this northern Indiana city. Other must-see attractions include the Potawatomi Zoo, the Studebaker National Museum and its vintage car collection, and the Basilica of the Sacred Heart, an architectural gem on Notre Dame’s campus.
Outdoor enthusiasts wanting a place to relax or adventure should head to the East Race Waterway and Rum Village Park. At the same time, foodies and beer fans will enjoy excellent local cuisine and breweries.
6. Starved Rock State Park, Illinois
1 hour, 40 minute drive from Chicago
This state park is free to enter and attracts millions of visitors each year. Pre-register to join a free guided hike from June to November, or go on your own and enjoy 13 miles of well-marked trails that pass by waterfalls and 18 canyons that offer amazing views of the Illinois River.
7. Rockford, Illinois
1 hour, 40-minute drive from Chicago
As with many destinations on our list, Rockford, Illinois, is a vibrant city with plenty to see and do. Visitors have great options for outdoor activities along the Rock River, including boating, fishing and kayaking. For those who want to stick closer to the shore, there are plenty of parks and trails to explore.
The outdoors isn’t the only thing to see in this town. Art lovers might visit the Anderson Japanese Gardens and enjoy beautiful landscaping and culture. History buffs should pay a visit to the Midway Village Museum. For those who want to sample the vibrant nightlife, consider visiting one of the city’s top-notch restaurants or whiskey bars before catching a concert or show at the nearby BMO Center.
8. Grand Junction, Michigan
2-hour drive from Chicago
If you’re seeking a fantastic destination for a peaceful getaway, Grand Junction is just a two-hour drive. This scenic locale has plenty to offer visitors. Visit the Stokes Homestead Farm Market in the fall, where you can pick your own fruits and vegetables and shop for homemade goods. Horse lovers should check out the Simpsarosa Stables and go horseback riding along scenic trails. If you’re more of a kayak or canoe person, the Paw Paw River is an excellent place to embark on an adventure. You can also visit nearby South Haven for a day along the Lake Michigan shoreline.
Grand Junction’s natural beauty and friendly atmosphere make this short trip well worth it, whether you plan to stay for one day or longer.
9. Cedarburg, Wisconsin
2-hour drive from Chicago
Cedarburg, Wisconsin, just north of Milwaukee, offers visitors the chance to escape to a quiet, charming town that boasts historic buildings and nostalgic appeal. One of the top attractions in the city, the Cedarburg Covered Bridge, provides the perfect backdrop for a romantic late autumn stroll. For the outdoor enthusiast, the Ozaukee Interurban Trail winds through the city and offers plenty of opportunities for walkers, joggers and bikers.
For those who love wine, the Cedar Creek Winery allows visitors to indulge in wine tastings among the beautiful vineyard surroundings. Finally, the historic district enchants visitors with opportunities for shopping and dining.
10. Elkhart Lake, Wisconsin
2 hour, 30-minute drive from Chicago
Making the two-and-a-half-hour drive from Chicago to Elkhart Lake, Wisconsin, means enjoying plenty to see and do in the great outdoors. The nearby Kettle Moraine State Forest is perfect for hiking and camping, and the lake is ideal for everything from water skiing and fishing to leisurely pontoon cruises.
For those who aren’t as outdoor-inclined, you can watch a race at the Road America race track or enjoy art at the Two Fish Gallery and Sculpture Garden. There’s also a large number of excellent places to grab a bite to eat or something to drink in the city’s bustling fine dining and craft brewery scenes.
11. Madison, Wisconsin
2 hour, 30 minute drive from Chicago
We’re neutral in the debate, but some say that Wisconsin’s best cheese curds can be found in Madison. Not just one restaurant in particular, but all around. If you’re up for the taste-test challenge, make your way around the city noshing on squeaky delights. Cheese aside, there’s plenty to enjoy about a visit to the state capitol, from free museums to lake and greenspace activities galore to fairs and festivals throughout the year. If your visit falls on a game day at the University of Wisconsin–Madison, go cheer on the Badgers!
12. Galena, Illinois
3-hour drive from Chicago
Galena, Illinois, is just shy of three hours from Chicago and offers visitors plenty of things to do. This lovely little burg is known for its historic charm, vibrant downtown and scenic beauty.
Explore the great outdoors along the Mississippi River or the beautiful Horseshoe Mound Preserve. History buffs might take a trip to visit the Galena-Jo Daviess County Historical Society, where you can learn about the town’s rich heritage. The Old Market House is another notable attraction that exhibits unique architecture.
Discover the best short road trips from Chicago
Taking a day or weekend trip out of the city can be an excellent way to reduce stress and see more of the country, but it’s not always easy if you don’t have a car. Luckily, Avail makes it simple to hit the road from our convenient neighborhood locations around Chicago.
Avail lets you borrow a vehicle from Chicago-area car owners with reasonable rental requirements and no fees if you’re under 25. We give drivers a generous daily distance limit of 200 miles, which is all you’ll need to reach the destinations on this list during a weekend trip.
If you’re looking for a convenient, easy way to reserve a vehicle for your short road trip, Avail can help. Browse available car rentals in Chicago and start your journey today.