8 Short Road Trips from Chicago Under 100 Miles

Chicago is a city that is full of great art, architecture, food and has many things to do for residents and tourists alike. It also has a great public transportation system, is walkable, and is very bikeable, increasing the ways to get around the city. Whether you’re visiting the Windy City for a few days or live there and are looking for a little adventure, you might be considering weekend getaways from Chicago. We’ve rounded up eight short road trips from Chicago that are under 100 miles away.

1. Indiana Dunes National Park, Indiana 

8 Weekend Getaways from Chicago Under 100 Miles | Metromile

If you’re looking for a Chicago getaway that is close by and want to enjoy a natural habitat, consider heading to Indiana Dunes National Park. According to IndianaDunes.com, the locale is home to a whopping 15,000 acres, 350 types of birds, and more than a thousand flowering plants. 

You also get to explore 15 miles of the shoreline and can take advantage of 50 miles of trails. You can go hiking or horseback riding on Glenwood Dunes Trail, relax at Dunbar Beach, and grab a bite at Aaron’s Mortgage Inn. Find more information about Indiana Dunes National Park here. 

Distance from Chicago: 36.2 miles 

How long it takes to get there one-way: 44 minutes 

2. Elgin, Illinois 

Elgin Illinois

Another short Chicago getaway option is to Elgin, located in Northern Illinois as part of the Fox River Valley. You can hike and bike at the Jon J. Duerr Forest Preserve or explore the Fox River Trolley Museum. You can also see a show at the Hemmens Cultural Center, which is located along the Riverwalk. Grab some pizza at Riverside Pizza and Pub or grab some espresso or a cocktail at Mockingbird Bar + Garden. Find out more information about Elgin here. 

Distance from Chicago: 40.5 miles 

How long it takes to get there one-way: 48 minutes 

3. McHenry County, Illinois 

Mc Henry County

Looking for weekend getaways in Chicago during the winter months? Look no further than McHenry County. You can enjoy skiing, snowshoeing, sledding, ice fishing, and more. You can satisfy your sweet tooth at Julie Ann’s Frozen Custard and stay at a beautiful Victorian home at Cherry Tree Inn Bed and Breakfast. Find out more information about McHenry County here. 

Distance from Chicago: 62.8 miles 

How long it takes to get there one-way: 1 hr and 18 minutes 

4. Kenosha, Wisconsin 

Kenosha, Wisconsin

One of the top weekend getaways from Chicago is Kenosha, Wisconsin where you can enjoy the beauty and majesty of the Lake Michigan shoreline. You can enjoy the public art in the city, see the two signature lighthouses, and go by streetcar. 

You can explore the Dinosaur Discovery Museum or have a beach day at Alford Park and Beach or go skiing or snowshoeing in the winter. You can grab your morning coffee at Harborside Common Grounds or enjoy a beer and a bite at Kenosha Brewing Co. (fun fact: 90 years ago, monks in Kenosha mastered the art of creating beer in the same location). Find more information about Kenosha here. 

Distance from Chicago: 66.2 miles 

How long it takes to get there one-way: 1 hr and 13 minutes 

5. Harbor Country, Michigan 

Harbor Country

Can’t decide between a beach or forest getaway? Why not do both in Harbor Country, Michigan. Harbor Country is home to eight towns nestled along Lake Michigan. You can go to Warren Dunes State Park and enjoy hiking, various winter sports, and dunes along the beach. 

You can also enjoy the 105-acre Friendship Botanic Gardens which has trails and playgrounds for kids. Adults can enjoy wine tasting (just be sure to avoid driving to avoid a DUI) and dinner at Tabor Hill Winery and Restaurant and can stay at Baymont Inn and Suites. Find more information about Harbor Country here. 

Distance from Chicago: 72.9 miles 

How long it takes to get there one-way: 1 hr and 16 minutes 

6. Lake Geneva, Wisconsin

Lake Geneva Wi

A top destination for weekend getaways from Chicago is Lake Geneva in Wisconsin. You can ski and do winter sports at Wilmot Mountain or in the summer enjoy Riviera Beach. You can also go ziplining or get your dose of local history at the Geneva Lake Museum.  

If you’re a foodie and want to enjoy the surroundings, head to Frontier Restaurant at Lake Lawn Resort for dinner and stay the night there at Lake Lawn Resort. Find more information about Lake Geneva here. 

Distance from Chicago: 83 miles 

How long it takes to get there one-way: 1 hr and 29 minutes 

7. Rockford, Illinois 

Rockford Il

Ready for a Chicago getaway that is the size of a big city but feels like a small town? Then Rockford is your next destination. If you’re going with kids, check out the Discovery Center Museum. Are you an art lover? Check out Rockford Art Museum

You can also hike, bike, golf, ski, or bird watch at the expansive Forest Preserves of Winnebago County. Two must-visits for garden lovers include Anderson Japanese Gardens and ​​Nicholas Conservatory & Gardens. You can dine at Abreo and stay at a local hotel or go camping at a nearby campground. Find more information about Rockford here

Distance from Chicago: 88.9 miles 

How long it takes to get there one-way: 1 hr and 33 minutes 

8. Milwaukee, Wisconsin

Milwaukee WI

When it comes to road trips from Chicago, Milwaukee is another great destination. You can explore the Milwaukee Art Museum or Milwaukee Public Museum and take a stroll down the Riverwalk and explore local art and breweries. Grab some lunch and a pint at Lakefront Brewery and go golfing, to a casino, biking, and much more. Stay in downtown Milwaukee at ​​Dubbel Dutch. Find more information about Milwaukee here. 

Distance from Chicago: 92.1 miles 

How long it takes to get there one-way: 1 hr and 31 minutes 

The bottom line 

If you live in Chicago or are just visiting, you can enjoy these eight destinations if you’re looking for close road trips from Chicago. These options are good weekend getaways from Chicago that you can enjoy in a few days or even if you just want to take a day trip. While on the road, you want to make sure you’re covered and prepared. That can include having the right car insurance. Low-mileage drivers can benefit from pay-per-mile coverage and pay for miles based on how much they drive. Check out a free quote with Metromile and get roadside assistance to stay protected on your road trips. 

​​Melanie Lockert is a freelance writer, podcast host of the Mental Health and Wealth show, and author of Dear Debt. She’s a cat mom to two jazzy cats, Miles and Thelonious, an amateur boxer, music lover, and needs coffee to function.