Day Trips from Chicago

Chicago is a destination in its own right. You can easily spend weeks here and barely scratch the surface of what there is to do. Still, if you live here or tire of the city’s bustle, Chicago’s proximity to other places is unmatched. Day trips from Chicago are a piece of cake in any direction (except directly into Lake Michigan). 

In a matter of a few hours, you can be transported back in time, into the wilderness, or even to a lakeside resort destination. These are just a handful of options within three driving hours of Chicago, but the possibilities are practically endless. 

Starved Rock State Park, Oglesby, IL

• Drive Time from Chicago: 75 Minutes

You’ll feel worlds away at Starved Rock State Park, just over an hour outside the city. This gorgeous recreational area is known for its towering canyons and waterfalls, giving a glimpse into the region’s ancient past. Its macabre name stems from legend of a battle of vengeance between the Potawatomi and Ottawa against a group of Illinois. The Potawatomi and Ottawa kept the Illinois surrounded on the land, unable to flee, until the band of Illinois died of starvation – hence the name Starved Rock. 

Activities here range from boating and fishing to kayaking and camping. There are 13 miles of hiking trails to explore and even picnicking areas to enjoy. Plus, Starved Rock is dog-friendly, a fact my pup thoroughly enjoyed. Keep in mind that Starved Rock is relatively isolated, so be sure to bring any provisions you might need (and a first aid kit if you’re clumsy like I am). Admission to the park is free.

If you need a bite or want to stay nearby, I highly recommend Starved Rock Lodge. Parts of the lodge are a bit dated, though it fits with the rustic nature of the area, and it’s comfortable enough anyway. A restaurant and cafe are also on-site, which is a bonus. Since it is a boutique hotel it does book out quickly, particularly during the outdoor wedding season.

Lake Geneva, WI

• Drive Time from Chicago: 75 Minutes

To me, the best Chicago day trips are under 90 minutes and get you back to the city well before or after rush hour. That’s why the small resort city of Lake Geneva is perfect for a day’s adventure or even an overnight or two away from the city. Although the Midwest doesn’t have The Hamptons, Lake Geneva comes close to that level of luxurious comfort. 

Wealthy folks clamored for the lakeside shores of Lake Geneva in the 1800s, resulting in a swath of incredible mansions. If you’re familiar with Chicago architecture, think of posh homes like our Gold Coast. One of those homes has become a museum that you need to check out called the Black Point Estate and Gardens. You could even stay at one at the Maxwell Mansion Hotel! 

Elsewhere in the city, you can enjoy a blissful beach day, sip a local brew at the Topsy Turvy Brewery, or learn more about the area at the fantastical Geneva Lake Museum. As a born-and-raised Wisconsinite, I also recommend trying cheese curds while you’re here. Fried or fresh, they’re the best.

Galena, IL

• Drive Time from Chicago: 3 Hours

For history buffs, attractions outside Chicago can be less enticing. That is, of course, you’re talking about Galena. Although it’s a trek from the city, Galena is full of historic goodies and a stunning collection of buildings dating back to the 1800s. Galena is the place to be if you want a real taste of Midwestern life as it was two hundred years ago. 

Strolling down the main street is enough to satisfy even a shopaholic, but that doesn’t even consider all the museums! Pop into the Dowling House, built in 1826, or take a sightseeing tour aboard one of the Galena Trolleys. You can finish the day with a dinner at the Log Cabin Steakhouse and rest your eyes at the Chestnut Mountain Resort — a perfect stopover for winter day trips from Chicago. 

Indiana Dunes National Park, Porter, IN

• Drive Time from Chicago: 50 Minutes

Ranking fourth in biodiversity among all national parks in the United States, Indiana Dunes is an incredible place to see. That’s particularly true for birders and plant lovers since much of the biodiversity encapsulates those categories. Indiana Dunes is a terrific option for day trips from Chicago for families, especially if your crew is outdoorsy. There are 50 miles of hiking trails here, after all. 

A few of the activities you can do here include camping, fishing, horseback riding, picnicking, and boating, to name a few. Although the park itself is huge, it also runs across fifteen cities, giving visitors ample places to eat, rest, and enjoy themselves. Entrance fees vary based on vehicle and person, starting at $15. 

Madison, WI

• Drive Time from Chicago: 2.5 Hours

Last but never least is my beloved Madison. I lived there for several years and fell in love with this beautiful city, its art, and (of course) its food. I have yet to find a place that makes fried cheese curds or a Wisconsin old fashioned better than The Old Fashioned right by the Wisconsin State Capitol building. 

Beer lovers love Madison and Wisconsin in general for the vast array of local breweries. Namely, New Glarus beers, which aren’t sold out of the state. It’s common for folks to drive up for day trips from Chicago, Illinois, just to buy cases of Spotted Cow beer. While I’m not one of those folks, Madison is forever one of my favorite places to come back to. 

When considering where to stay in Chicago, plan out your basic trip itinerary. If that plan includes places to visit around Chicago, try choosing hotels on a side of the city that will make you closer to your day trip destinations. For instance, if you want to see Wisconsin, staying on the North Side makes more sense than the South Side because it’s closer and vice versa for Indiana. 

As much as I adore Chicago and exploring the Windy City, getting out is also an adventure. My favorite part of traveling is trying new foods, seeing new sights, and meeting different kinds of people. When it comes to endorsing all the Midwestern adventures, you’ll be hard-pressed to find bigger cheerleaders than myself. We don’t say “the Midwest is best” for no reason. 

Read more:

• 15 Exciting Things to Do in Chicago
• 11 of the Best Boat Tours in Chicago
• Exploring the Windy City: A Two-Day Itinerary in Chicago
• Chicago After Dark: Places To Visit in Chicago at Night
• When is the Best Time to Travel to Chicago

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