5 Easy Day Trips You Can Take From Chicago, My Favorite Included

I spent the entirety of my 20s living in the Windy City without owning a car. However, every so often, I’d get an itch to take a break from my beloved concrete jungle. I’ve curated a list of five easy day trips you can take from Chicago that are either located off the train lines or worth finding a buddy with a car.

1. Oak Park: Beloved by Frank Lloyd Wright

• Distance from Chicago: Approximately 10 miles

Famous architect Frank Lloyd Wright lived in Oak Park for 20 years. A quick jump on Chicago’s famous “L” will have you there in no time. Spend the day visiting the Frank Lloyd Wright Home & Studio and the Prairie School of Architecture Historic District. Once you’ve got your fill of history, head to the town’s adorable downtown area to fill your bag with goodies from local boutiques. Be sure to grab a meal at one of the many fantastic restaurants.

2. Galena: Home of Ulysses S. Grant

• Distance from Chicago: Approximately 165 miles

Historic Galena is easily one of the most charming towns in Illinois. Tour the former home of President Ulysses S. Grant, or enjoy a liquid treat at Galena Cellars Winery. Spend an afternoon wandering around the town’s cobblestone streets. You may even encounter a Civil War reenactment or two.

3. Starved Rock State Park: Your Outdoor Adventure

• Distance from Chicago: Approximately 95 miles

In a particularly flat state like Illinois, finding interesting hikes can be a challenge. Luckily, Starved Rock State Park offers 13 miles of hiking trails to explore. Complete with waterfalls, canyons, and lakes, the park offers a retreat into nature. Be sure to grab a meal with a view overlooking the park at Veranda (located within Starved Rock Lodge) on a sunny day. The casual restaurant often offers live entertainment.

4. Naperville: A Substitute for the Mag Mile

• Distance from Chicago: Approximately 30 miles

Year after year, Naperville has won numerous awards, solidifying its position as one of the best places to live in America. With its scenic riverwalk and bustling business district, it’s easy to see why. Located off the Burlington Northern Santa Fe (BNSF) train line, most train rides take an hour from Chicago Union Station. 

A staple summertime activity includes a visit to Centennial Beach. The former quarry is now a six-acre aquatic playground complete with swimming pools, diving boards, and a sandy beach. If getting your toes wet isn’t your thing, the Naperville Riverwalk is an excellent alternative. You’ll see everything from boutique shops to covered bridges. 

5. White Pines Forest State Park: Enjoy a Show

• Distance from Chicago: Approximately 110 miles

I’ve found that hardly any Chicagoans know about White Pines Forest State Park. However, I’ve been pitching a tent at this 100-plus-site campground for nearly 30 years. The 385-acre park boasts hiking trails, picnic spots, and plenty of streams in which to cast a line.

A highlight is White Pines Lodge. In addition to rustic cabin accommodations, the lodge frequently presents a ticketed dinner theater. Yes, Chicago has an illustrious performing arts scene. Yet, this small town’s local theater charms.

Chicago may be a world-class destination, but that shouldn’t stop you from venturing out to the rest of Illinois. These five easy day trips from Chicago are worth the commute for a lifetime of memories. Do you have any other day trip ideas you'd like to share? Please tell us about them!