Planning a day trip can be the perfect way to explore a region, spend time with loved ones, and make memories that will last a lifetime. Where better to experience enjoyment than the Windy City itself? One of the largest cities in the U.S., Chicago is known for its bold architecture, high-quality museums, and, of course, delicious deep-dish pizza. Whether you want to eat good food, do fun activities, explore nature, see amazing views, or learn about history, this place has something for you.

Beautiful natural landscape outside of Chicago area.
Image via Unsplash by darkersolstice using Unsplash License

Read on to discover some great ideas for day trips and activities you can do in or from Chicago, Illinois.

Chicago Botanic Garden

With a whopping 385 acres of gorgeous, landscaped gardens, and millions of plants and flowers to see, you’ll want to save a whole day to visit the Chicago Botanic Garden. There, you can find 27 different gardens and natural spaces to explore, including the English Walled Garden, the Prairie, the Japanese Garden, the Rose Garden, the Nature Reserve, and the Sensory Garden. In addition, there may be temporary shows and events happening, so be sure to check the website before your trip. For example, the springtime Orchid Show celebrates the diversity and vibrancy of wild orchids and tropical plants.

If you’re looking for a more unique experience, the Chicago Botanic Garden also offers classes and workshops on wellness, fitness, yoga, photography, gardening, cooking, and horticulture. On the website, you’ll find both in-person and online educational opportunities for adults and children. The garden also works on a variety of projects in the community, like the Farm on Ogden, a multi-use facility, indoor market, and urban agriculture program. By touring this facility, you could check out the 50,000-gallon aquaponics system and 7,300-square-foot greenhouse.


Naperville is a suburb in the west of Chicago, a 40-minute drive from downtown, with recreation, dining, museums, shopping, and entertainment that visitors of all ages can enjoy. One of the most popular attractions in the neighborhood is the Naperville Riverwalk, a 1.75-mile trail of brick paths, bridges, fountains, sculptures, memorials, and more. This beautiful nature walk is a wonderful place to stroll, relax, and appreciate the great outdoors. To absorb some Naperville history, explore the Century Walk, complete with murals, mosaics, sculptures, and artwork that represents the rich past of the city.

For an interactive experience, consider signing up for a class or workshop at the Naperville Fine Art Center and Gallery. You can also walk the grounds to study the current exhibitions and pieces from local emerging and established artists. Feeling hungry? A local restaurant in the city, Angeli’s, is sure to keep the entire group happy. This cozy trattoria and bar serve a variety of authentic Italian comfort food options. Of course, if you need some caffeine earlier in the day, be sure to check out Yogi’s Cafe, a local coffee shop serving lattes, tea, sweets, and other specialty drinks.

Wicker Park

Just an 11-minute drive from the city center, Wicker Park is a charming neighborhood enclave with plenty of dining and entertainment venues, vintage shops, and quirky cafes to explore. Start your day trip off with breakfast at Hash, a hearty breakfast and lunch eatery with ’70s rock-inspired decor. Then, have a walk along The 606, a multi-use recreational trail on an old rail line with art installations, murals, and green spaces. For a midday pick-me-up, stop at Fairgrounds Coffee and Tea for some craft drinks and seasonal snacks.

If you’re a book lover, Myopic Books could be an ideal stop on your Wicker Park tour. Along with a stock of over 80,000 stories, this tri-level used book store also hosts occasional concerts and poetry nights. There’s also a bounty of shopping opportunities in this area. Take a trip back in time by exploring Kokorokoko, an eccentric vintage clothing shop with pieces from the ’80s and ’90s. Later in the evening, you might visit Phyllis Musical Inn, a long-running dive bar and outdoor beer garden with live music and a casual, saloon environment.

Montrose Beach

What’s a more relaxing activity than sitting on the beach? About 20 minutes away from downtown Chicago, Montrose Beach is a public, seasonal beach in Cook County. Here, you can swim in the salt-free Lake Michigan water while enjoying a stunning view of the city skyline in the distance. Consider bringing supplies to grill burgers and hot dogs on the beach. You’ll also find amenities like food concessions, kayak and volleyball rentals, and on-site showers and restrooms. There are even designated dog-friendly areas of the beach. Lifeguards help you feel safe, especially when bringing children.

An ADA-accessible beach walk is available, on which you can watch for swamp birds and sailboats. There’s also a bicycle path available. A great outdoor restaurant, The Dock At Montrose Beach, offers classic American fare like grass-fed burgers, Great Lakes whitefish, and locally sourced produce. Along with cold beers, boozy cocktails, and Caribbean-inspired wines, you’ll also find live music throughout the summer. Don’t forget to hang out on the patio or walk along the beach to witness a romantic, colorful sunset. You might even visit the Hollywood Beach Pierhead Light nearby.

Oak Park

Art fans may be excited to visit Oak Park, a village about 20 minutes away from Chicago, to see the home and studio of Frank Lloyd Wright, a famous American architect, designer, and writer. This historic house and museum was the residence and workplace of Wright for the first twenty years of his career and the place he created the Prairie architecture style. By touring this property, you’ll find full furnishings and textiles, all originals designed by Wright. You can also find Wright designs throughout this and surrounding areas, including the Arthur Heurtley House and the Avery Coonley House.

The Oak Park Conservatory, free to the public, offers another great option for a day trip to the suburb. There, you can explore the Mediterranean, tropical, and desert indoor conservatory showrooms and a variety of urban outdoor gardens around the property. For a more interactive, family-friendly experience, you might try the Wonder Works Children’s Museum, a 6400 square-foot building with exhibits and educational programming for kids. Five “experience zones” and an outdoor organic garden will surely keep the family occupied.

As you can see, Chicago doesn’t have a shortage of exciting activities to do. What are some of your favorite day trips in or near the area? Did we miss any of the best spots? Let us know here at American Auto Insurance and we’ll add it to our list.


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