When warm weather arrives in Chicago, tourists and locals alike head out to enjoy the endless number of Windy City activities and copious amounts of sunshine. We’ve partnered with Kirsten Maxwell of Kids Are A Trip to give us the inside scoop on the best things to do in Chicago in the summertime. 

1. Take a tour of the city

One of the best ways to get acquainted with the city is to take a tour. Try exploring on land with a Hop-On Hop-Off Bus Tour, segway tour, or something unique like a Bikes, Bites, and Brews Tour. Seeing the city from the lake or on the river is just as exciting. There’s a boat tour that will heads out on Lake Michigan and showcases the major attractions or a riverboat architecture tour that details the marvels of Chicago’s architecture along the Chicago river. Any of the Chicago tours make for a memorable introduction to the Windy City.

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The Chicago River has a great architectural tour.
Photo: @kidsareatrip

2. Hang out at the park

Millennium Park is the main attraction in the city for many reasons. During the summer the park hosts several festivals. At the park’s Jay Pritzker Pavilion, there is a weekly film and music series with outdoor films and concerts. It’s the perfect place for a picnic and a show. The park also features the famous Chicago “Bean” (real name Cloud Gate) and the Crown Fountains. Between Millennium Park and the lakefront is Maggie Daley Park, a 20-acre public park with a climbing wall, play garden, and skating ribbon (open in the winter). It’s a fantastic addition to the downtown landscape.

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Don’t miss The Bean!
Photo: @kidsareatrip

3. Go to a festival

Summer is festival season in Chicago and there are plenty to choose from. Some of the major ones are Lollapalooza, Taste of Chicago, Chicago Blues Festival, and the Pitchfork Music Festival. There seems to be a weekly festival is every neighborhood. Some of the favorites include: the Andersonville Midsommarfest, Pilsen Food Truck Festival, Rib Fest, Chinatown Summer Fair, and Taste of Greektown. There’s a festival on every weekend for everyone.

4. Grab a drink or dinner at a rooftop bar/restaurant

Chicagoans love dining al fresco and rooftop bars and restaurants are extremely popular in the summer. Cindy’s atop the Chicago Athletic Association is a perennial favorite place for a cocktail while taking in the views of Millennium Park and Lake Michigan across the way. London House Hotel has a killer location, with a rooftop overlooking the Chicago River and Michigan Avenue. Loews Streeterville Social has a lawn area with games like giant Jenga and bean bag toss. It is perfect for a fun cocktail with a city view.

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Loews Streeterville Social is a great summer gathering spot.
Photo: @kidsareatrip

5. See the fireworks over Navy Pier

Twice a week from Memorial Day to Labor Day, Navy Pier sets off fireworks over Lake Michigan. The ideal viewing spots for the performance are at the end of the pier, aboard a cruise ship on the lake, or aboard the Centennial Ferris Wheel at Navy Pier. If fireworks aren’t a priority, have a meal at one of the Navy Pier restaurants or catch a performance at the adjacent Chicago Shakespeare Theater for a fun night out.

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Don’t miss the view from the Centennial Wheel!
Photo: @kidsareatrip

6. Spend the day at the beach

Chicago boasts 26 miles of beautiful beaches along Lake Michigan, making the beach a perfect spot to spend the day. Pack the towels, sunscreen, and snacks or simply go for a walk. There are over two dozen beaches in the city, and locals and visitors love Chicago beaches and long days in the sun.

7. Explore the 606

The 606 was an abandoned rail line before it was revived a few years ago. It is a three-mile trail connecting four unique neighborhoods: Bucktown, Wicker Park, Logan Square and Humboldt Park. The main path is set above the city streets and is perfect for biking, running, and walking. The trail runs through six city parks and features urban art installations along the way. On the western end of the trail is an observatory with great sunset views and occasional astronomy viewings.

8. Visit world class museums

Chicago is home to world class museums, and while the sunshine might keep visitors outside, it would be a shame to miss these attractions. The Art Institute of Chicago is worth at least a few hours of time to see famous works such as: Van Gogh’s Self-Portrait, Renoir’s Two Sisters, and Hopper’s Nighthawks. Other worthwhile museums include the Museum of Science and Industry, the Chicago History Museum, the National Museum of Mexican Art, and The Field Museum.

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Don’t miss Sue the T-Rex at The Field Museum.
Photo: @kidsareatrip

9. Head out to a ball game

No visit to Chicago would be complete without a visit to a ball game. Everyone wants to experience Wrigley Field, and now that the Cubs won the World Series, a ticket might be tough to find. Grab some friends, hop on the train, and head to Wrigleyville. There are plenty of places to grab a bite and a brew around the ballpark without tickets. Once you make your way in, grab a Chicago dog and a cold drink. If the Cubs aren’t your thing, head across town and see the White Sox play. Either way, it’s a perfect day in the city.

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Don’t miss a ball game!
Photo: @kidsareatrip

Kirsten Maxwell is an official Travelocity Gnational Gnomad. Gnational Gnomads is an exclusive group of high-profile travel and lifestyle experts who offer tips and inspiration on behalf of Travelocity. For more information on the Travelocity Gnational Gnomads, visit TravelocityGnomads.com.

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

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