20 Things Every True Chicagoan Should Do This Summer

It’s already the middle of the summer, and it’s been a hot one in the Windy City.

Listen up, don’t just rely on the AC in your house or hotel to ride out the days, there’s plenty of awesome things to do in the city that are worth venturing out for before summer comes to an end.

We came up with a list of 20 quintessential Chicago summer activities that would make any native Chicagoan proud. 

This list has a little of something for everybody, from family activities to the best places to booze and brunch.

Looking to woo that summer fling? Many of these can double as warm-weather date ideas.

Did we miss one of your favourite things to do in Chicago in the summer? Add it in the comments!

Dress in your best hipster gear and go party at Chicago's Lollapalooza in early August. This year's Grant Park fest will have tons of well-known headliners such as Mumford & Sons, The Killers, Imagine Dragons, and Ellie Goulding.

Cheer on the Cubs at the historic Wrigley Field. This year, you can try new food items like a chicken and waffle stick or a bison bratwurst. (You could also go to US Cellular Field if you're a White Sox fan.)

Explore Chicago's 50-acre playground, Navy Pier. Make sure to ride the Ferris wheel and take in views of Lake Michigan and the city.

Head over to North Avenue Beach and get your tan on. Then later, make your way over to Castaways for some good food, music, and a slushy, fruity drink.

Stroll through Jackson Park's peaceful Osaka Garden. It's a little hard to find (head south of the Museum of Science & Industry), but bring a book and relax by the water to feel completely rejuvenated. Plus, it's free!

Plan your own summer hot dog tour of Chicago, and see just how good a poppy seed bun, yellow mustard, white onions, relish, a pickle, tomato slices, and pickled sport peppers can be with your frankfurter. We recommend starting at Hot Doug's for some of the best in the city.

Spend a day ambling around Lincoln Park and check out the amazing Chicago Zoo for free. Make sure to also say hi to the sea lions at the Kovler Sea Lion Pool and watch them bolt through the water.

Gaze at the Buckingham fountain at night when it's all lit up. It's one of the biggest fountains in the world, so grab a seat on a nearby bench and watch the beautiful 20 minute light and water show.

Chow down and dance at the best street festival of the summer, Wicker Park Fest. In late July, it takes place over one jam-packed weekend with live music, vendors, and art performances. Plus, it's only $5.

Take in the Chicago skyline on a Shoreline Sightseeing tour. The company has been around since 1939 with guides who narrate interesting facts, background, and tidbits about the Windy City and its buildings. Bonus: Take the evening Fireworks Cruise to get a fantastic view.

Snag a table at Big Star outside and order some of the best tacos Chicago has to offer. The pork belly and al pastor tacos are insanely good in particular. Plus, the drinks there are always strong.

Sip on a cocktail while soaking in the city lights at a rooftop bar. One of the best is at J. Parker — the drinks are fantastic, but it's the iconic Chicago buildings and swanky atmosphere that make this scene truly spectacular.

Stake out a prime spot on the beach and catch Chicago's Air and Water show in mid-August. Daredevil pilots, parachute teams, boat jumping, and jets flying in formation will keep you on the edge of your seat.

Meander around the Alfred Caldwell Lily Pool, another one of Chicago's hidden gems. It's one of the most romantic places in the city, so don't be surprised if you see a couple get engaged during your visit.

Snap pictures at the Chicago Yachting Association's 54th annual Venetian Night at 31st Street Harbor. Lighted and decorated boats parade by revelers on Lake Michigan, competing for awards while live music plays in the background.

Get to a prime fireworks-viewing spot in Millennium park on Wednesdays and Saturdays during the summer to watch the Navy Pier fireworks over the city.

Run, walk, bike, or roller blade along Lake Shore Drive. The views in either direction — from Sheridan road down to the South Side — are fantastic, with boats and beach areas adding to the picturesque skyline.

And last but not least, it's not a trip to Chicago without a visit to the Shedd Aquarium. The largest indoor aquarium in the world with more than 8,000 aquatic animals, it's a great place to escape the summer heat and tap into your inner child.

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