Spending summer in the windy city? Lucky you! There’s so much to see and do in Chicago in the summer, and the weather is perfect for some city adventure and sightseeing.

Here’s our pick of the events and activities you just can’t miss…

Hike through the city

Chicago has its own answer to New York’s High Line – the 606, which is actually twice the length. This former elevated railroad has been converted into an area of green space that you can hike or cycle along, which stretches out for 2.7 miles. When the suns out, it’s the perfect time to go. You’ll pass through Logan Square, Humboldt Park, and West Town on your journey, with the city’s best restaurants and bars to duck into en route.

The Big Loop – Red Route, Stop: Hard Rock Café

Catch an outdoor concert 

The city is home to over 580 parks, so when the weather hots up, you just have to get out and enjoy them. Lincoln Park and Grant Park are the most popular with visitors, and the perfect place for a picnic. But, if you head to Millennium Park, you can catch a free concert on Mondays and Thursdays throughout summer as part of their Summer Music Series. The line-up features indie and jazz artists including up-and-coming indie rockers, Whitney, and Jamaican reggae troupe The Kingston All-Stars.

The Big Loop – Red Route, Stop: Millennuim Park & Palmer House Hilton

Fly over the skyscrapers

Chicago is the setting for so many superhero movies, thanks to its cinematic urban landscape and soaring skyscrapers. Take to the skies, like Batman and co, and you’ll see exactly why. Summer is the perfect time to experience the city from up above and treat yourself to a Chicago Helicopter Experience. The 15-minute flight will take you soaring over the city skyline spotting iconic landmarks like the Willis Tower, Magnificent Mile, the Tribune Tower and Wrigley Field. Your pilot will provide an informative commentary and top sightseeing tips as you enjoy the view and take endless snaps.

Chicago Helicopter Experience Tickets

Head to the beach

One of the best things about a break in Chicago is being able to enjoy city sightseeing and beach time in one holiday. North Avenue Beach and Oak Street Beach are the most popular summer spots. You can enjoy sunbathing, sandcastle-building and volleyball games here, all with a backdrop of the city skyline. There’s also Ohio Street Beach which is the perfect spot for a swim and Helen Doria Beach which is more of an uncrowded, secluded spot.

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Enjoy the firework shows

You don’t have to wait until the Fourth of July for a fireworks show in Chicago. During summer, there’s a free fireworks show on Navy Pier every Wednesday and Saturday. You’ll get a good view from anywhere along the pier, so grab a beach blanket and settle down for the display. Or, head to one of the nearby rooftop bars for an elevated view.

The Big Loop – Red Route, Stop: Navy Pier

Dance the day away

Dance classes might not be your usual city break activity, but these classes are absolutely free and right in the middle of Grant Park. Chicago Summer Dance put on lessons almost every day over summer where you can learn everything from swing and ballroom to salsa and line dancing. There’s even bhangra, Bollywood dancing and bachata on the schedule. Once you’ve learnt the moves, you can dance along to the live bands who play sets during the event, too.

The Big Loop – Red Route, Stop: The Chicago Hilton & Grant Park
Chicago Summer Dance

We’ve only just scratched the surface of all the things to do this summer in Chicago. Stroll around the city and you’ll discover plenty more. And, if you need more inspiration for your trip, browse our Chicago bus tours.