Chicago Summer Things To Do

It’s not exactly where I’m from but it’s close enough: Chicago! Birthplace of 16 inch softball, skyscrapers, deep dish pizza and the backwards flowing Chicago River?? I always forget about that one.

However brutal it can be in the winter, Chicago in the summer is a shockingly clean city, filled with rich history, unique architecture, food, a plethora of outdoor events and great public transportation to get help you get around. If you’re spending any time in Chicago this summer here are some fun things to do.

Take A LSD Trip

Lake Shore Drive silly! Drive along Lake Michigan as you enter the Windy City. Adjacent to the road, you can also bike, walk or rollerblade down the Lakefront Trail.

If you’ve never been to Chicago, driving LSD or walking the Lakefront Trail are superb ways to visit some of Chicago’s famous landmarks like Navy Pier, North Avenue Beach, The Adler Planetarium, The Field Museum, Grant Park, Millennium Park (the place with the bean), Solider Field if there’s any bears fans left out there and more.

Ride The River

Chicago’s First Lady (the boat) offers a 90 minute sight seeing architectural tour filled with interesting historical facts, unobstructed (minus Sarah & Brian’s cameo haha) views of the city and best of all drinks onboard!

It’s a spectacular way to see the city, learn her history and who doesn’t enjoy a day on the water?! I highly encourage visitors and locals to take the ride!

Play On The Lake

For those that have more time (and Moo-La) can take it a step further and rent a boat! Create a flotilla at Chicago’s favorite party spot, The Play Pen. Looking to catch your dinner? Book a fishing charter out on the water. Want to work for your view? Rent a paddle board or kayak.

Chicago can also be enjoyed from the sand. North Avenue, Fullerton and Oak Street are just a few of the 24 sand beaches the city has to offer.

Get Festive!

Every single weekend in the summer the greater Chicagoland area is host to fairs, carnivals, festivals and concerts including Lollapalooza, the Air & Water show and the Windy City Smoke Out. Check out a small preview down below or check out the full list here.

• Square Roots Festival July 7-9
• Chicago Craft Beer Fest July 14-16
• Pitchfork Music Festival July 21-23
• Illinois State Fair August 10-20
• Chicago Jazz Festival Aug 31-Sept 3

Tourist Traps

Of course you can visit the famous Willis (previously known as Sears) Tower and test your courage on The Ledge. It is pretty cool and a great photo opportunity, however you only get a minute to actually be on the ledge due to the large crowds of visitors. That was my experience from years ago, now they offer timed ticket entry for $42, so maybe it’s changed. Let me know in the comments if so!

Hot take but, I don’t recommend Navy Pier. Every time I visit it feels only like a great place for kids, families and tacky shopping. Though, they do offer firework shows Wednesdays and Saturdays from Memorial Day to Labor Day and have a beer garden so maybe not all bad.

On the other hand, “The Bean” or properly known as Cloud Gate is a lively place for pictures, free and lives right around various other attractions. Therefore, certified fresh, should definitely visit.

Be Entertained

This summer the productions of MJ: the musical, Cabernet Zazou, Hades Town and To Kill A Mockingbird are coming to Broadway in Chicago. Attending performances are a fantastic way to support local artists and have a great night out with friends, family or colleagues.

Or have your night take a comical turn and visit any of Chicago’s famous comedy clubs. Places like Zanies, Second City and The Laugh Factory offer new comics nearly every night.

Things For Free!

Another amazing opportunity visitors and locals are offered during the summer are free outdoor movies at Millennium Park! Upcoming shows include Top Gun: Maverick, Black Panther, Clueless and more every Tuesday starting July 11th at 6:30.

Can’t make Tuesdays? Movies in the Parks also is returning this summer with even more movies throughout the week at various locations to make it convenient for all.

Before the movie you can even bust out a free outdoor workout with Strength In The City outdoor fitness classes or an outdoor yoga session with Fitness Formula Clubs.

Go To Museums

Whether you’re interested in science, the solar system, art or history, the city can provide. I personally recommend the Adler Planetarium and the Science and Industry Museum due to their vast coverage of unique exhibits like the Sky Show and this summer’s German U-505 Submarine Exhibit. But the city also is home to the Art Institute of Chicago, Field Museum, Holocaust Museum and plenty more listed here.

Looking for a reason to go that’s not rain? These are the days the museums are free. Disclaimer: some of them are only free for Illinois residents.

Visit & Find Out More!

All in all, Chicago is a magical place with a lot to offer in the summer. Whether you’re there for a weekend or the whole year, I hope you can check out everything it has to offer and all the rest I didn’t even get to touch on! As always do your own research before checking it out and let me what else there is to do in the comments!