The Best Things To Do In The Summer In Chicago

Thomas and I were lucky to have moved to Chicago in April because we knew our first few months in the Windy City were going to be sunny and warm unlike the rest of the year.  Summer in Chicago is a really big deal – people are out and about and embrace the warm weather. Between settling in and traveling, we have found some moments to also enjoy what Chicago has to offer during these months and here’s a list I put together for you all. Keep in mind that the longer we live here, the more I will learn so we will constantly be updating this list and all things “Chicago”!  Happy travels!

Chicago Festivals | Events, Food & Culture

I have a not so big secret for you…Chicagoans get very excited for everything Summer and with such brutal winters, who can blame them?! This also means that people here really take advantage of the Summer months by doing as much as they can outdoors. Chicago has a festival for EVERYTHING.  Since we’ve lived here there has practically been a festival every weekend! There’s something for everyone -whether you’re interested in food, music, or art – check out the schedule and pick a few to go to.

Rooftop Cocktails

Well, this is an obvious one! Chicago has some great rooftops – some of our favorites are ZED451, Soho House (members only), Cindy’s, London House Chicago, Cabana Club rooftop at The Robey Hotel.

Visit Skydeck Chicago

This is a MUST. If views are your “thing” (why wouldn’t they be haha) then add Skydeck to your summer must do.  The views of Chicago don’t get any better than this. Period. If you’re in the mood for a thrill, try the Ledge experience – not for the faint of heart but so awesome. The Ledge is a glass balcony extending four feet outside the 103rd floor of Willis Tower – perfect for that Instagram shot. I advise you to visit early in the morning as it does get busy and you’ll want to have enough time to see the exhibits and really take the time to take in the views.

Chicago River Boat Rides

We’ve done the architecture boat tour several times because this city was made for it. I can’t recommend it enough – this is a great way to spend the day on the water while learning all the history of this beautiful city! We usually choose the Seadog for the tour because it’s smaller and feels more personal. 🙂

Summer Picnic

Is there anything better than having a Summer picnic with those you love? Grab your blanket and basket and head over to watch a movie at Jay Pritzker Pavillion, Millennium Park and if you are in the mood for something more intimate and romantic, check out the Art Institute Of Chicago South Garden.

Roam the streets and get lost

Get out your car and walk the parks, and the different neighborhoods. The Summer is the one time you can walk Chicago since it’s way too cold to even think of taking long strolls. Thomas and I love to walk and this pretty much goes for wherever we travel to because if there’s one thing I know is that walking leads to those little gems along the way that make for memorable moments.

Beach it

Chicago is lucky to be surrounded by water – 26 miles of shoreline to be exact.  So pack that beach bag and spend the weekends sunbathing – I recommend checking out Montrose beach, Fargo, and Oak Street.


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