11 Things You Must Do This Summer in Chicago

11 Things You Must Do This Summer in Chicago

Nothin’ quite like summertime Chi… Here’s how to make the most of it.

As of yesterday, it’s finally summer here in the Northeast — officially so, at least. Happy Solstice, my friends! (Does anyone else watch Broad City? And if so, do you read that as sol-steece?)

chicago millenium park view from cindy's rootop bar

Summer and travel  — two things that essentially go hand-in-hand. There’s just something about longer days and hot, humid nights that have me longing for the chance to take a little vacation… (Or maybe it’s the fact that I don’t live in New York and can no longer escape to the Hamptons every weekend, but I digress.)

Luckily, Chicago is an incredible place to be in the summer. (I am still planning that weekend away, though — but we’ll get to that in a sec.)


Lots of you have asked for a handful of my local recommendations — and since summer is my favorite time of year to be in the Windy City, I thought it’d be fitting to share them with you given the official start of the season.

Even though I’ve lived here for nearly six years in total (five or so of them before I moved to New York for a while), there’s so many cute spots, events and activities that I haven’t yet had a chance to check out. So, if you have additional suggestions, please feel free to leave ’em in the comments.


Without further adieu — here’s a handful of my favorite things to do in Chicago every summer.

Go to a music festival. Whether it’s Pitchfork, Spring Awakening (#SAMF), Lollapalooza or a free concert in Millenium Park. I’m a total live music junkie — already counting down the days ’til each! There’s also a series of summer concerts at Millenium Park (for free) and Ravinia, which is a short train ride from the city.

… And a street festival. Taste of Randolph, Old Town Art Fair, Do Division Street, you name it. Chicago’s many, many street fests happen every weekend (seemingly) and they’re a great way to experience the food, drink and culture of different parts of town.

Play hooky and head to Wrigley for a Cubs’ game. Sit in the bleachers and indulge yourself in a Bud Light (or two). Yolo!

Cross off as many al fresco happy hour locations as you can. Pizza? Head to Happy Camper (Old Town) or Parlor (West Loop/Wicker Park). Tacos? Big Star (Wicker Park). Obviously, you can’t go wrong with the city’s many rooftops. Places I frequent include City Winery, Cindy’s Rooftop, Bar Sienna, Sheffield’s Beer Garden and all of the aforementioned. Next on my list are London House and Kaiser Tiger — two newer spots that opened up this season.

corals and cognacs chicago lifestyle blogger

Have an outdoor movie night in Millennium Park. Grab a blanket, your girls and BYOWACP (wine and cheese plate) for a movie night on the lawn at Jay Pritzker Pavilion in Millennium Park. This year’s Summer Film Series is every Tuesday — starting today — through Aug. 30 at 6:30 p.m. (FYI: Seating is first-come, first-serve.)

Run along the lakefront. Run, walk, rollerblade, whatever — you can also rent a Divy bike, too, to take your trip a bit further north. The view of the city alone is worth it. Get those sunset ‘grams!

Spend your Saturday at one of the city’s beaches. Oak Street is usually less crowded than North Avenue — plus, the views are better. (Or even better, find a friend who has a boat!)

best placse to take photos with chicago skyline in the background

Shop: Gingham picnic blanket


Take an architectural boat tour on the Chicago river. This is one of my favorite tourist activities to partake in — it’s so nice to sit back, relax and take in the history/every angle of the city’s skyline (and get a tan while you’re at it).

Explore Navy Pier. One of Chicago’s most famous landmarks recently celebrated it’s 100th birthday with a major upgrade/redevelopment plan. There’s live music, an iMax theatre, tons of food options and much more. Plus, the newly renovated Centennial Ferris Wheel is back. Go on a Wednesday or Saturday night when you can catch the fireworks (at 9:30 p.m.).

Get in on an intramural kickball, softball or volleyball game… If you’re a local. Or just meet your crew for that post-game happy hour. I’ve met so many cool people through Chicago’s pick-up sports leagues. (Hey, boys!)

Indulge yourself in a weekend getaway. Last but not least, make it a point to escape your reality for a quick retreat. At the top of my list this season is Nashville, Tennessee — I’ve been before, but only for a bachelorette party-oriented trip, so I feel like I didn’t really get to experience the best that the city has to offer. From what I remember, it’s a destination that embodies everything about that Southern hospitality. I haven’t always been a country-loving gal, but that’s changed as my sisters and I have gotten closer over the past few years. Plus, what’s not to love about live country music in the summer, right?

Have you been?

what to pack for a weekend trip

Shop: MZ Wallace quilted ‘Metro’ tote


Earlier this month, I was downtown near Grant Park when I caught a live-streamed concert sponsored by Tennessee’s Tourism Department. It spotlighted the talents of various Memphis, Nashville and Knoxville natives (including Citizen Cope, Jason Isabel, Old Crow and Ashley Monroe).

Admittedly, I didn’t know most of these artists, but my sister Lisa did — but the time we spent listening to the live stream-style show left me longing to take a trip to the global music destination, especially since it’s a short flight or quick drive from the Windy City. (You can click here to read more about Tennessee’s Tourism options.)


So, in sum: Eat, drink, spend time outdoors. And when you get the chance, escape your reality.

What are some of your favorite summer activities?


Thanks to TN Tourism for partnering on this post. All opinions are, of course, my own.

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