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Summer in the City: Chicago

Summer has finally arrived, and it will be my first working in Chicago. So, free from school and only working 50 hours a week, I am making it my mission to experience the city (hopefully without spending my whole stipend). This is my comprehensive list of things to do this summer in Chicago.

I reached out to everyone from colleagues at work to my sorority to make sure I don’t miss anything central to a Chicago summer. Then I organized it by price-level to make it easy for you to find the things in your price range. As always, let me know on Facebook or Instagram what I missed!

“U-Passes will be Deactivated over the Summer”

I’d call this section free, but since U-Passes don’t work over the summer, you just need a filled Ventra card to get you to fun.

Nearly everyone I spoke to mentioned the Millennium Park Summer Music Series, which are free concerts every Monday and Thursday at 6:30 PM (which gives you just enough time to get home from work, change into shorts, grab some snacks, and head downtown).

There are tons of outdoor exercise activities hosted by the Chicago Park District. Catch Yoga in the Park or Zumba classes around Chicago. The Park District also puts on Movies in the Parks, a series of outdoor movies with everything from La La Land to Captain America in parks across Chicago. I’m going to try to make it to National Treasure in Wicker Park.

My personal favorite Chicago Parks District event is SummerDance, free events in Grant Park where you can learn a new dance and then get two hours with either a live band or a DJ. I’d recommend bringing a partner or a big group of friends because it’s more fun making a fool of yourselves together.

Navy Pier has fireworks on Wednesdays and Saturdays all summer, so grab a blanket and find a rooftop parking lot to watch them on (Navy Pier itself is always packed and crazy expensive).

The best thing about the summer is the sunrise, and it comes extra early so if you’re still out from the night before or an early riser like me, its worth it.

Instead of Going to Chipotle

These are moderately priced activities that probably will cost you as much as it’ll take for you to hit that delivery minimum.

The Parks District is the real MVP of the summer. As a part of Night Out in the Parks, they have a number of cool evening activities. Several people I spoke to recommended Theater on the Lake, a theater festival put on by various theater companies around Chicago. I’m going to try to make Romeo y Julieta, an all Spanish production of the Shakespeare play running at Berger Park Cultural Center at the end July and beginning of August. Old Town School of Folk Music also has a bunch of concerts and dance events that might be worth checking out.

I’d also recommend checking out any of the great farmer’s markets around the city. Green City Market is popular and super instagrammable, but most neighborhoods have one. Maxwell Street Market has really good tacos. Logan Square, French Market, and Glenwood Park Farmer’s Market were also mentioned to me as must sees.

There are so many great places to eat, but since its summer, a few ice cream places my friends said were worth checking out are Sugar Shack (funnel cake sundaes), Mario’s Italian Lemonade (a Chicago staple, according to my friends), Margie’s Candies, Black Dog, Jeni’s (of course), Scooters (custard, not ice cream), Razpachos Neveria (they also make Dorilocos), and La Michuacana. Over the last two years, I have been on a one woman quest to find the best ice cream in Chicago, so I am excited to add these to my list of places to try.

Like an Uber to O’Hare, but Way More Fun

These are more expensive options, but are amazing experiences perfect for your weekend.

There are a number of amazing festivals around the city through the summer, but Taste of Chicago is supposed to be next level amazing. Bring lots of cash though, because some vendors don’t take credit cards and you won’t be able to keep yourself from splurging on these goodies.

For one of my friends, going to a Cubs game at Wrigley Field is a summer tradition. However, White Sox tickets are cheaper (and if your heart is at Fenway, then it really doesn’t matter which team you watch).

One of the best things you can do is to get out of the city for the day. Take the Metra either to St. Joseph’s or the Indiana Dunes. If you’re looking for something a little closer, Evanston has a lot of cute restaurants and might be worth the trip north.


God Bless you if you got tickets. Lmk if you want to sell them for like $20.


That’s my game plan for this summer, and I’d love to hear yours!

What did I miss? What shouldn’t I go to?

Tell me on Instagram or Facebook.


Xoxo, Rosana

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