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Your Chicago Summer Bucket List

A top ten list for your summer in the city!

Downtown Chicago viewed from the river

Any good Chicagoan knows that Chicago earns its summer. We suffer through brutal winters, so when the summer arrives, we know how to celebrate it!

Whether you’re just stopping in for a Chicago summer, or whether you’re a native Chicagoan taking a seasonal victory lap, here are the things you absolutely must do in a Windy City Summer!

1 - Go to the Beach!

Chicago may not seem like a beach town, but if you think Chicago isn’t a beach town, you’ve clearly never visited in August! A beach day is an absolute must on a summer bucket list!

Lake Michigan in Chicago is dotted with amazing sand beaches, most of them surrounded by amazing family-friendly parks. My personal favorite, mostly by virtue of it being the closest to my house, is Loyola Beach. Foster Beach and Montrose Beach also get a lot of hype!

Lake Michigan never truly becomes warm, so if you want to swim, make sure you’ve picked a properly warm day. The water will be wonderfully refreshing and you can lay in the sun afterward to warm up.

a kayaker on the Chicago River

2 - Explore the Chicago River

And speaking of Chicago’s water features, there’s no better time to explore the Chicago River than in the summer. Book a boat tour and learn about the city’s architecture, or grab a spot on a kayak tour and explore the waterways on your own terms!

the Chicago Riverwalk at night

3 - Patio Dining

While you at the Riverwalk for your boating adventure, check another Chicago summer staple off your list at the same time: the patio dinner.

There are countless wonderful pubs and restaurants along the Riverwalk, most of them only open in the summer, and all of them with amazing riverside patios! You can find something for every taste, but my personal favorite is Northman on the Riverwalk, a cider bar and Bavarian food haven with river views and live music every weekend.

4 - Sample Some Amazing Ice Creams

Time for sweet treats! Take advantage of the hot weather and treat yourself to something delicious!

It’s hard to go wrong with ice cream in the summer, but I can personally recommend Jeni’s Ice Creams for unique flavors, and Lickity Split for candy store custard magic.

the bandshell in Grant Park, Chicago

5 - Picnic in Grant Park

Every summer, the Grant Park Music Festival hosts weekly classical music concerts at the Grant Park bandshell. Best of all, these concerts are completely free! Yes, you can purchase tickets for the seats nearest the stage, but the best way to experience Grant Park is with a picnic blanket on the lawn. You can bring in your own food and drink, including alcohol, so pack a picnic and go enjoy a classical concert on the lawn. It’s true Chicago summer magic.

6 - Visit Chicago's Free Zoo

Summer in Chicago is the perfect time to explore the Lincoln Park Zoo! This institution is an absolute masterclass in inner city zoo design, with tons of animals and attractions. And guess what else? Admission is free! There’s no reason not to spend an amazing summer afternoon at the Lincoln Park Zoo. Say hi to the lion cubs for me.

the Art Institute of Chicago with Lion Statues

7 - Beat the Heat in a Museum

Does all the summer heat have you scrambling for air conditioning? Beat the heat at one of Chicago’s amazing museums. Between the Field Museum of Natural History, the Shedd Aquarium, the Art Institute, or the Adler Planetarium, there’s something for everyone, and any of these are an awesome place to spend an afternoon when you need to get out of the sun!

8 - Visit a Festival

Summer is peak festival season in Chicago, with street festivals happening somewhere in the city most weekends. From Midsommerfest kicking off the summer in Andersonville every June, to food-focused festivals like Ribfest, to nationally known music festivals like Lollapalooza, there’s always something happening in Chicago.

Look up the schedule and see what catches your interest!

9 - Visit a Farmers Market

Summer is also farmers’ market season in Chicago, where local farmers and artisans gather to sell their produce and their wares. My home market is the Glenwood Sunday Market in Rogers Park, which serves up locally grown produce side by side with delicacies like artisan cheese, bakery treats, fresh eggs, and gourmet coffees.

a cosplayer at the Bristol Renaissance Faire

10 - Take a Trip Back in Time

If you’ve got a car and want to get out of the city and into the past, the Bristol Renaissance Faire is just a short drive away! If you’re a ren faire aficionado, Bristol is consistently voted among the best in the country, and will blow you away! If you’re unfamiliar with ren faires, Bristol will absolutely ruin you for other ren faires in the best possible way!

It’s miles of magic, consisting of amazing attractions, delicious food, unique shopping experiences, period-appropriate entertainment (up to and including live jousting!), and the best damn people watching you’ve ever experienced in your life! Don a costume and step back in time! It’ll be the time of your life. It’s open on Saturdays and Sundays from July to Labor Day.

Get Going On Your Chicago Summer Bucket List Today!

Summer is short in the Windy City! Enjoy it while it lasts!

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Love and Shenanigans,


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