How to Spend Your Time in Chicago During the Summer

How to Spend Your Time in Chicago During the Summer: 10 Things to Do in Chicago

Now that summer is in full swing, travel season is too. Have you planned out which exciting city you're heading to next? New York, Paris, London, Los Angeles... All great cities. But they have nothing on CHICAGO in the summer.

Ask anyone who has been to or lives in Chicago during the summer and they'll tell you that all those cold winter months are worth living through solely because of the summer. Now I might be a littttlee biased, but I'm tell you--something about this city totally comes alive in the summer! It's like all of those months in hibernation puts us into action from late spring through early fall.

From rooftop bars to street festivals, the Riverwalk to Millennium Park, there are endless things to find, do, and eat here. If you're planning a trip to the Windy City during the summer, check out these tips on things to do in Chicago during your visit! Think of this as your "Chitown Summer Bucket List"!


1. Stroll down the Chicago Riverwalk

The city of Chicago recently invested a pretty penny into designing an amazing waterfront pedestrian walkway that is located on the south bank of the Chicago River. Visitors can come and enjoy a walk down by the river and stop in at the local wineries, restaurants, boat rental shops, bike rental stations, and more. You're right in the heart of downtown, which is wonderful to experience on a sunny day.


2. Head to Millennium Park for Free Activities

Millennium Park is sometimes scoffed off by locals as a tourist trap; but not in the summer! In the summer, Millennium Park has so much to offer visitors of all ages. There are free yoga and dance classes, free movies screenings, free concerts, free festivals, and more! What's better than free activities in the city?! For a full list of their activities from May through September, click right here


3. Visit Lincoln Park, the Zoo, and the Conservatory (all for free)

One of the city's best kept gems lies just north of the city center. The neighborhood of Lincoln Park is a must see when visiting Chicago (and it's where I call home!). Walk through the gorgeous park, visit the city's Lincoln Park Zoo, explore the Lincoln Park Conservatory, or relax by the Alfred Caldwell Lily Pool--all for free. It's a serene escape from the city without even having to leave the city. Try walking around the neighborhood if you have some time as well. It's very family friendly and full of boutiques, bars, and restaurants!


4. Shop the Farmer's Markets

There's something so nostalgic about a farmer's market in the summertime... Don't you agree? Chicago offers plenty of opportunities for farmers markets all around the city during the summer on various days of the week. You're guaranteed to get the extremely fresh food, beautiful flowers, and a lively atmosphere. There are even local restaurants that offer pop-ups at the markets from time to time! Check out the farmer's market schedule right here.


5. Attend a Festival

"Chicago" and "Festivals" are basically synonymous in the summer months. You can find a festival or event going on almost every single day in the summer--especially on the weekends. Attend fun events like Lollapalooza, Jazz Fest, Chicago Pride, West Fest, Taste of Chicago (or Randolph, River North, etc.), Art Fest, and even Hot Dog Fest. There are tons of different food, music, drink, or art related festivals going on throughout the summer, so make sure you don't miss out! Check out a full schedule here


6. Spend a Day On the River

If you're keen on spending the entire day by the water downtown, check out some of the other activities to do besides just the Riverwalk. You can go kayaking in the river, rent a boat or pontoon to cruise along the river, or you can take the uber-popular Chicago Architecture Tour. You basically get to spend the afternoon in a boat cruising around the downtown Chicago area while learning about the city around you. There are a few different companies that offer a Chicago River tour and, from what I hear, you really can't go wrong with any of them. Jay and I did one that was sponsored by the Chicago History Museum and it included a wonderful tour plus free drinks and snacks. I highly recommend it!


7. Drink at a Rooftop Bar and Eat on a Restaurant Patio

Ok, so I get that for those of you who live in warm climates you're probably thinking this one is silly; but in Chicago, rooftops and patios are a way of life in the summer. Like I said earlier, we're in hibernation mode during most of the year, so the minute it warms up--we are outside! 

Most restaurants and bars will start to open up their patio areas as soon as it hits decent temperatures (sometimes 50 degrees will do it), so take advantage of those when you can! See my list of places to eat in Chicago right here.

As for the best rooftops, check out some of these: J. Parker, Soho House, NoMI Garden, Cindy's, GreenRiver, Streeterville Social, or Rock Bottom. You can also browse the popular lists on Thrillist, Timeout, or Chicago Mag for more suggestions!


8. Spend the Day at the Beach

A lot of people look at me crazy when I say they should spend a day on the beach in Chicago, but it's a real thing that people do here! Thanks to Lake Michigan, Chicago's lakefront offers a nice stretch of "beachfront" property for visitors and locals to enjoy. You can party hard with the young crowd down by Oak Street Beach or North Avenue Beach (not my scene at all), or head a little further north towards Fullerton Beach or Montrose Beach to have a more quiet and relaxing experience. I personally love doing the latter with a little picnic in tow. Either way, I recommend you walk along the lakefront to take in the incredible views of the city and enjoy the lively atmosphere. 


9. See a Show

Chicago is an artistic hub for fascinating shows and brilliant performances. When visiting the city, you should definitely try to nab some tickets to see a Broadway play, a theatre performance, a dance performance, a comedy show, or a musical! The options are endless here and you shouldn't miss out.

My personal favorites are the dance performances put on by Giordano Dance Chicago, which is America's original jazz company. First of all, I love that the roots of jazz dance are here in Chicago and that this company has been thriving for over 50 years. Second, having grown up as a dancer myself, it's so inspiring to see the these incredibly talented professionals perform such moving pieces time and time again. I'm always so thrilled to see the new and innovative performances that their company comes up with! They typically have performances towards the beginning and end of summer (as well as throughout the rest of the year), and you can see their full schedule right here!


10. Explore the Neighborhoods

The Windy City is a neighborhood city, which means it's comprised of a ton of different areas and neighborhoods that all have their own unique personalities and vibes. The best part about being in Chicago when it's warm out is that you can actually enjoy the feeling of walking around and exploring the neighborhoods! Hop on a the L, take a bus, rent a bike, or get in a cab and head to a neighborhood that you want to see and explore it for a day. My personal favorites are Lincoln Park, Lakeview, Wicker Park, West Loop, and River North, but everyone has their preferences. You can check out more info on neighborhoods in my Chicago City Guide.


Also try:

  • Renting a Divvy bike and ride around town
  • Catching a baseball game with the Cubs or White Sox
  • Heading to Navy Pier to ride the new ferris wheel, or seeing the fireworks on Wednesdays and Saturdays
  • Exploring our world renowned museums, like the Art Institute or Shedd Aquarium
  • Renting a boat and venture out to Lake Michigan or tie-up to other boats in the "Play Pen"


This list is just barely scratching the surface on all the incredible things there are to do here during the summer. Comment below with more activities that you love in Chicago!


Want more info on what to do during your visit to Chicago? Check out my complete FREE City Guide on Chicago. You'll find tips on airports, transportation, where to stay, when to visit, and much more!


Similar Posts For You