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Visitor's Guide to Summer in Chicago

Updated: December 22, 2023
 By Mel

Chicago is a fun and family-friendly city to visit this summer. There are plenty of tun and free things to do all around the city, and this is your guide to enjoying the best of Chicago this summer. 


This is a Top 10 list of things to do in Chicago this summer. For more ideas on popular things to do in Chicago, check out our posts on bus tours and walking tours of the city.

Some of the items listed in this post are included for free with the purchase of a tourist discount pass


1.  Take a Tour!

The best way to get out and enjoy the sunshine in Chicago this summer is to take a tour. Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, the Riverwalk, and specialty tours like an evening Ghost Tour to learn about Chicago's Haunting History.

One of our most popular summer tours is our Chicago Architecture tour, Birth of a Skyscraper.



Explore Chicago by Boat, Bus, Segway, and Bike

If you’re not up for walking, there are many ways to explore the city.

2. Check out  Navy Pier

Head out to Navy Pier this summer, which boasts one of the best views of our skyline. It's a great place to walks around, see free concerts and attend events, and watch fireworks. During the summer, Navy Pier offer free fireworks every Wednesday and Saturday!  Join our Twilight Riverwalk & History tour on Wednesday or Saturday nights, which ends near the path to Navy Pier.

You can also take a self-guided walking tour and learn about the history of this area, which has evolved since its construction in 1914 but still remains a summer hotspot in Chicago.

You can look up a full list of events in here and better plan your visit.

For a list of more free things to do in Chicago this summer, check out the Free Things section below. 

3. Explore a Famous Park

Chicago is known for our beautiful public parks all around the city. Some of the most popular parks are downtown in the front yard of Chicago. 

Millennium Park is wonderful to explore with our self-guided tour.  You will find beautiful art, fountains, and a lovely silver bridge that will bring you to one of our newest downtown parks, Maggie Daley Park. This one's for the young at heart with a carnival type theme. It has a skating ribbon (free with your own skates), play structures, and an enchanted forest for kids to roam through. 

Farther south, you will find Grant Park which boasts artwork, a skate park, and of course, Buckingham Fountain. Our Chicago Architecture tour ends here.

Lincoln Park is excellent for spotting statues and for those who adore history! Visit on our guided tour, Lincoln Park Blues & Gangster Tour.



For other free things to do in Chicago, check out our Free section below.

4. Catch a Concert

Summer is concert season, and there are plenty of great shows going down in Chicago this summer. Going to a concert is a great way to cap off an evening after spending the day touring Chicago. Some big names coming to Chicago this summer:



For a list of more things to do at night in Chicago this summer, check out our Things to Do at Night post.

Chicago also has some free and family-friendly concerts and festivals, which you can check out in the Festival section below.

5. BikeChicago bikers waterfront skyline  Along the Lake Shore Drive Path

Lake Shore Drive is a bike path that runs 18 miles along Lake Michigan and it a great place to bike and enjoy the summer in Chicago. 

There are a number of places to rent a bike from. Take in the views of the city from a unique and local perspective.

 Give our self-guided bike tour a try!

6. Sports

Chicago boasts a number of great professional sports teams. Depending on what time of year you're visiting, there's bound to be a great game going on.

Summer in the city means baseball, and you can catch the Chicago Cubs are playing at Wrigley Field all summer long. This is a great way to spend an afternoon with the kids, and you can get your tickets here.

For more ideas on family-friendly things to do in Chicago, check out the section below.  

chicago farmers market 7. Head to a Chicago Farmers Market

(Thursdays, 7-2pm, May-October)

Throughout the summer and early fall, you can find farmer’s markets in many corners of the city- even in the Loop! 

It is a great chance to grab a mid-day snack, buy some fresh produce, or to find a neat artesian craft.

Admission is free and there is no better way to appreciate a community than to sample the local produce! 

 8. Have a Drink!

Escape the summer swelter by going out after dark- for cocktails! Chicago has speakeasies – fitting for the mobster history of the Windy City.

Chicago also has a number of great rooftop bars, a great way to relax and enjoy the view of the city. 

In our Guide to Chicago Bars you can find out about historic bars, game bars and where to have a pint while playing some trivia. If you’re looking for more than just atmosphere and want to find one of the best craft beers, we can make sure you find a local pint.

9.  Chicago Summer Dance

Wednesdays- Sundays, June 27-August 24, 2019



Show off your dance moves or come to learn new ones at the Music Garden in Grant Park this summer in Chicago. With over 40 different live bands and DJs to get your boogie on, you can be one step closer to being like Bob Fosse, who was a Chicago native before he jazz handed his way into our hearts.

The event is free, and you can also just come to enjoy the music if you forgot your dancing shoes at home. 

10. Look into a Tourist Discount Pass

Visitors who are working with a budget should think about getting a Chicago tourist pass. These services provide heavy discounts at some of the most popular attractions in the city.

Here are a few of the sites you can visit with various discount passes, which a focus on great summer time activites such as:

These are just a few of the activities you can enjoy. If you plan to visit even a few of these attractions, you could easily end up saving a lot of money over general admission prices.

Tourist Passes Reviewed

For more details, make sure to read our full post covering Chicago tourist passes.

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Many of our Top Ten are great activities for children, like going to  Navy Pier, but check out our post about Family Friendly Activities in Chicago for a more complete guide.  Below you will find a couple of other options to keep your children entertained this season!

See an Outdoor Movie

Chicago presents movies in all of our neighborhood parks, including Wicker Park.  Mid-June through August, you can expect to find a free movie most days of the week. 

On Tuesday nights, you can watch a movie in Millennium Park at Pritzker pavilion with crowds of other eager Chicagoans.  This is one of the best parks to enjoy a movie since it is downtown with an incredible backdrop: the Chicago Skyline.

Check out the Museums

Museums are great places to go to escape the summer heat and cool off a bit while still having plenty to see and do.

While Chicago has a number of museums to enjoy, there are some kid-friendly ones like the Adler Planetarium, the Children's Museum, and the Money Museum are just a few to name. 

Stroll Along our Favorite Paths

Chicago is lucky to have amazing places to leisurely hike throughout the city.  The Riverwalk, the Lakefront, the 606- to name a few. The Riverwalk is bustling with restaurants that offer local beers and tasty snacks while gazing at the buildings that line the Chicago River. The 606 is a new path built on a retired elevated train track designed by James Corner. 

If you truly love the outdoors, check out the Chicago Park District for more trails!

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There are many free activities to take advantage of in Chicago during every season of the year.  Many of our Top Ten are also free to explore, like the number of parks all around the city, but below you will find a couple of other free options this month. Check out our comprehensive post about the Top Free Things to Do in Chicago for more ideas.

AON Fireworks

After spending the day exploring  Navy Pier, catch a beautiful firework display with the Aon fireworks. This spectacular show on Lake Michigan takes place bi-weekly on Wednesdays and Saturdays all summer long from Memorial Day through Labor Day.

In the summer our Michigan Avenue and Navy Pier tour ends just in time to catch the show!

Millenium Park Summer Music Series

June 13- August 15, 2019

If you enjoy live music you should attend the Millennium Park Summer Music Series. It's free weekly concerts at Pritzker Pavilion showcasing a broad range of musicians, both established and emerging. You can bring a blanket and a picnic and lounge in the grassy section or grab a seat in the front to make this the perfect date night!

Click here for a list of the summer lineup and look into other things to do in Millennium Park, including our walking tours.

Join a Free Outdoor Workout Class

Chicago's popular free summer workout series returns to Millennium Park. From the end of May through August there are a number of workouts you can choose from. 


  • Tuesdays & Thursdays - Yoga at 7:30am.
  • Saturdays - Tai Chi @ 7am, Yoga @ 8am, Pilates @ 9am, and Zumba @ 10am.

Come out and get your sweat on!

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Packing to go to a city you've never been to can feel daunting- how much is too much? There's also the fear of meeting unexpected weather and not having packed something essential. Below are some FAQ about packing we want to answer for you:
  • Does it rain a lot in the summer? June is the wettest month all year, so be sure to have an umbrella on hand. Otherwise, the weather is sunny, hot, and humid.
  • What to pack: The summer temperatures can get pretty high so be sure to pack light, breathable clothes. An umbrella is handy for summer showers, but it will be too hot for a rain jacket. However, you might want to bring along a cardigan or light sweater you can easily slip on if you're going into museums, as it might be a bit chilly coming into the air-conditioned buildings. We have a post on weather in Chicago if you'd like to read more in depth. 
  • Be sure to bring water with you. A lot of the public parks have removed water fountains due to health concerns, so bringing water along prevents you from having to buy expensive water in shops and keeps you hydrated.
  • Going out for a drink or nice restaurant in the evening? If you've been walking around outside all day it might be best to pack along a nice change of clothes. Most places in Chicago are pretty casual in dressing, but if you're going out at night to somewhere ritzy like a speakeasy, dressing up a bit is best.

We have a monthly post section below if you want to read up more on the specifics of the weather to better decide what clothes to bring on your summer trip to Chicago.

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Most Chicago festivals are free to attend and we have LOTS of them throughout the year.  There are nearly 100 festivals in Chicago in the summer.  There are food festivals, beer festivals, tequila festivals, music festivals, and art festivals. There is a fest for every type of visitor.  Below are a list of our most popular and free summer festivals as well as links to Things to Do for summer holidays:

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To learn more about what do to in specific months here in Chicago, click the links below:

About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: December 22nd, 2023
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