30 Ideas For A Fun Chicago Summer

There’s nothing quite like summertime in Chicago. Street fests. Rooftops & beer gardens. Movies in the Park. The beach. The list goes on and on.

With that in mind, we’ve put together 30 of the best things to do in Chicago this summer. Be sure to let us know if there are any Chicago summer staples that we missed!

1. Taste the Rainbow Cone.

Pure bliss awaits you at the historic Rainbow Cone ice cream shop. You have to try the “Original Rainbow Cone”, a true Chicago staple.

2. Take in some sun at the beach.

Luckily for Chicagoans, we have a number of tremendous beaches at our disposal. Get your daily dose of Vitamin D by spending the day at any of Chicago’s many beaches.

3. Wine and dine at a rooftop bar.

When it comes to food and drinks, Chicagoans don’t mess around. Enjoy breathtaking views of the city while you eat and drink in style at any of the numerous rooftop bars in the Chicago area.

4. Attend a summer music festival.

Live music and summertime are synonymous.  Luckily for us, Chicago is a music hub! Throughout the summer there are numerous concerts and festivals taking place all throughout the city.  If you’d prefer the all-out festival experience be sure to check out summer’s last stand, North Coast Music Festival.

5. Attend a street festival.

Nobody does street fests like Chicago. It seems like every weekend during the summer there is a new street fest to check out with great local food & entertainment. Check out the Chicago street fest events calendar here. 

6. Hang out in a beer garden.

Summer in Chicago is a wonderful time, and there’s no better place to spend it than at a beer garden.  The city has numerous offerings, truly something for every kind of beer connoisseur.  Check out Gene’s Sausage Shop & Delicatessen for all the beer and sausage you can handle.

7. Find a patio with BYOB.

There’s nothing better than actually being able to eat outside, thankfully Chicago has a huge amount of restaurants and bars with outdoor seating.  We recommend checking out local favorite Irazu in Bucktown, where you can BYOB and the food is delicious.

8. Watch a movie in Millennium Park.

Every Tuesday night through September Millennium Park will be playing movies free for the public. Check out their schedule here to make sure you don’t miss out on any upcoming movies and family fun.

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9. Take a boat tour of Chicago.

There’s no better way to get a feel for the city than to tour it by boat.  That might not be completely true, but we love to be on the water any chance we get. Check out one of the many Chicago boat tours for a great Chicago experience.

10. Take a late night Chicago helicopter tour.

Now, this is the way to take in the city! Imagine flying over all the wondrous locations in the city and having that bird’s eye view. Head here for details on this unforgettable experience.

11. Make the trip to Six Flags Great America.

For the thrill seekers out there, there’s nothing better in the summertime than roller coasters and water rides. Luckily for us Six Flags Great America is just an hour away, a perfect day trip out of the city.

12. Play volleyball on the beach.

As previously mentioned, Chicago has a bevy of local beaches. Get your game on and check out volleyball at local beaches like North Avenue Beach.

13. Check out a local farmer’s market.

One of the most helpful things you can do is support your local farmers! Thankfully summertime presents an awesome opportunity for all the local farmers to come out and give the public a chance to buy some fresh produce. Check out the Chicago farmers market schedule here.

14. Catch a baseball game.

No matter what side you pledge your allegiance to, there’s one thing you can’t argue about.  Chicago summertime and baseball go hand in hand. Check out the Cubbies on the North Side or head down to the South Side to catch a Sox game.

15. Watch a drive-in movie at Cascade. 

Looking for that nostalgia feeling? Look no further than Cascade Drive-in! Enjoy movies like they used to back in the day, in your car with your loved ones. Just because this is an old school activity doesn’t mean the films are outdated! You can definitely catch the summer blockbusters here.

16. See the animals at the zoo.

There’s nothing better than being able to spend a sunny day among all the precious animals in the zoo. Whether it’s the Lincoln Park Zoo or the Brookfield Zoo, Chicago has options!

17. Bike Lake Shore Drive or the 606.

If exercise is your game or you simply just love riding your bike, you are in luck! Chicago has some tremendous opportunities for bike riding.  Whether it’s cruising along Lake Shore Drive or the newly opened 606, Chicago is a biker’s paradise.

18. Visit the Bean.

Sure it may be “touristy”, but a trip to see the Bean also means a trip to the Millennium Park area. Start your day off by checking out the Bean and then spend the rest of it hanging out in the park.  Sounds like a great summer day to us.

19. Take a ride on the Navy Pier Centennial Wheel.

Added in the summer of 2016 is the Centennial Wheel at Navy Pier! Take a ride in the new Centennial Wheel to get a breathtaking view of the city.

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20. Take a Segway tour of the city.

Take in the beauty of Chicago while putting in minimal effort. That sounds wonderful to us, and the Chicago Segway Tour certainly does not disappoint.  You’ll be surprised at how much you learn and see on these Segway tours!

21. Kayak the Chicago River.

Kayaking is tremendous exercise, but it is also an incredibly good time to share with your loved ones.  We can’t think of a better way to spend a sunny Chicago afternoon than kayaking down the Chicago River.  Check out Urban Kayaks for the chance to spend your day kayaking down the river.

22. Shop the Magnificent Mile.

You know Chicago, one of the best shopping towns in the world! There are endless amounts of stores along Chicago’s Magnificent Mile.  Everyone in your family is sure to find a store that they love on this magnificent stretch of shops.

23. Take a Chicago Pizza Tour.

Interested in enjoying some legendary Chicago but not sure which pizza place to choose? Don’t worry, Chicago Pizza Tours has you covered! With the tours offered, you’ll have the chance to check out four distinct pizzerias in four different neighborhoods. With this option, you’ll be a Chicago pizza expert in no time.

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24. Do yoga in Millennium Park.

Yogis rejoice, yoga in Millennium Park is actually a thing!  Before the summer ends make sure you get to the park and get your sweat on.  Yoga isn’t all though – Tai Chi, Pilates, and Zumba are also offered throughout the summer. Click here for more information on the schedule.

25. Find a neighborhood pool.

Not every Chicagoan is lucky enough to have a rooftop pool, thankfully Chicago has us less fortunate covered. Head here to find the closest local pool so that you and your family can get your swim on.

26. Rent or charter a sailboat.

Craving a day on the boat but don’t have a boat? Us too. Thankfully for us, there are great companies out there like Chicago Sailboat Charters who allow us to live out those boating dreams.

27. Journey to Oak Park to see Frank Lloyd Wright’s home and studio.

Make a day trip out to Oak Park to check out the magnificent architectural style of the great Frank Lloyd Wright! Whether you prefer a guided interior tour or a full-blown neighborhood tour, you definitely have options.  Head here to check out the tours available.

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28. Visit the Chicago Botanic Garden.

Become one with nature when you spend the day at the Chicago Botanic Garden. Walk through the gardens or tour them by tram, the possibilities are endless at this Chicago staple.

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29. Visit the Park at Wrigley.

New for this summer is the Park at Wrigley! The freshly created park right next to the friendly confines of Wrigley Field features yoga, movies, farmers markets, and just general family fun. Check out all that they have to offer here.

30. See the city from Skydeck Chicago.

Step outside the tallest building in the Western Hemisphere to get a better glimpse of this wonderful city. You’ll be 1,353 feet in the air, so you know the views are going to be absolutely spectacular. Head here for more information.

Written by @properties
@properties Christie’s International Real Estate is Chicagoland’s #1 brokerage. Through our affiliation with Christie’s International Real Estate, our network spans nearly 50 countries. No matter your real estate needs, we’ve got you covered.