Chicago in summer: best things to do and see

Chicago is a great city for a summer vacation. It is famous for its delicious cuisine, bold architecture, and fascinating history.

If you're visiting Chicago in summer, you should add cruises to your must-do activities. Viewing the city on a boat is one of the best experiences you will have in the city.

Couples will also find Chicago summer activities pleasant. They can learn about the city on a speedboat as they take in the thrill of the water.

Families shouldn't shy away from Chicago tours in the summer. If you have kids, consider going for guided tours through The Pedway. To learn more about the city, you can also learn about famous gangster hangouts or take Segway trips.

Create your Chicago summer itinerary full of activities that appeal to you with our top experiences below.

Best outdoor activities


1. Explore downtown Chicago through The Pedway

Do you find amazing architecture fascinating? Then you need to take a tour through the famous underground tunnels known as The Pedway. On the tour, you will see the city from a new perspective as you experience beautiful architectural interiors from above and below the ground.


This tour is led by a trained and experienced guide. In case of cold or rainy weather, you will get many indoor stops to warm up.

Address and opening hours:

120 North LaSalle, 120 N La Salle St, Chicago, IL 60602, USA. Open Thursday-Sunday from 2:00 PM.


2. Sample Chicago's delicious foods in a guided tour

Chicago is famous for its deep-dish pizza, hotdog, and brownies. This 2.5-hour walk goes through the most iconic spots of the city and includes stops during which you get to taste some of the must-try foods of Chicago.


Participants in this tour will take part in a Facebook photo contest, so brush up on your photography skills.

Address and opening hours:

410 N Michigan Ave, Chicago, IL 60611, USA. Open Monday-Sunday from 11:30 AM.


3. Listen to true tales of Chicago's gangster past in the Gangsters and Ghosts Walking Tour

The history of the criminal world of Chicago is absolutely fascinating. In this 2-hour walking tour, you will go through the Congress Hotel and other places that Al Capone frequented, learning about this famous gangster.


A trained historian will host this tour. Children under the age of 6 can join the walk for free.

Address and opening hours:

71 E Wacker Dr, Chicago, IL 60601, USA. Open Monday-Sunday, 11:00 AM-10:00 PM.


4. Watch the city from the lakefront in the Segway tour

If you're looking for a more leisurely tour, you can take the Segway along Chicago's lakefront. You will take in some amazing views of the skyline, Buckingham Fountain, and other iconic places.


You will get to ride the Segway i2. The trip begins with a quick training session on how to use this futuristic transport method before embarking on the tour.

Address and opening hours:

34 S Michigan Ave, Chicago, IL 60603, USA. Open from 10:30 AM-7:00 PM.


5. Bike to your chosen city attractions

Biking can be a good workout and great fun. For this experience, you have to get a full-day or half-day bike rental. You can then create your own itinerary and visit the attractions that you find most interesting.


You will receive a detailed map and can cycle along Lake Michigan or Lincoln Park. The available bike hire options include an electric bike and a Fuji Sportif 2.1 road bike.

Address and opening hours:

540 N Lake Shore Dr, Chicago, IL 60611, United States. Open Monday-Sunday from 9:00 AM.


6. Taste the finest Chicago pizza on a guided walking tour

Your Chicago summer guide should also include a pizza-tasting walking tour. During this experience, you will taste Chicago deep-dish pizza, as well as Neapolitan, artisanal, and Roman styles of pizza.


The tour is organized for small groups. You will get to visit 4 highly-rated pizzerias in Downtown Chicago and sample their offerings.

Address and opening hours:

465 N McClurg Ct, Chicago, IL 60611, USA. Open Wednesdays and Fridays from 1:30 PM.

Best water activities


7. Experience Chicago's breath-taking architecture on a cruise

This cruise covers all of Chicago's famous architectural highlights. The guides will go over the 100-year history of the skyline. You can choose the open-air decks or climate-controlled interiors.


The tour is conducted by friendly and experienced tour guides. Bartenders are available to provide you with refreshments.

Address and opening hours:

400 N Michigan Ave, Chicago, IL 60611, USA. Open Monday-Sunday from 9:30 AM-9:45 PM.


8. Enjoy wine, beer, cheese, and a BBQ on the Thursday Evening Cruise

For a relaxing evening, you can take a cruise on the Chicago River and Lake Michigan. You will admire the amazing city views as you glide over the water. The trip includes local wine tastings or some local beers. You'll be able to pair these refreshments with cheese or BBQ and sides.


The cruise lets you watch the sunset from the river and would be a great activity for a romantic getaway.

Address and opening hours:

400 N Michigan Ave, Chicago, IL 60611, USA. Every Thursday from 5:45 PM.


9. Enjoy the thrill of a speedboat ride

Your list of Chicago summer activities has to include a speedboat ride. An experienced guide will give you interesting details on Chicago's history and architecture throughout the ride. You will also get to see the most interesting waterfront landmarks of the city.


The ride has an Extreme Thrill Ride Option that offers high speeds and 360-degree spins.

Address and opening hours:

600 E Grand Ave, Chicago, IL 60611, USA. Open Monday-Friday from 11:00 AM.


10. Enjoy a romantic and serene evening cruise on Lake Michigan

Chicago in summer is quite romantic. Lake Michigan can be very calm in the evening and would make for a romantic cruise. You'll be able to watch the sun setting behind the skyline. A local guide will give brief commentaries as the tour goes on, but most of the trip will be spent with no narration.


The cruise has a full-service cash bar that offers local beers and spirits. You can also pose for photos at the picturesque stern.

Address and opening hours:

400 Michigan Ave, Chicago, IL 60611, USA. Open Monday-Sunday from 7:30 PM.


1. Where can I go swimming or relax by the water in Chicago?

North Avenue Beach is a great place to go for a swim. Located on the Near North End, it is popular among locals and visitors alike.

2. Are there any great summer festivals in Chicago?

The Chicago summer guide is always updated with the latest summer festivals. The events include the Chicago Blues Festival, the Chicago Air and Water Show, and the Chicago House Music Festival.

3. What are the must-visit outdoor attractions in Chicago?

The biggest outdoor attractions in this city are the Art Institute of Chicago, the Navy Pier, the Millennium Park, and the Shedd Aquarium.

4. What are some great day trips to take from Chicago in summer?

You can take a cruise on Lake Michigan or walk in the underground Pedway.

5. What are some fun activities with kids in Chicago in summer?

If you have kids, you can take a cruise over Lake Michigan, enjoy a lakefront Segway tour, or visit the zoo.