Things To Do In Chicago: Attractions, Tours, Activities in 2026

Top experiences in Chicago

Popular things to do in Chicago

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Open-top Big Bus Chicago tour in downtown with skyscrapers in the background.

Big Bus Chicago Hop-on Hop-off Toursfrom $49

Family enjoying the view from 360 Chicago observation deck.

360 Chicagofrom $27

Boats and kayaks on the Chicago River with city skyscrapers in the background.

Chicago River Architecture Cruise Ticketsfrom $30

Couple lying on glass ledge at SkyDeck, Willis Tower, overlooking Chicago skyline.

Willis Tower Skydeck Ticketsfrom $42.33

Chicago Riverwalk with 'Chicago's First Lady' tour boat passing by Marina City.

First Lady Cruises Chicagofrom $28

Tour boat on the Chicago River with downtown Chicago skyscrapers in the background.

Wendella Cruises Chicagofrom $28

People on a boat deck viewing Chicago skyline at dusk with water and cloudy sky.

Shoreline Cruises Chicagofrom $30

Chicago Architecture Center facade with city reflections and pedestrians.

Chicago Architecture Centerfrom $15

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Chicago Attractions

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What our guests say

Elisabetta B

2 weeks ago

The cruise is very, very well organized; the staff were punctual and professional. Above all, it is much more comprehensive than others, as it offers a view of the city from both the lake and the river. Truly spectacular. The guide on board was very knowledgeable. I highly recommend it.

Chicago River & Lake Sightseeing Cruise by First Lady

Anne M

United Kingdom

2 weeks ago

Jean, our guide, was fabulous! Such a wealth of knowledge conveyed in an interesting and humorous style. Thoroughly recommend!

Chicago Architecture Center River Cruise aboard First Lady

Callie M

United States

2 weeks ago

First time in Chicago. Decided to do this night one just to get a feel for the city. It was raining and the views were still amazing!

45-min Chicago River Architecture Cruise by Wendella

Michele S

United States

2 weeks ago

Our tour guide was very knowledgeable and entertaining. It was just the right amount of time. Everyone was helpful and friendly. Thank you!

75-Minute Chicago River Architecture Cruise by Shoreline

Samanth P

Canada

3 weeks ago

I had the best experience at the Skydeck Chicago. It was magical. I highly recommend going there and experiencing it. Also, Headout app made it easy to book tickets right from the comfort of your couch.

Skydeck Chicago Tickets

Michael S

United States

3 weeks ago

+1 more

I enjoyed going so far out into Lake Michigan for all the pictures I could handle of the Chicago coastline! It was absolutely beautiful! Did I mention this was the Night Cruise? It was beyond exquisite! It was so great, in fact, I had to video call my family and show them THIS part of my journey! They were so excited and impressed! Also, our guide Doug was awesome! The info and history he had about the various buildings and locations gave me the truest sense of a tour that kept me interested and wanting to come back for more! Thank you for bringing him on-board with us! Even with his mandated quota of bad jokes!

Chicago at Night: River & Lake Sightseeing Cruise by First Lady

Monica D

United States

3 weeks ago

We could not have had a better guide. Alex, you were amazing. Your knowledge and the way you are able to communicate it are top tier. You are witty and funny. Thank you for a wonderful experience.

90-min Chicago River Architecture Cruise by Wendella

Lori S

United States

3 weeks ago

Wendella boat tours are wonderful, I have been on several. My favorite is the Lake and River cruise. The Dosets are very knowledgeable about the city. The scenery of the downtown from the lake view is spectacular. I highly recommend this tour. It was my third this summer!

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella