Chicago, United States

Chicago for first-timers

Welcome to Chicago! Dive into the city's vibrant culture and explore must-see attractions. Our expertly curated tours will ensure you make the most of your inaugural visit.

Couple examining a map in a city setting, ideal for first-time visitors.

Top things to do

360 Chicago

from $30

Chicago River Architecture Cruises

from $32.50

Willis Tower Skydeck Tickets

from $42.33

First Lady Cruises Chicago

from $28

Wendella Cruises Chicago

from $28

Chicago Architecture Center

from $7

Top experiences in Chicago

Free cancellation

Chicago River cruise boat passing under DuSable Bridge with city buildings in the background.

Sightseeing Cruises

90-min Chicago River Architecture Cruise by Wendella

$45

90-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 409 ratings.From $45

Free cancellation

Chicago River cruise boat passing under a bridge with city skyline.

Sightseeing Cruises

45-min Chicago River Architecture Cruise by Wendella

from

$28

45-min Chicago River Architecture Cruise by Wendella. Rated 4.9 out of 5 from 648 ratings.From $28

Free cancellation

Chicago River architecture cruise boat passing under a lift bridge with city skyscrapers in the background.

Sightseeing Cruises

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

$45

90-min Chicago River and Lake Michigan Architecture Cruise by Wendella. Rated 4.7 out of 5 from 63 ratings.From $45

View from the Skydeck at Willis Tower, Chicago, overlooking the cityscape.

Observation Decks

Skydeck Chicago Tickets

from

$42.33

Skydeck Chicago Tickets. Rated 4.7 out of 5 from 122 ratings.From $42.33

Free cancellation

Family enjoying view from Chicago 360 Observation Deck with city skyline.

Observation Decks

360 Chicago Sip & View

from

$44

360 Chicago Sip & View. Rated 4.2 out of 5 from 17 ratings.From $44

Lake Michigan Cruise. Rated 4.7 out of 5 from 94 ratings.From $32.50

Free cancellation

Guided group walking under Calder's Flamingo sculpture in Chicago.

Museums

Architecture Center Admission with Must-See Chicago Walking Tour

$35

Architecture Center Admission with Must-See Chicago Walking Tour. Rated 0 out of 5 from 0 ratings.From $35

What our guests say

Ariana V

United States

Solo

Last week

Funny and engaging tour guide. Lovely views, especially on the cruise at sunset. I learned so many cool facts and have shared them with my friends and family. Money well spent!

45-min Chicago River Architecture Cruise by Wendella

Sarantuya B

United States

Group

2 weeks ago

We just came from Mongolia. Visit the skydeck. We did very enjoyed our time there . It's beautiful place i would love the place. We have small businesses in our country, we did beautiful pictures for our business product. Thankyou Chicago!

Skydeck Chicago Tickets

Chetna D

United States

Couple

Dec 2025

+1 more

I absolutely loved this tour! The JBL speakers were fantastic and made it so easy to hear the guide clearly, even in a busy and noisy environment. The tour guide was incredibly knowledgeable and shared information in such a fun, engaging, and effortless way that it really stayed with me. I still remember interesting facts like the Chicago River being 22 feet wide and how it turns green on St. Patrick’s Day. The clear sound from the JBL speakers and the amazing guide together made this tour truly memorable and enjoyable.

90-min Chicago River Architecture Cruise by Wendella

Suryanarayana M

Group

Oct 2025

I absolutely loved my experience on the Wendella Chicago River Architecture Cruise! The tour was both relaxing and educational, offering an incredible perspective of Chicago’s iconic skyline and its rich architectural history. Cruising through the river gave me a completely different appreciation of the city’s design — from the classic art deco buildings to the stunning modern skyscrapers. What I enjoyed the most was seeing the downtown view open up as we entered Lake Michigan — the panoramic view from the water was breathtaking. The guide was knowledgeable and engaging, making the entire journey both fun and insightful. A truly memorable Chicago experience!

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