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 $45

Willis Tower Skydeck Tickets

from $42.33

First Lady Cruises Chicago

from $28

Wendella Cruises Chicago

from $28

Chicago Architecture Center

from $15

Top experiences in Chicago

Free cancellation

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

Sightseeing Cruises

45-min Chicago River Architecture Cruise

from

$28

45-min Chicago River Architecture Cruise. Rated 4.9 out of 5 from 509 ratings.From $28

Free cancellation

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

Sightseeing Cruises

90-min Chicago River Architecture Cruise

$45

90-min Chicago River Architecture Cruise. Rated 4.9 out of 5 from 322 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 105 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 3.9 out of 5 from 13 ratings.From $44

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

$45

90-min Chicago River and Lake Michigan Architecture Cruise. Rated 4.7 out of 5 from 56 ratings.From $45

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

Ashleigh

United States

Jan 2026

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I loved this experience! I went alone and all of the employees were super kind and welcoming. I haven't been to the skydeck in over 10 years so it was great to go back and see the amazing views of Chicago!!

Skydeck Chicago Tickets

Sweta

United States

Jan 2026

‌

My mom is visiting Chicago for first time and taking her to the cruise and showing her the city was one of thing on my bucket list.

45-min Chicago River Architecture Cruise

Chetna

United States

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

Suryanarayana

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