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

Field Museum of Natural History

from $72.08

First Lady Cruises Chicago

from $28

Wendella Cruises Chicago

from $28

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

4.9(386)

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

4.9(256)

$45

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

Observation Decks

Skydeck Chicago Tickets

4.2(29)

from

$42.33

Free cancellation

Field Museum of Natural History entrance with columns and banners in Chicago.

Museums

Field Museum of Natural History Tickets

NEW

$72.08

Free cancellation

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

Observation Decks

360 Chicago Sip & View

4.2(10)

from

$44

Selling out fast

Guest viewing Chicago skyline from lakefront during Skydeck and Architecture Cruise tour.

Guided Tours

Chicago Skydeck & Architecture Cruise with Small Group Guided Tour

NEW

$129

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

4.7(56)

$45

Millions love heading out with us

David

United States

Oct 2025

5/5

‌

This was just a lifetime experience. It was like rediscovering the whole history of Chicago in less than a hour. Perfect date with my girlfriend. We learned a lot while having hun.

45-min Chicago River Architecture Cruise

Megan

United States

Oct 2025

5/5

‌

I had the best time with my grandfather on the cruise. He is older and struggles with mobility. This was the best way for him to see the city. Very relaxing. Our tour guide was extremely informative. #1 tourist attraction in Chicago

90-min Chicago River Architecture Cruise

Andrew

United States

Jul 2025

5/5

‌

+2 more

The walk through introduction of the Willis tower and chicago history was informative and fun to learn with the artistic layout. The elevator was cool watching the numbered floors go up and down as you learn more trivia facts of the elevator and Willis tower from the screened walls. Then the sky deck floor has a phenomenal ambiance for buying merchandise and the breathtaking views of the highest sky deck in the USA. I recommend this to anyone of all walks of life

Skydeck Chicago Tickets

Suryanarayana

Oct 2025

5/5

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