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 $29

Chicago River Architecture Cruises

from $45

Willis Tower Skydeck Tickets

from $42.33

First Lady Cruises Chicago

from $28

Wendella Cruises Chicago

from $28

Top experiences in Chicago

Free cancellation

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

Observation Decks

360 Chicago Sip & View

4.2(10)

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

4.7(45)

$45

Free cancellation

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

Sightseeing Cruises

45-min Chicago River Architecture Cruise

4.8(217)

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

4.8(159)

$45

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

Observation Decks

Skydeck Chicago Tickets

4.4(22)

from

$42.33

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

Millions love heading out with us

Courtlyn

United States

Aug 2025

5/5

‌

We loved the moderator John, he was very informative and creative in his guided speech. His personality shined through in his jokes and our seats on the boat was perfect.

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

Yaumara

United States

Mar 2025

5/5

We visited Chicago for Valentine's Day, it was the best in spite of the cold and the snow. The viewpoint was incredible, the music was spectacular.

360 Chicago Sip & View

Joy

United States

Oct 2025

5/5

Enjoyed the tour guide and it was very interesting in learning about the history of the buildings in Chicago. We would reccomend it.

45-min Chicago River Architecture Cruise

Elia

United States

Sep 2025

5/5

We have taken this cruise many times, we take family and friends when they visit. We always learn something new. Our tour guide Kenny was amazing. Funny, amiable and very informative. Kudos!!

90-min Chicago River and Lake Michigan Architecture Cruise