Plan a trip to see Chicago Cultural Center

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Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,331

per person

Aug 11 - Aug 15

found 21 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (2,519 reviews)

Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.

Reviewed on Jun 4, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,378

per person

Aug 7 - Aug 10

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (481 reviews)

Very clean and loved the location and amenities with the store on the first floor was fantastic

Reviewed on Jun 3, 2026

Pendry Chicago

Downtown Chicago

CA $1,689

per person

Jul 23 - Jul 26

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (1,121 reviews)

I absolutely loved it! I little bit noisy but close to literally everything!

Reviewed on Jun 2, 2026

Tours & day trips

See all 244 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 57 activities

Chamarel 7 Colours and Waterfalls - Exclusive South West Tour

Free cancellation available

Chicago Chinatown: Dragon Kings Puzzle Adventure

Free cancellation available

Food, drink & nightlife

See all 36 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

See all 24 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

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Chicago: BYOB Spray Paint and Sip Workshop

Free cancellation available

Popular places to visit

Cloud Gate

You can learn about the history of Chicago with a stop at Cloud Gate. Discover the acclaimed art scene and notable monuments in this vibrant area.

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Chicago Theatre

See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.

Chicago Skyline Aerial Sunrise Sunset Cityscape Panorama

State Street

During your visit to Chicago, you can search for that perfect souvenir at State Street. Experience the acclaimed theater scene and entertainment choices in this vibrant area.

Beautiful Chicago Skyline. Gorgeous photo of a Chicago Skyline as viewed from the Museum Campus Lakefront Trail.

Aon Center

Aon Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed theater scene in this vibrant area.

Chicago Riverwalk

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.