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theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

HK$3,910

per person

25 Dec - 31 Dec

found 6 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on 20 Oct 2025

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

HK$4,661

per person

25 Dec - 31 Dec

found 6 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,602 reviews)

The staff here was super friendly and helpful! Loved how they decorated the lobby for Halloween. Overall a great hotel.

Reviewed on 3 Nov 2025

Arlo Chicago

Downtown Chicago

Save 100% on your flight

HK$4,069

per person

25 Dec - 31 Dec

found 6 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

Great staff. Especially front desk and restaurant! Great location.

Reviewed on 3 Nov 2025

Tours & day trips

See all 152 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 49 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 12 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Chicago Cultural Center

You can enjoy a show at Chicago Cultural Center during your trip to Chicago. Amble around this vibrant area's riverfront or experience its entertainment choices.

Marshall Field Building

You can learn about the history of Chicago with a trip to Marshall Field Building. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

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.

Carbide and Carbon Building

After visiting Carbide and Carbon Building, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Cloud Gate

You can learn about the history of Chicago with a visit to Cloud Gate. Discover the fascinating museums and notable monuments in this vibrant area.

James M. Nederlander Theatre

You can make plans for a show at James M. Nederlander Theatre on your trip to Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.