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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 1 day 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 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,602 reviews)

Nice hotel, decent breakfast No room service

Reviewed on 4 Nov 2025

Arlo Chicago

Downtown Chicago

Save 100% on your flight

HK$4,069

per person

25 Dec - 31 Dec

found 1 day ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

Great view of the park and easy to walk around to so many things. Loved the amenities and the shower was particularly nice for a hotel bathroom! Staff were nice and accommodating.

Reviewed on 4 Nov 2025

Tours & day trips

See all 153 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 48 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 15 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

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Ida B. Wells-Barnett Residence

You can find out about the history of Chicago with a visit to Ida B. Wells-Barnett Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Eighth Regiment Armory

Find out about the history of Chicago when you spend time at Eighth Regiment Armory. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Supreme Life Building

You can find out about the history of Chicago with a trip to Supreme Life Building. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Grand Terrace Ballroom

Find out about the history of Chicago with a stop at Grand Terrace Ballroom. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

Victory Monument

You can find out about the history of Chicago with a visit to Victory Monument. Experience the acclaimed art galleries and fascinating museums in this vibrant area.