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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 20 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 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,602 reviews)

Room was perfect! Rooftop bar was on point and friendly staff

Reviewed on 4 Nov 2025

Arlo Chicago

Downtown Chicago

Save 100% on your flight

HK$4,069

per person

25 Dec - 31 Dec

found 20 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 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 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

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

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.

Bridgeport Art Center

You can spend time browsing the exhibits at Bridgeport Art Center during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Bubbly Creek

Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Stephen A. Douglas Tomb and Memorial

Find out about the history of Chicago when you spend time at Stephen A. Douglas Tomb and Memorial. Experience the entertainment choices and fascinating museums in this vibrant area.

Theatre on the Lake

You can make plans for a show at Theatre on the Lake on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.