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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 10 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 10 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,602 reviews)

We got a room with a great view! The staff were all very pleasant and attentive.

Reviewed on 3 Nov 2025

Arlo Chicago

Downtown Chicago

Save 100% on your flight

HK$4,069

per person

25 Dec - 31 Dec

found 10 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 142 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 45 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 24 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 10 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

63rd Street Beach

Why not spend a lazy afternoon at 63rd Street Beach during your trip to Chicago? Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Griffin Museum of Science and Industry

4.5/5(23 reviews)

This large, interactive museum contains a coal mine and World War II submarine among its many attractions.

Robie House

Witness the simple beauty of Frank Lloyd Wright’s designs in a Chicago house that epitomizes a popular American style of architecture.

University of Chicago

4/5(15 reviews)

Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Bob-O-Link Meadow

Enjoy an outing to Bob-O-Link Meadow during your stay in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Jackson Park Driving Range

You can take time to visit Jackson Park Driving Range during your travels to Chicago. Make time to visit the shops and churches while you're in the area.