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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 4 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 4 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 4 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

Wrigley Building

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Magnificent Mile - River North featuring night scenes, a city and signage

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Shops at Northbridge

You can find the perfect gifts to bring home at Shops at Northbridge during your trip to Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.

Michigan Avenue Bridge

Learn about the local history of Chicago when you take a trip to Michigan Avenue Bridge. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Shops at North Bridge

Spend a day exploring the department store, luxury fashion outlets and food court at this mall on the glitzy Magnificent Mile shopping district.

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.