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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 14 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 14 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,602 reviews)

Loved the hotel, the only negative thing I have to say is that I found it to be odd that there is no trash bags used in the trash cans in the rooms. Also, the bathroom has no vent for exhaust fan. Other than that, everything else was excellent, very clean facility, great breakfast selection.

Reviewed on 4 Nov 2025

Arlo Chicago

Downtown Chicago

Save 100% on your flight

HK$4,069

per person

25 Dec - 31 Dec

found 14 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 153 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

Marina City

You can learn about the history of Chicago when you stop by Marina City. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

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.

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.

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.

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.

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.