Plan a trip to see Wintrust Arena

Price found within the past 48 hours. Click for updated prices.

JW Marriott Chicago

Downtown Chicago

CA $707

per person

May 1 - May 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (1,000 reviews)

Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

Level Chicago – Old Town

Downtown Chicago

CA $930

per person

Mar 21 - Mar 27

found 9 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

The Wade

Downtown Chicago

CA $1,178

per person

Apr 27 - May 3

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

8.4/10 Very Good! (1,444 reviews)

The view from my room was stunning

Reviewed on Feb 7, 2026

Tours & day trips

See all 153 activities

Flyover in Chicago

Free cancellation available

Private & custom tours

See all 58 activities

Chicago Cocktail Adventure Part 1

Free cancellation available

Food, drink & nightlife

See all 23 activities

Chicago's Chinatown Food and Walking Tour

Free cancellation available

Attractions

See all 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 13 activities

BYOB Spray Paint and Sip at Studio W.I.P.

Free cancellation available

Popular places to visit

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Chess Records Building / Blues Heaven

You can spend time exploring the galleries in Chess Records Building / Blues Heaven during your travels in Chicago. While in this vibrant area, you can savor the top-notch restaurants.

Willie Dixon's Blues Heaven

You can learn about the history of Chicago with a visit to Willie Dixon's Blues Heaven. Stroll along the lakeside or visit the notable monuments in this vibrant area.

South Asia Institute

You can spend time studying the exhibits at South Asia Institute in Chicago. While in this vibrant area, you can savor the top-notch restaurants.

Elbridge G Keith House

Learn about the local history of Chicago when you take a trip to Elbridge G Keith House. Amble around this vibrant area's lakeside or experience its fascinating museums.