Plan a trip to see Wintrust Arena

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Fairmont Chicago at Millennium Park

Downtown Chicago

CA $746

per person

Jul 9 - Jul 12

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (2,137 reviews)

Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,194

per person

Jun 18 - Jun 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,478 reviews)

A unique experience, loved being on the pier! Stunning views of the lake!

Reviewed on May 2, 2026

La Banque Hotel

CA $768

per person

Jun 11 - Jun 15

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (484 reviews)

small town main street neighborhood, good food nearby, shopping

Reviewed on May 1, 2026

Tours & day trips

See all 213 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 51 activities

Sip Happens: Chicago Loop Prohibition Tour

Free cancellation available

Food, drink & nightlife

See all 32 activities

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Attractions

See all 22 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 15 activities

Chicago: BYOB Spray Paint and Sip Workshop

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.

South Wentworth Street

You can find the perfect gifts to bring home at South Wentworth Street during your stay in Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

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.