Plan a trip to see University of Illinois Chicago

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Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Downtown Chicago

per person

26 Jul - 29 Jul

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.6/10 Exceptional! (1,011 reviews)

Clean and we loved the king size bed! We had a great dinner at Gino’s East across the road. So easy to get to the subway and wherever you wanted to go. Loved the coffee and water available in the lounge area. Close walk to Tilly’s bagels which I recommend!

Reviewed on 29 Apr. 2024

JW Marriott Chicago

Downtown Chicago

per person

26 Jul - 29 Jul

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,002 reviews)

The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on 14 Apr. 2024

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

26 Jul - 29 Jul

Return flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (1,152 reviews)

Amazing. Definitely coming back!

Reviewed on 20 Apr. 2024

Tours & day trips

See all 225 activities

Architecture River Tour from Navy Pier

Free cancellation available

Private & custom tours

See all 55 activities

Chicago Private Instagram Car Tour (Private & All-Inclusive)

Free cancellation available

Food, drink & nightlife

See all 41 activities

Chicago Favourites Food & Walking Tour plus Free Bike/Kayak Rental

Free cancellation available

Attractions

See all 17 activities

Chicago CityPASS®: Experience 5 must-see attractions

Free cancellation available

Classes & workshops

See all 13 activities

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Popular places to visit

Mary Bartelme Park

Explore the great outdoors at Mary Bartelme Park, a lovely green space in Chicago. Experience the fascinating museums and acclaimed art galleries in this vibrant area.

311 S Wacker Dr

You can learn about the history of Chicago with a trip to 311 S Wacker Dr. Experience the fascinating museums and acclaimed art galleries in this vibrant area.

Sears Tower

4.5/5(39 reviews)

The Skydeck at Willis Tower offers the best place in Chicago for a bird’s eye view across the breadth of the city and Lake Michigan.

Chicago Board of Trade Building

You can learn about the history of Chicago when you stop by Chicago Board of Trade Building. Experience the entertainment choices and fascinating museums in this vibrant area.

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.

Jane Addams' Hull-House Museum

You can enjoy some culture when you stop by Jane Addams' Hull-House Museum in Chicago. Discover the entertainment choices and notable monuments in this vibrant area.