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Arlo Chicago

Downtown Chicago

€565

per person

10 Nov - 16 Nov

found 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,826 reviews)

I wish that all the staff was more accommodating! some of them were some were not!

Reviewed on 6 Oct 2025

Pendry Chicago

Downtown Chicago

€678

per person

10 Nov - 16 Nov

found 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on 7 Oct 2025

Swissotel - Chicago

Downtown Chicago

€694

per person

10 Nov - 16 Nov

found 20 hours ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Tours & day trips

See all 158 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

South Wentworth Street

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

Illinois Institute of Technology

Explore the campus of Illinois Institute of Technology as part of your travels around Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

McCormick Tribune Center

You can find out about the history of Chicago with a visit to McCormick Tribune Center. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Theatre on the Lake

You can make plans for a show at Theatre on the Lake on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Stephen A. Douglas Tomb and Memorial

Find out about the history of Chicago when you spend time at Stephen A. Douglas Tomb and Memorial. Experience the entertainment choices and fascinating museums in this vibrant area.