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Arlo Chicago

Downtown Chicago

€565

per person

10 Nov - 16 Nov

found 1 day 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 1 day 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 1 day 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 152 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 24 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

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

Cadillac Palace Theatre

You can get tickets for a performance at Cadillac Palace Theatre on your trip to Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Chicago City Hall

Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.

333 West Wacker Drive

After visiting 333 West Wacker Drive, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Willis Tower

4.5/5(81 reviews)

Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.

Chicago Loop Synagogue

Chicago Loop Synagogue is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Richard J. Daley Center

Richard J. Daley Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or visit the notable monuments in this vibrant area.