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Arlo Chicago

Downtown Chicago

€565

per person

10 Nov - 16 Nov

found 1 hour 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 hour 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 hour ago

Return flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

Great views. Really helpful staff.

Reviewed on 7 Oct 2025

Tours & day trips

See all 155 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 28 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 26 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Milwaukee Avenue

You can search for that perfect souvenir at Milwaukee Avenue during your trip to Chicago. Experience the live music and theatre scene in this vibrant area.

Community First Medical Center

If Community First Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Chicago.

Six Corners

You can browse for the perfect souvenirs at Six Corners during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

The Gift Theatre

You can make plans for a show at The Gift Theatre during your stay in Chicago. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area.

Copernicus Center

You can make plans for a show at Copernicus Center during your stay in Chicago. Amble around this vibrant area's lakeside or attend a sporting event.

Northwestern College Chicago Campus

Walk around the campus at Northwestern College Chicago Campus during your visit to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.