Plan a trip to see Flat Iron Building

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The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

CA $823

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,992 reviews)

Wonderful hotel and great atmosphere!

Reviewed on Sep 10, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,443

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,714 reviews)

We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).

Reviewed on Sep 8, 2025

Arlo Chicago

Downtown Chicago

CA $852

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,844 reviews)

Had an important meeting and was expecting the restaurant to be open on time at 7:00am…it opened at 7:20….very convenient place…one staff could have been nicer and more welcoming…felt like a burden when we checked in

Reviewed on Sep 9, 2025

Tours & day trips

See all 167 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 33 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

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