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The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

CA $477

per person

Nov 21 - Nov 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,992 reviews)

We had to park our car in front of the valet section in front of the hotel. Part of the problem was that the block where hotel parking was used was blocked off due to skyscraper glass. Traffic was terrible. One of the valet workers told us we would probably be okay to leave the vehicle there and go ahead and check in. Upon checking in I was given a room key. The key wouldn't work. Kim (was awesome) was very responsive and delivered us working room keys. Unfortunately, when we walked into the room it was already occupied. Kim took us back to the lobby and upgraded us to a suite. She took us to the suite and everything was fine. Then, we left the hotel just a few minutes later and were shocked to see that our car had been given a parking ticket. Otherwise, the room was great and staff was very attentive. We just felt there were things beyond our control that affected the beginning of our stay.

Reviewed on Sep. 7, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,032

per person

Nov 21 - Nov 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,714 reviews)

Location, cleanliness, and friendly staff

Reviewed on Sep. 7, 2025

theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $580

per person

Nov 21 - Nov 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,014 reviews)

Matthew at the front desk was great & he made our stay better than we could’ve expected. The food from the restaurant was amazing (highly recommend the wings) and the bartenders are wonderful! Our room was a dream! 100/10! ⭐️ We will definitely be returning for our next Chicago stay!

Reviewed on Sep. 5, 2025

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Free cancellation available

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360 CHICAGO Observation Deck

Free cancellation available

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Free cancellation available

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