Booked a room for my cousins bachelorette party and it did not disappoint!! The amount of space, the luxurious feel, the bathroom!!!! The mattresses, I need in my house. I had the best sleep ever. Everything was perfect and the staff was amazing!!! Would definitely stay here again.

Reviewed on Sep. 5, 2025

Pendry Chicago

4.5 out of 5

Downtown Chicago

Price was CA $1,226, price is now CA $815 per person

CA $815

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,070 reviews)

Great place esp last minute

Reviewed on Sep. 5, 2025

Palmer House a Hilton Hotel

4 out of 5

Downtown Chicago

Price was CA $956, price is now CA $659 per person

CA $659

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (1,917 reviews)

Everything just fantastic at the Palmer house! A must place to stay in Chicago!

Reviewed on Sep. 5, 2025

Swissotel - Chicago

4.5 out of 5

Downtown Chicago

Price was CA $1,370, price is now CA $977 per person

CA $977

per person

Oct 5 - Oct 8

found 15 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (2,713 reviews)

Very good hotel and very good staff

Reviewed on Sep. 4, 2025

Sofitel Chicago Magnificent Mile

4.5 out of 5

Downtown Chicago

Price was CA $949, price is now CA $696 per person

CA $696

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,130 reviews)

Very nice and welcome staff we will return

Reviewed on Sep. 4, 2025

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5* Adventure holidays in Chicago

Price found within the past 48 hours. Click for updated prices.

Four Seasons Hotel Chicago

5 out of 5

Downtown Chicago

Price was CA $1,832, price is now CA $1,493 per person

CA $1,493

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,003 reviews)

I loved it all. Brought my 5 year old grandson Mateo and they catered to him including their kid room key card , a treasure chest choice, a hat and stuffed animal and his own kid sized robe. He spilled some food in restaurant and we apologized profusely, but they waved it off saying they were family friendly. Loved the pool, loved the hot tub, loved how kind and friendly staff was

Reviewed on Aug. 14, 2025

The Peninsula Chicago

5 out of 5

Downtown Chicago

Price was CA $2,067, price is now CA $1,527 per person

CA $1,527

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

Truly enjoyed our experience at this hotel. Staff very kind and helpful. Location was perfect because of its location on the Magnificent Mile and getting to other areas of interest in Chicago. The room was very comfortable and clean. Definitely recommend this hotel!

Reviewed on Sep. 4, 2025

The Ritz-Carlton, Chicago

5 out of 5

Downtown Chicago

Price was CA $1,656, price is now CA $1,530 per person

CA $1,530

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,003 reviews)

Too expensive for such a basic room. Cheap towels and toilet paper. Broken wall switches. Handle on bathroom door broke. Just a basic room with nothing special. No refrigerator or microwave. For almost $5000 for just 3 nights I had to pay for valet parking and all food (not even free snacks). Complimentary breakfast would have been great for $5000. Bathroom was nice but just a waste of money. Not sure what all the money was for. Will not recommend or ever go back.

Reviewed on Sep. 1, 2025

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