Northwest Chicago Adults Only Vacations
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Flight and Adults Only hotel deals in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,075
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
CA $1,199
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up.
Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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View all trips5* Adults Only holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,075
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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View all trips3 Night Adults Only holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,487
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
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See all available trips from Columbus to Northwest Chicago
View all trips4 Night Adults Only holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,892
per person
Nov 8 - Nov 12
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.
Reviewed on Oct 2, 2026
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See all available trips from Columbus to Northwest Chicago
View all tripsThings to do
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
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