Northwest Side Adults Only Vacations
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Flight and Adults Only hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,332, price is now CA $909 per person
CA $909
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Staff was extremely accommodating. The breakfast was extraordinary. Hotel cleanliness was superb. Thanks for a wonderful stay.
Reviewed on Mar 18, 2026
La Banque Hotel
Price was CA $1,265, price is now CA $882 per person
CA $882
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (469 reviews)
Room was amazing and beautiful and comfortable
Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous
Reviewed on Mar 1, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,804, price is now CA $1,358 per person
CA $1,358
per person
May 21 - May 25
found 2 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,628, price is now CA $1,323 per person
CA $1,323
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,844 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,299, price is now CA $2,023 per person
CA $2,023
per person
May 21 - May 25
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (798 reviews)
I really enjoyed my stay at Nobu. The food was very nice and the atmosphere was what I really wanted (the main reason I chose to stay there). I also really liked the location of the hotel. Everything was very walkable and I enjoyed exploring when I had free time. My only thoughts as negatives are the view from the rooms are not super impressive, I had opted in for the upgraded room at a discounted price which I did get (but wasn’t informed that when I checked in which was stated when I opted in), and I had quite a few issues with the Wi-Fi and working the tv so I just gave up on that. If you’re looking for a reliable, clean place that offers a lot for food and beverages then I’d definitely recommend staying!
Reviewed on Mar 15, 2026
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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,332, price is now CA $909 per person
CA $909
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Staff was extremely accommodating. The breakfast was extraordinary. Hotel cleanliness was superb. Thanks for a wonderful stay.
Reviewed on Mar 18, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,513, price is now CA $1,155 per person
CA $1,155
per person
May 22 - May 25
found 2 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
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See all available trips from Columbus to Northwest Side
View all trips4 Night Adults Only holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $1,265, price is now CA $882 per person
CA $882
per person
May 25 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (469 reviews)
Room was amazing and beautiful and comfortable
Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous
Reviewed on Mar 1, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,656, price is now CA $1,121 per person
CA $1,121
per person
May 21 - May 25
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Room was great but there was a boat docked right outside and it kept slamming into the dock all night which was very loud. Just not great sound-proofing on the rooms on that side of the hotel. Otherwise we had a great stay.
Reviewed on Mar 18, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,804, price is now CA $1,358 per person
CA $1,358
per person
May 21 - May 25
found 2 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer
Reviewed on Mar 17, 2026
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