West Side Adults Only Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by throwingsofas
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Adults Only hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,920, price is now CA $1,076 per person
CA $1,076
per person
Apr 22 - Apr 27
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The service was excellent, the rooms were clean and comfortable, and the breakfast buffet was also good. The bar in the lobby also served the best cocktails we had on the entire trip. The location was AMAZING, right off of Magnificent Mile! We were within 12 minutes walking time to 95% of the places we wanted to go. This hotel is great value for money.
Reviewed on Feb 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,919, price is now CA $1,141 per person
CA $1,141
per person
May 13 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,587, price is now CA $2,537 per person
CA $2,537
per person
Mar 31 - Apr 6
found 20 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,773, price is now CA $1,259 per person
CA $1,259
per person
May 13 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026
5* Adults Only holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,059, price is now CA $803 per person
CA $803
per person
Mar 22 - Mar 24
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,587, price is now CA $2,537 per person
CA $2,537
per person
Mar 31 - Apr 6
found 20 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $3,109, price is now CA $2,326 per person
CA $2,326
per person
Mar 31 - Apr 5
found 24 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The room was comfortable and beautiful design. Comfortable bed and bedding. Large desk. Good walkable location. But we could hear sirens at night
Reviewed on Feb 16, 2026
3 Night Adults Only holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,259, price is now CA $752 per person
CA $752
per person
May 12 - May 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The service was excellent, the rooms were clean and comfortable, and the breakfast buffet was also good. The bar in the lobby also served the best cocktails we had on the entire trip. The location was AMAZING, right off of Magnificent Mile! We were within 12 minutes walking time to 95% of the places we wanted to go. This hotel is great value for money.
Reviewed on Feb 20, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,407, price is now CA $1,102 per person
CA $1,102
per person
May 12 - May 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
4 Night Adults Only holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,895, price is now CA $1,101 per person
CA $1,101
per person
May 17 - May 21
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The service was excellent, the rooms were clean and comfortable, and the breakfast buffet was also good. The bar in the lobby also served the best cocktails we had on the entire trip. The location was AMAZING, right off of Magnificent Mile! We were within 12 minutes walking time to 95% of the places we wanted to go. This hotel is great value for money.
Reviewed on Feb 20, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,919, price is now CA $1,141 per person
CA $1,141
per person
May 13 - May 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
