
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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $920, price is now CA $680 per person
CA $680
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
The staff was incredible, they went out of their way to assist and resolve immediately with any issues we had. Marina, Terina, Gazelle, Nicky and the engineer were all great, incuding the cleaning staff. Breakfast and coffee and fruit were fantastic. Will definitely recommend to family and friends and visit again, if we come into the city.
Reviewed on Jun 28, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $3,418, price is now CA $2,268 per person
CA $2,268
per person
Sep 12 - Sep 18
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $3,637, price is now CA $2,438 per person
CA $2,438
per person
Sep 12 - Sep 18
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,573, price is now CA $1,113 per person
CA $1,113
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $3,517, price is now CA $2,629 per person
CA $2,629
per person
Sep 12 - Sep 18
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable.
The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.
Reviewed on Jun 21, 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.

Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,062, price is now CA $1,684 per person
CA $1,684
per person
Aug 5 - Aug 8
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
Shower bombs would be a good incentive. Really enjoyed the scenery as well as the customer service.
Reviewed on Jun 27, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,152, price is now CA $1,692 per person
CA $1,692
per person
Aug 5 - Aug 8
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The Trump hotel is always impeccable and this time was no different. We did bring our newborn (first time parents) and they were beyond accommodating; they provided us a crib.
Reviewed on Jun 28, 2026

Park Hyatt Chicago
Downtown Chicago
Price was CA $4,475, price is now CA $3,708 per person
CA $3,708
per person
Sep 12 - Sep 18
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent hotel and location. 1 min away from Michigan avenue
Reviewed on Jun 23, 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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $920, price is now CA $680 per person
CA $680
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
The staff was incredible, they went out of their way to assist and resolve immediately with any issues we had. Marina, Terina, Gazelle, Nicky and the engineer were all great, incuding the cleaning staff. Breakfast and coffee and fruit were fantastic. Will definitely recommend to family and friends and visit again, if we come into the city.
Reviewed on Jun 28, 2026


The Emily Hotel
Downtown Chicago
Price was CA $1,667, price is now CA $1,248 per person
CA $1,248
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Clean and Helpful Staffs. You have to look for your parking space, mostly are street parking, but there is a valet at the hotel if you asked for it.
Reviewed on Jun 28, 2026
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View all trips4 Night Adults Only holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.


Level Chicago - River North
Downtown Chicago
Price was CA $2,771, price is now CA $1,956 per person
CA $1,956
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,573, price is now CA $1,113 per person
CA $1,113
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
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See all available trips from Columbus to Northwest Chicago
View all tripsThings to do

Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend

Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
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