Northwest Side Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,469, price is now CA $930 per person
CA $930
per person
Mar 21 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,282, price is now CA $1,494 per person
CA $1,494
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
Pendry Chicago
Downtown Chicago
Price was CA $1,424, price is now CA $972 per person
CA $972
per person
Mar 21 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
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View all trips5* Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,282, price is now CA $1,494 per person
CA $1,494
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 Langham, Chicago
Downtown Chicago
Price was CA $2,301, price is now CA $1,625 per person
CA $1,625
per person
Mar 21 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Gorgeous property, facilities, and location.
Reviewed on Feb 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,083, price is now CA $1,551 per person
CA $1,551
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
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View all trips3 Night Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $959, price is now CA $673 per person
CA $673
per person
Apr 22 - Apr 25
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,057, price is now CA $824 per person
CA $824
per person
Apr 24 - Apr 27
found 4 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
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See all available trips from Columbus to Northwest Side
View all trips4 Night Pet-friendly holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,237, price is now CA $873 per person
CA $873
per person
Apr 20 - Apr 24
found 16 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Clean room, good views, was complicated getting in, because the front door was closed and had to go through parking lot. Disappointed there was no free bottle of wine as promised. Other then that no complaints.
Reviewed on Feb 4, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,282, price is now CA $1,494 per person
CA $1,494
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) 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
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View all tripsPet-friendly Hotels in Northwest Side
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Chicago IL
Book a stay at this family-friendly apartment in Chicago. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Portage Park and Copernicus Center ...
10/10 Exceptional! (116 reviews)
Jamie was extremely welcoming and accommodating. Super cozy place with fun special touches. Would love to come back!
Reviewed on Feb 2, 2026
3BR Spacious Home Away From Home. Coziest neighborhood in Chicago.
Chicago IL
Stay at this apartment in Chicago. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wrigley Field and United Center are located ...
9.8/10 Exceptional! (37 reviews)
Every thing was clean. The location is excellent with comfortable beds.
Reviewed on Jan 6, 2026
Sleeps 22 • Modern Multi-Unit • Gym • Workspaces
Chicago Illinois
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
