
West Side Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in West Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North
Downtown Chicago
Price was CA $899, price is now CA $694 per person
CA $694
per person
Apr 23 - Apr 26
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
room was great and staff were always great help
Reviewed on Feb 14, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,267, price is now CA $866 per person
CA $866
per person
Apr 23 - Apr 26
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Rooms were great and breakfast was delicious
Reviewed on Feb 14, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,084, price is now CA $799 per person
CA $799
per person
Apr 23 - Apr 26
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.
Reviewed on Feb 9, 2026

Stay One Chicago
Downtown Chicago
Price was CA $3,061, price is now CA $2,385 per person
CA $2,385
per person
Apr 28 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 2026

Hyatt Regency Deerfield
Price was CA $1,067, price is now CA $832 per person
CA $832
per person
Apr 24 - Apr 30
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,007 reviews)
nice large room with updated decor, gorgeous bath with super White, clean, fresh towels and linens on the bed!
Reviewed on Feb 1, 2026
5* Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

The Langham, Chicago
Downtown Chicago
Price was CA $1,407, price is now CA $1,104 per person
CA $1,104
per person
Mar 23 - Mar 26
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Best service in Chicago — whether desk service, room service, etc. Stunning property. Amazing bathtubs.
Reviewed on Feb 12, 2026

Park Hyatt Chicago
Downtown Chicago
Price was CA $3,206, price is now CA $2,509 per person
CA $2,509
per person
Apr 28 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Everything was great… but the staff was absolutely amazing!
Thank you for taking such great care of us.
Reviewed on Jan 24, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was CA $1,792, price is now CA $1,452 per person
CA $1,452
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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
3 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,084, price is now CA $799 per person
CA $799
per person
Apr 23 - Apr 26
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.
Reviewed on Feb 9, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,267, price is now CA $866 per person
CA $866
per person
Apr 23 - Apr 26
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Rooms were great and breakfast was delicious
Reviewed on Feb 14, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,598, price is now CA $1,193 per person
CA $1,193
per person
Mar 19 - Mar 22
found 1 hour 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
4 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,092, price is now CA $747 per person
CA $747
per person
Apr 2 - Apr 6
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.
Reviewed on Feb 9, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,737, price is now CA $1,124 per person
CA $1,124
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Rooms were great and breakfast was delicious
Reviewed on Feb 14, 2026

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,183, price is now CA $876 per person
CA $876
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Staff was great. The hotel is quirky and cool with an unbeatable location right in the middle of shopping, theater and restaurants. Easily walkable to the Art Institute and Millennium Park. The rooms are not large, and could use some new furniture, but very clean.
Will definitely be back.
Reviewed on Feb 14, 2026
Pet-friendly Hotels in West Side

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,962 reviews)
Clean room, comfortable bed, friendly staff, good location
Reviewed on Feb 10, 2026

The Emily Hotel
311 North Morgan Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9/10 Wonderful! (1,296 reviews)
Beautiful
Reviewed on Feb 11, 2026

Hyatt House Chicago West Loop
105 N MAY STREET Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,186 reviews)
Great and easy. Walkable neighborhood
Reviewed on Feb 10, 2026
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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