
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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,101, price is now CA $778 per person
CA $778
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on Jul 11, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,912, price is now CA $1,393 per person
CA $1,393
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Perfect location Perfect view excellent staff fun time had by wife for her birthday great little getaway thanks
Reviewed on Jul 11, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $3,029, price is now CA $2,213 per person
CA $2,213
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026

The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,375, price is now CA $1,034 per person
CA $1,034
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
Very nice rooms and excellent service. Our stay could not have been better!
Reviewed on Jul 11, 2026

Club Quarters Hotel Wacker at Michigan, Chicago
Downtown Chicago
Price was CA $1,166, price is now CA $878 per person
CA $878
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,343 reviews)
Everyone was great. The location was fantastic. An elevator was down and they are not large to begin with. Only having the one elevator to service 10 floors was a bit rough. There were often lines waiting to take the elevator up or down. I'm sure they are working on it and it likely won't impact guests in the near future.
Reviewed on Jul 11, 2026
5* Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Nobu Hotel Chicago
Downtown Chicago
Price was CA $1,333, price is now CA $1,088 per person
CA $1,088
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,414, price is now CA $1,812 per person
CA $1,812
per person
Sep 18 - Sep 21
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST
Reviewed on Jul 10, 2026

The Langham, Chicago
Downtown Chicago
Price was CA $2,106, price is now CA $1,720 per person
CA $1,720
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Fantastic staff, beautiful property. Highly recommend the club lounge
Reviewed on Jul 10, 2026
3 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,612, price is now CA $1,124 per person
CA $1,124
per person
Sep 12 - Sep 15
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on Jul 11, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,822, price is now CA $1,326 per person
CA $1,326
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,912, price is now CA $1,393 per person
CA $1,393
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Perfect location Perfect view excellent staff fun time had by wife for her birthday great little getaway thanks
Reviewed on Jul 11, 2026
4 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,010, price is now CA $2,133 per person
CA $2,133
per person
Sep 14 - Sep 18
found 4 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Perfect location Perfect view excellent staff fun time had by wife for her birthday great little getaway thanks
Reviewed on Jul 11, 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 ...
9/10 Wonderful! (2,364 reviews)
"every one was really nice and helpful especially jerry the front desk guy. some of the rooms could have been cleaned a little better but this is a older hotel so i’m not really complaining i would stay here again"
Reviewed on Jul 11, 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 ...
9.2/10 Wonderful! (1,332 reviews)
"Perfect stay. Great gym!"
Reviewed on Jul 10, 2026

Hotel Chicago West Loop, SureStay Collection by Best Western
1622 W Jackson Blvd Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.2/10 Very good! (1,127 reviews)
"Renovado y limpio, el metro esta en corto"
Reviewed on Jul 11, 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.
Things to do

Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend

Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
More vacations you might like
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