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 $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,768, price is now CA $1,221 per person
CA $1,221
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
What a great excellent and friendly welcome front desk personnel. The lady on who worked on Saturday afternoon was amazing. Didn’t catch her name but she was very nice and welcoming
Reviewed on Jul 5, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
5* Pet-friendly 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 $2,000, price is now CA $1,528 per person
CA $1,528
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Excellent service. Room was fantastic with an incredible view of the city. Definitely worth every penny! Will go back for sure!
Reviewed on Jul 9, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $3,181, price is now CA $2,523 per person
CA $2,523
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Fantastic staff, beautiful property. Highly recommend the club lounge
Reviewed on Jul 10, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,569, price is now CA $2,080 per person
CA $2,080
per person
Sep 3 - Sep 7
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
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 $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026
4 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 $1,737, price is now CA $1,169 per person
CA $1,169
per person
Sep 11 - Sep 15
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,933, price is now CA $1,370 per person
CA $1,370
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 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! (2,360 reviews)
"We enjoyed our trip was very clean and helpful staff"
Reviewed on Jul 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 ...
9.2/10 Wonderful! (1,331 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! (1,123 reviews)
"The room was small but clean. The bed seemed smaller than a double but wasn't a big deal. The staff were very friendly and helpful. I was there to go to the University of Chicago hospital, which was very close by. The hotel parking is $25, however I parked in the lot next door for $11 all night."
Reviewed on Jul 9, 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
Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $71
per adult
94% of travellers recommend
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.
