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 – Old Town
Downtown Chicago
Price was CA $903, price is now CA $568 per person
CA $568
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.
Reviewed on Sep. 2, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,666, price is now CA $1,007 per person
CA $1,007
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Pendry Chicago
Downtown Chicago
Price was CA $1,042, price is now CA $655 per person
CA $655
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Fantastic experience top to bottom. The staff was incredible, the room was luxurious, and we couldn't have asked for a better place to stay. We will be back.
Reviewed on Sep. 3, 2025
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 $1,666, price is now CA $1,007 per person
CA $1,007
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
3 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $903, price is now CA $568 per person
CA $568
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
Everything was perfect. Be aware of the expensive it is to park in Chicago.
Reviewed on Sep. 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,666, price is now CA $1,007 per person
CA $1,007
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
Pendry Chicago
Downtown Chicago
Price was CA $1,042, price is now CA $655 per person
CA $655
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Fantastic experience top to bottom. The staff was incredible, the room was luxurious, and we couldn't have asked for a better place to stay. We will be back.
Reviewed on Sep. 3, 2025
4 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
Downtown Evanston
Price was CA $1,727, price is now CA $1,068 per person
CA $1,068
per person
Oct 10 - Oct 14
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!
Reviewed on Aug. 18, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,772, price is now CA $1,112 per person
CA $1,112
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,698, price is now CA $1,705 per person
CA $1,705
per person
Nov 3 - Nov 7
found 18 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Pet-friendly Hotels in West Side
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Level Chicago Fulton Market
354 North Union Avenue, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are ...
Hampton Inn & Suites Chicago Medical District UIC
710 S Seeley Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago ...
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.