Illinois Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Illinois
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,097, price is now CA $819 per person
CA $819
per person
Apr 17 - Apr 20
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions
Reviewed on Mar 15, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,547, price is now CA $1,344 per person
CA $1,344
per person
May 21 - May 24
found 17 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,275, price is now CA $1,147 per person
CA $1,147
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Wish there was microwaves in rooms
Or atleast the suits
Reviewed on Mar 16, 2026
3 Night Pet-friendly holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,097, price is now CA $819 per person
CA $819
per person
Apr 17 - Apr 20
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions
Reviewed on Mar 15, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $829 per person
CA $829
per person
Apr 17 - Apr 20
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
4 Night Pet-friendly holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,820, price is now CA $1,442 per person
CA $1,442
per person
Apr 22 - Apr 26
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions
Reviewed on Mar 15, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,929, price is now CA $1,662 per person
CA $1,662
per person
May 21 - May 25
found 13 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
Pet-friendly Hotels in Illinois
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is CA $167 per night from Apr 7 to Apr 8
CA $167
CA $196 total
Apr 7 - Apr 8
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (3,930 reviews)
Clean room and bathroom
Reviewed on Mar 18, 2026
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
The price is CA $156 per night from Mar 22 to Mar 23
CA $156
CA $183 total
Mar 22 - Mar 23
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,136 reviews)
Drinks where good The view of the room was very nice
Reviewed on Mar 17, 2026
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
The price is CA $197 per night from Mar 29 to Mar 30
CA $197
CA $275 total
Mar 29 - Mar 30
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
9.4/10 Exceptional! (3,322 reviews)
The hotel staff were great. We were even given recommendations. There was not a microwave in the room at this hotel, but they brought one up to us. This hotel is perfectly located and it’s very cool clean. The views from the room were beautiful.
Reviewed on Mar 17, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
