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.
Hotel Lincoln
Lincoln Park
Price was CA $1,007, price is now CA $836 per person
CA $836
per person
May 5 - May 9
found 11 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
7.8/10 Good! (1,083 reviews)
Stayed at Hotel Lincoln and had a great experience overall! The location is fantastic—close to everything and perfect for exploring the area. The staff were incredibly friendly and welcoming, which really made the stay more enjoyable. The rooms were clean and comfortable. While the bathroom could use some updating, it didn’t take away from the overall positive experience. I’d definitely consider staying here again!
Reviewed on Mar 29, 2026
Kinzie Hotel
Downtown Chicago
Price was CA $1,491, price is now CA $1,160 per person
CA $1,160
per person
Jun 7 - Jun 10
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,878, price is now CA $1,492 per person
CA $1,492
per person
Jun 1 - Jun 5
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.
Reviewed on Mar 27, 2026
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,736, price is now CA $1,464 per person
CA $1,464
per person
Jun 1 - Jun 5
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Breakfast was delish! Staff was nice..great location.
Reviewed on Mar 31, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $2,568, price is now CA $2,197 per person
CA $2,197
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
The room was clean, comfortable, and well organized The location was perfect, close to restaurants and attractions
Reviewed on Mar 15, 2026
3 Night Pet-friendly holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
Price was CA $1,334, price is now CA $1,137 per person
CA $1,137
per person
Apr 30 - May 3
found 4 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
Room was clean but small. Extremely loud throughout the night hard to sleep not well insulated. Temperature fluctuates consistently throughout the day. High price on hidden charges and lost items using valet. Out dated elevators that need maintenance. Otherwise was good location to the heart of the city and very kind staff.
Reviewed on Mar 31, 2026
Kinzie Hotel
Downtown Chicago
Price was CA $1,491, price is now CA $1,160 per person
CA $1,160
per person
Jun 7 - Jun 10
found 11 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,552, price is now CA $1,217 per person
CA $1,217
per person
Jun 5 - Jun 8
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.
Reviewed on Mar 27, 2026
4 Night Pet-friendly holidays in Illinois
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Price was CA $1,212, price is now CA $897 per person
CA $897
per person
Apr 30 - May 4
found 16 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,878, price is now CA $1,492 per person
CA $1,492
per person
Jun 1 - Jun 5
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.
Reviewed on Mar 27, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,213, price is now CA $971 per person
CA $971
per person
Apr 30 - May 4
found 16 hours ago
Roundtrip flight included
New York (NYC) 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 $191 per night from Apr 12 to Apr 13
CA $191
CA $224 total
Apr 12 - Apr 13
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! (4,029 reviews)
There is NO AIR CONDITIONING in any room NONE then they ran out of fans! Expedia advertises it does have air conditioning. Don’t stay here!
Reviewed on Mar 30, 2026
River Hotel
75 East Wacker Drive Chicago IL
The price is CA $165 per night from Apr 26 to Apr 27
CA $165
CA $193 total
Apr 26 - Apr 27
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,046 reviews)
Great location. Room had a great setup for our family. Room and property showed signs of wear and tear, but nothing alarming or off putting.
Reviewed on Mar 30, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
The price is CA $152 per night from Apr 5 to Apr 6
CA $152
CA $179 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the ...
8.8/10 Excellent! (2,391 reviews)
Great stay, excellent service and friendly staff. Room had a beautiful view of East Grand Avenue on our side of the building. Breakfast was excellent. Parking was a bit pricey each day, other than that, no complaints.
Reviewed on Mar 31, 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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