Far Southeast Side Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
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 3 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
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,203, price is now CA $2,019 per person
CA $2,019
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug. 27, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,154, price is now CA $754 per person
CA $754
per person
Nov 6 - Nov 9
found 11 hours ago
Roundtrip flight included
Toronto (YTO) 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
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View all trips5* Pet-friendly holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago
Downtown Chicago
Price was CA $1,648, price is now CA $1,100 per person
CA $1,100
per person
Nov 20 - Nov 23
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 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 3 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
Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all trips3 Night Pet-friendly holidays in Far Southeast 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 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on Aug. 27, 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 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
I can honestly say that this hotel exceeded all expectations. Everything was fabulous
Reviewed on Sep. 1, 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 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Room was very nice and clean. Great location and we were able to walk almost everywhere we wanted to go. Staff was friendly and knowledgeable. Only thing I would say is that it is a little loud at night but you are downtown right off Michigan ave so you should expect some street noise. Would definitely stay here again.
Reviewed on Sep. 2, 2025
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View all trips4 Night Pet-friendly holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,831, price is now CA $1,198 per person
CA $1,198
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.
Reviewed on Aug. 24, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $2,061, price is now CA $1,276 per person
CA $1,276
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
The Langham, Chicago
Downtown Chicago
Price was CA $2,247, price is now CA $1,478 per person
CA $1,478
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
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View all tripsPet-friendly Hotels in Far Southeast Side
Admiral Motel By Oyo Chicago I-94
9118 S Cottage Grove Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Chicago Museum of Science and Industry and Jackson ...
Spacious 4-bedroom house in fabulous Chicago Back Yard Pond, and Theatre
Chicago
Stay at this vacation home in Chicago. Enjoy laundry facilities, in-room jetted tubs, and an in-room coffeemaker. Popular attractions Chicago Museum of Science ...
Cozy 4/5BR haven near 95th station. Ideal for friends, family, biz & more!
Chicago
Book a stay at this family-friendly vacation home in Chicago. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Chicago Museum of ...
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.