
Central Chicago Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,415, price is now CA $1,015 per person
CA $1,015
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay.
Reviewed on Jul 2, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,038, price is now CA $1,377 per person
CA $1,377
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,608, price is now CA $1,112 per person
CA $1,112
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026


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View all trips5* Pet-friendly holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was CA $1,683, price is now CA $1,449 per person
CA $1,449
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Arrived 4:30PM, room not ready. Left bags with Bell Desk and went to a business dinner. Returned at 8pm, Bell Desk could not find my bags. Arrived an hour later, they had put them in the wrong room. No offer of any kind to remedy or try to remedy, just “sorry”. Shameful.
Reviewed on Jul 3, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,998, price is now CA $1,556 per person
CA $1,556
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The shower temp was about on the hot side no matter how low you had it. The bed& room were overall great
Reviewed on Jul 3, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,075, price is now CA $1,679 per person
CA $1,679
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.
Reviewed on Jul 2, 2026
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See all available trips from Columbus to Central Chicago
View all trips3 Night Pet-friendly holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,415, price is now CA $1,015 per person
CA $1,015
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay.
Reviewed on Jul 2, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,608, price is now CA $1,112 per person
CA $1,112
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026

Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips4 Night Pet-friendly holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,699, price is now CA $1,160 per person
CA $1,160
per person
Aug 26 - Aug 30
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
We had a wonderful stay! The hotel was very clean, and the staff who checked us in and out were incredibly kind and welcoming. The location was perfect—we were able to walk everywhere we wanted to go, which made our trip so convenient. I would definitely stay here again!
Reviewed on Jul 2, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,038, price is now CA $1,377 per person
CA $1,377
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

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See all available trips from Columbus to Central Chicago
View all tripsPet-friendly Hotels in Central Chicago

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,676 reviews)
"The TV did not work and we called the front desk 10 times without any help. There were not enough towels for 2 people and no coffee/tea for the room."
Reviewed on Jul 3, 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
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! (4,483 reviews)
"A lot of it was good, the rooms were very good. The AC was very good and the view from the bedroom. The only things I want to complain about is the expensive stuff and the TV in the bedroom not working/turning on. It costs a lot of money for car parking. The beds were one of the most comfortable ..."
Reviewed on Jul 3, 2026

Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,834 reviews)
"We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay."
Reviewed on Jul 2, 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

Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend

Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
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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.








