
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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,483, price is now CA $994 per person
CA $994
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The staff did not explain that room cleaning was available only upon request. For the breakfast specialty coffee you had to wait for the front desk staff to be available.
Reviewed on Jul 6, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,057, price is now CA $1,243 per person
CA $1,243
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 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 – Old Town
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location.
The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.
Reviewed on Jul 6, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $2,167, price is now CA $1,473 per person
CA $1,473
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,957, price is now CA $1,387 per person
CA $1,387
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Beautiful hotel! Right on the pier near everything! Included were activity and food credits. Limited amenities (no pool or hot tub and never found the gym) but we were near so much it didn’t matter. Highly recommend
Reviewed on Jul 6, 2026
5* Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Nobu Hotel Chicago
Downtown Chicago
Price was CA $2,230, price is now CA $1,813 per person
CA $1,813
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (879 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

Four Seasons Hotel Chicago
Downtown Chicago
Price was CA $5,906, price is now CA $4,268 per person
CA $4,268
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!
Reviewed on Jul 6, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,660, price is now CA $2,003 per person
CA $2,003
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The best hotel we have ever stayed at!
Reviewed on Jul 6, 2026
3 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,188, price is now CA $866 per person
CA $866
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The staff did not explain that room cleaning was available only upon request. For the breakfast specialty coffee you had to wait for the front desk staff to be available.
Reviewed on Jul 6, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,394, price is now CA $1,008 per person
CA $1,008
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,541, price is now CA $1,118 per person
CA $1,118
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 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
4 Night Pet-friendly holidays in West Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,483, price is now CA $994 per person
CA $994
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The staff did not explain that room cleaning was available only upon request. For the breakfast specialty coffee you had to wait for the front desk staff to be available.
Reviewed on Jul 6, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,057, price is now CA $1,243 per person
CA $1,243
per person
Sep 24 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 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 – Old Town
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location.
The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.
Reviewed on Jul 6, 2026
Pet-friendly Hotels in West Side

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,341 reviews)
"D"
Reviewed on Jul 6, 2026

The Emily Hotel
311 North Morgan Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9.2/10 Wonderful! (1,325 reviews)
"Great boutique hotel in a great location! Definitely will stay here again when visiting Chicago."
Reviewed on Jul 5, 2026

Hotel Chicago West Loop, SureStay Collection by Best Western
1622 W Jackson Blvd Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.2/10 Very good! (1,116 reviews)
"Fantastic Staff"
Reviewed on Jul 5, 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
More vacations you might like
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