Find Cat & Dog Friendly Hotels in Westchester from S$111

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Pet friendly Hotels

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Westchester pet-friendly hotels

Breakfast and dinner served
Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook
3.0 star property
Westchester
8.6 out of 10, Excellent, (1010)
"Thanks, great stay"
United States
Robert
The price is S$145
includes taxes & fees
6 Jan - 7 Jan, 2026
Four Points by Sheraton Chicago Westchester/Oak Brook
Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2665)
"It's an excellent place."
United States
Jose
The price is S$111
includes taxes & fees
4 Jan - 5 Jan, 2026
Freehand Chicago
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1495)
"Nice stay"
United States
Michelle
The price is S$135
includes taxes & fees
18 Jan - 19 Jan, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2019)
"Great stay"
United States
Kramer
The price is S$111
includes taxes & fees
24 Jan - 25 Jan, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Premium bedding, down duvets, pillow-top beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1545)
"Great staff and great location. "
United States
Joe
The price is S$140
includes taxes & fees
4 Jan - 5 Jan, 2026
The Wade
Exterior
Arlo Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1913)
"Great hotel"
United States
Chris
The price is S$167
includes taxes & fees
4 Jan - 5 Jan, 2026
Arlo Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2996)
"Great place to stay"
United States
Elisha
The price is S$130
includes taxes & fees
22 Jan - 23 Jan, 2026
Aloft Chicago Mag Mile
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.
View all properties

Top Westchester Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"When I pulled up I was wholeheartedly greeted by the doorman. Upon entering the hotel it was a joyful and friendly atmosphere. The receptionist was very courteous and professional. I’ve stayed here multiply times and have been very satisfied. Will return again. One more thing, the hotel is in a great location."
Margo 3-night trip
Posted 1 day ago
The Royal Sonesta Chicago Downtown

Frequently asked questions

What's the best dog-friendly place to stay in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top hotel for people travelling with their pets, and offers a restaurant and a fitness centre for its human guests.
What's the best time of year to travel to Westchester with my pet?
When you travel with your pet, keeping tabs on the weather can help you make the trip more safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Westchester are January, November, February and December, with each month seeing an average of 13 cm of snowfall.
What is there to see and do with your pet in Westchester?
Known for its basketball, Westchester has lots to offer visitors. During your visit, enjoy visiting Wrigley Field and Michigan Avenue. When you're in the area, make time for a stop at top attractions, such as United Center and McCormick Place.

Explore a world of travel with Expedia