Title: Book the Best Hotels with POOL in Westchester in 2025 | Expedia.ca

  

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# Find Hotels with a Pool in Westchester, IL from CA $152

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## Check availability on Westchester Hotels with a Pool

Tonight

[Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7758&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Westchester Hotels with a Pool

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Wade

Downtown Chicago

8.4/10

Very good

(1397)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adam

CA $155

CA $182 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Palmer House a Hilton Hotel

Downtown Chicago

8.4/10

Very good

(2045)

"Great place to stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ron

CA $147

CA $208 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

![Indoor pool, open 5:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/a8da386d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### voco Chicago Downtown - Riverwalk by IHG

Downtown Chicago

8.8/10

Excellent

(3280)

"Great location, staff very attentive. Hotel was clean and close to riverwalk and downtown "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rocio

CA $182

CA $213 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information)

![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aloft Chicago Mag Mile

Downtown Chicago

8.6/10

Excellent

(2876)

"Had a great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josh

CA $151

CA $177 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/d3f07aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Royal Sonesta Chicago River North

Downtown Chicago

9.2/10

Wonderful

(2206)

"Great stay. Great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

CA $165

CA $238 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/fe59f9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

8.8/10

Excellent

(1696)

"Excellent hotel in a wonderful location of Chicago!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amy

CA $130

CA $152 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/1ac4706c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2496x3y3-f9e98aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

9.0/10

Wonderful

(1034)

"Great Hotel!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wendy

CA $178

CA $250 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information)

![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/f5341c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/0405e59a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/d70c748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Radisson Blu Aqua Hotel Chicago

Downtown Chicago

8.6/10

Excellent

(1738)

"Excellent Location and beautiful views from the rooms!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christina

CA $196

CA $266 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Chicago Downtown/Magnificent Mile

Downtown Chicago

8.4/10

Very good

(4118)

"This hotel had a great location to shopping and several enjoyable restaurants."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

laura

CA $162

CA $190 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

8.6/10

Excellent

(5168)

"We enjoyed our stay, great location for walking around downtown. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tami

CA $177

CA $208 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12&regionId=7758&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Westchester Hotel Reviews

![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"i have been visiting chicago frequently over the last few months and this hotel thus far has exceeded any hotel stay that ive had. the staff was amazing and the location and room was great for the money spent. i will return "

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg)

### The Whitehall Hotel, BW Premier Collection

10/10 Excellent

"Staff was very nice and the hotel is near everything "

[](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg)

### Warwick Allerton - Chicago

10/10 Excellent

"Computers need updates. Staff great."

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg)

### Congress Plaza Hotel

10/10 Excellent

"Great"

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"The only negative experience was seeing the Disgraceful Trump Tower across the street. "

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Pendry Chicago](//images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg)

### Pendry Chicago

10/10 Excellent

"We loved the Pendry!"

[](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information)

![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg)

### Hotel Felix River North/Magnificent Mile

10/10 Excellent

"Staff and location"

[](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"We enjoyed our stay, great location for walking around downtown. "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Crowne Plaza Chicago West Loop by IHG](//images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg)

### Crowne Plaza Chicago West Loop by IHG

10/10 Excellent

"Staff was friendly upon check in and the premise was very clean."

[](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information)

## Frequently asked questions

### What are some accommodations with pools in Westchester?

> [Congress Plaza Hotel](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen televisions. [Hilton Chicago/Magnificent Mile Suites](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Provides complimentary wired internet access, an indoor pool, and LCD televisions. [Freehand Chicago](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information): Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access. [CitizenM Chicago Downtown](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information): Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool, and a sauna. [Embassy Suites by Hilton Chicago Downtown River North](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information): Hotel, 4-minute walk from State Street. Provides 2 restaurants, an indoor pool, and a health club.

### What is there to see and do in Westchester?

> While you're in the area, consider exploring places like Wrigley Field, Michigan Avenue, and Navy Pier. Take a walk along the waterfront at Oak Street Beach and North Avenue Beach. The restaurants and shopping are just some of the things to enjoy while you're in the area.

### When is the best time to book a hotel with a pool in Westchester?

> You may want to consider a place to stay that has an outdoor pool if you're planning to visit Westchester in the hottest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 31°F.

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