A calm lake with ducks, autumn trees, and a grassy park area.

Westchester Hotel Guide - Hotels with Pool in Westchester, Chicago

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Check availability on Westchester Hotels with Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Westchester hotels with a pool

A poolside area with lounge chairs and a swimming pool.
A modern building with a flat roof, large windows, and a reflection in the water.
A gym with treadmills, elliptical machines, and weight stations.
A banquet hall with round tables, chairs, and chandeliers.

1. Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago
Oak Brook
  • Discover serene luxury at this lakeside hotel where an indoor pool sanctuary awaits, surrounded by lush forests and hiking trails.
€156
includes taxes & fees
1 Nov - 2 Nov
Hyatt Lodge Oak Brook Chicago
An indoor swimming pool with lounge chairs and a glass ceiling.
A spacious lobby with a marble floor, modern lighting fixtures, a seating area with sofas and chairs, and a visible kitchen area in the background.
Room
A glass-enclosed patio with outdoor seating and a view of the surrounding buildings.

2. Chicago Club Inn & Suites

Chicago Club Inn & Suites
Westmont
  • Luxurious indoor pool sanctuary provides year-round aquatic escape at this peaceful suburban Chicago retreat.
€63
includes taxes & fees
3 Nov - 4 Nov
Chicago Club Inn & Suites
An indoor swimming pool with clear water, sunlit by large windows, surrounded by lounge chairs and a lifeguard stand.
A modern bar area with a central island, bar stools, shelves with bottles, and pendant lighting.
A modern kitchen with a dishwasher, microwave, and built-in oven. There is a dining area with a large island and bar stools. A flat-screen TV is mounted on the wall.
A modern kitchen with a central island, stainless steel appliances, and a large window.

3. Hyatt House Chicago Oak Brook

Hyatt House Chicago Oak Brook
Oak Brook
  • Splash into family-friendly relaxation with this hotel's refreshing indoor pool oasis near Oakbrook Centre Mall.
€181
includes taxes & fees
30 Oct - 31 Oct
Hyatt House Chicago Oak Brook
A golf course with a swimming pool, lounge area, and a pond.
A large hotel with a central courtyard, a lake, and a bridge.
A room with a large window, a bed, and a sofa.
A spacious, modern interior with large windows offering views of a golf course and a lake.

4. Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center
Oak Brook
  • Dive into a poolside oasis with year-round swimming at this upscale golf resort.
€135
includes taxes & fees
1 Nov - 2 Nov
Hilton Chicago/Oak Brook Hills Resort & Conference Center
An indoor swimming pool with clear blue water, white walls, and blue accents.
A modern bathroom with a granite countertop, a large mirror, and a shower area with a glass door.
A modern hotel room with a large bed, a desk, and a seating area.
A reception area with a sign for Rodeway Inn, a reception desk, two blue armchairs, a small table with a plant, and a carpet with the hotel name.

5. Rodeway Inn Lyons - La Grange

Rodeway Inn Lyons - La Grange
Lyons
  • Swim year-round in a tranquil indoor pool at this convenient train station motel.
€85
includes taxes & fees
26 Oct - 27 Oct
Rodeway Inn Lyons - La Grange
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, under a high ceiling with visible structural beams.
A hotel lobby with seating areas, a fireplace, a bar, and a dining area.
A multi-story hotel with a prominent entrance and a parking lot.
A lobby with seating areas, a reception desk, and a decorative wall.

6. Hyatt Place Chicago/Lombard/Oak Brook

Hyatt Place Chicago/Lombard/Oak Brook
Lombard
  • Splash into relaxation at this indoor pool retreat with a well-maintained fitness centre nearby.
€105
includes taxes & fees
25 Oct - 26 Oct
Hyatt Place Chicago/Lombard/Oak Brook
A large indoor swimming pool with clear blue water, surrounded by wooden chairs and tables, and walls with a patterned tile design.
A modern hotel room with a large bed, a desk, a chair, and a TV.
A spacious lobby with a central seating area, large wooden columns, and potted plants.
A multi-story hotel with a prominent "WESTIN" sign on the top.

7. The Westin Chicago Lombard

The Westin Chicago Lombard
Lombard
  • Serene indoor swimming sanctuary with temperature-controlled waters and plush poolside loungers for year-round aquatic relaxation.
€129
includes taxes & fees
18 Oct - 19 Oct
The Westin Chicago Lombard
An indoor swimming pool with a clear water surface, a metal ladder, and a no diving sign.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A living room with two sofas, a fireplace, a TV, and a bookshelf.
A modern restaurant with wooden chairs, a long counter, and a buffet area.

8. Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Bensenville
  • Relax and revive with year-round swims at this O'Hare hotel's indoor pool and hot tub retreat.
€98
includes taxes & fees
25 Oct - 26 Oct
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
An indoor swimming pool with clear water, surrounded by lounge chairs and a stone wall.
A hotel room with a bed, desk, chair, TV, and a large window with a city view.
A reception area with three wooden reception desks, a glass wall on the left, and a colorful artwork on the right.
A covered outdoor seating area with wicker furniture and a view of the street.

9. Holiday Inn Chicago Oakbrook by IHG

Holiday Inn Chicago Oakbrook by IHG
Oakbrook Terrace
  • Splash into year-round fun with an indoor pool that's perfect for both business and leisure travellers.
€99
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Chicago Oakbrook by IHG
An indoor swimming pool with clear water, surrounded by windows offering views of the parking lot and trees.
A hotel reception area with a modern design, including a reception desk, a digital display, and seating arrangements.
A modern bathroom with a large mirror, a sink, a toilet, and a glass shower enclosure.
A Hampton Inn & Suites building with a modern design, featuring a brick facade, large windows, and a covered entrance area.

10. Hampton Inn & Suites Chicago-Burr Ridge

Hampton Inn & Suites Chicago-Burr Ridge
Burr Ridge
  • Dip into year-round refreshment at this indoor pool sanctuary near SeatGeek Stadium, where comfort meets convenience.
€123
includes taxes & fees
31 Oct - 1 Nov
Hampton Inn & Suites Chicago-Burr Ridge
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Choose what matters most at hotels with a pool in Westchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Westchester Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"N:a"
Julie 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

8/10 Good
"Solid 4 out of 5 star hotel. Great location and helpful staff. No room service keeps it from 5 star territory."
Eric 3-night trip
Posted 7 hours ago
Hilton Chicago
The Wade

The Wade

10/10 Excellent
"Everything was super clean They made the bed everyday and made sure we had fresh towels. Every time we went into the elevator the staff was very friendly and even asked how our day was going or did we slept well"
Clarissa 4-night trip
Posted 10 hours ago
The Wade
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Clean sensible hotel. Can’t beat location."
Michael 1-night trip
Posted 11 hours ago
InterContinental Chicago Magnificent Mile by IHG
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

8/10 Good
"Nice room and great location…need a restaurant and real bar-bar is sort of open…would like to see it after they really rebrand everything"
Matthew 1-night trip
Posted 12 hours ago
Sports Illustrated Resorts Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"The room was spacious and the bed was very comfortable. The check in was easy and they gave us a voucher for a drink in the lounge bar. We had a very nice stay. Great location, the river walk is with in walking distance."
Guadalupe 1-night trip
Posted 12 hours ago
Hyatt Regency Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Spacious room. Great location."
Keith 4-night trip
Posted 2 days ago
The Royal Sonesta Chicago Downtown

Frequently asked questions

What are some accommodation options with pools in Westchester?
River Hotel: Hotel, 2-minute walk from Grant Park. Features 2 restaurants, an indoor pool and a health club. Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a sauna. The Chicago Hotel Collection Ambassador Gold Coast: Hotel, 8-minute walk from Lake Michigan. Offers complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre.
What is there to see and do in Westchester?
While you're in the area, consider exploring places such as Wrigley Field, Soldier Field 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 plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation 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 -1°C.