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Find Hotels with a Pool in Highwood, IL

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Nov 10 - Nov 11
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Nov 11 - Nov 12
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Highwood hotels with a pool

A large indoor swimming pool with multiple lounge chairs and a blue chair in the center.

1. La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
3.0 star property
Deerfield
9.0 out of 10, Wonderful, (1,007 reviews)
  • cleanliness
    Dive into a refreshing retreat with an indoor pool that makes a splash in this family-friendly escape.
$88 nightly
The price is $98
Dec 6 - Dec 7
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.

2. Hyatt Regency Deerfield

Hyatt Regency Deerfield
4.0 star property
Deerfield
8.8 out of 10, Excellent, (1,335 reviews)
  • cleanliness
    Splash into serenity at this indoor pool retreat where relaxation meets refreshing luxury.
$95 nightly
The price is $108
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Deerfield
An indoor swimming pool with clear lane markings and a lifeguard station.

3. Homewood Suites by Hilton Chicago-Lincolnshire

Homewood Suites by Hilton Chicago-Lincolnshire
3.0 star property
Lincolnshire
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary offers sun loungers and cozy fireside relaxation.
$110 nightly
The price is $123
Dec 5 - Dec 6
Total with taxes and fees
Homewood Suites by Hilton Chicago-Lincolnshire
A pool area with a glass-enclosed patio, furnished seating, and a clear view of the surrounding buildings.

4. Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook
3.0 star property
Highland Park
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Luxurious indoor pool sanctuary awaits after hiking Lake Michigan's scenic trails.
$107 nightly
The price is $119
Nov 22 - Nov 23
Total with taxes and fees
Courtyard by Marriott Chicago Highland Park/Northbrook
A poolside area with lounge chairs and umbrellas, a pool, and a view of a building with balconies.

5. Courtyard by Marriott Chicago Deerfield

Courtyard by Marriott Chicago Deerfield
3.0 star property
Deerfield
8.4 out of 10, Very good, (1,005 reviews)
  • cleanliness
    Dive into aquatic bliss at this Chicago hotel's inviting indoor pool, perfect for year-round swimming near Lake Michigan.
$92 nightly
The price is $97
Nov 22 - Nov 23
Total with taxes and fees
Courtyard by Marriott Chicago Deerfield
A heated indoor pool area with a hot tub, seating, and large windows.

6. Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield
4.0 star property
Deerfield
9.0 out of 10, Wonderful, (1,371 reviews)
  • cleanliness
    Pool paradise with a side of relaxation awaits at this refreshing getaway with indoor swimming and hot tub.
$125 nightly
The price is $142
Nov 23 - Nov 24
Total with taxes and fees
Embassy Suites by Hilton Chicago North Shore Deerfield
A hotel swimming pool with two separate sections, chairs around the pool, and a sign indicating pool rules.

7. Holiday Inn Express & Suites Chicago-Deerfield/Lincolnshire by IHG

Holiday Inn Express & Suites Chicago-Deerfield/Lincolnshire by IHG
2.5 star property
Riverwoods
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Plunge into pool perfection with a warm, soothing indoor swim and bubbling hot tub after exploring Chicago's attractions.
$99 nightly
The price is $110
Dec 10 - Dec 11
Total with taxes and fees
Holiday Inn Express & Suites Chicago-Deerfield/Lincolnshire by IHG
A swimming pool with clear water, surrounded by lounge chairs and tables, large windows with a view of trees and buildings, and a ceiling with recessed lighting.

8. Hampton Inn & Suites Chicago/Lincolnshire

Hampton Inn & Suites Chicago/Lincolnshire
2.5 star property
Lincolnshire
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Splash into serenity at this hotel with an indoor pool that's clean, refreshing, and always the perfect temperature.
$101 nightly
The price is $113
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn & Suites Chicago/Lincolnshire
An indoor swimming pool with clear windows, chairs, and potted plants.

9. Hilton Garden Inn Lake Forest Mettawa

Hilton Garden Inn Lake Forest Mettawa
3.0 star property
Lake Forest
9.0 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Dive into poolside bliss at this lakeside sanctuary where swimming meets year-round comfort.
$117 nightly
The price is $130
Nov 20 - Nov 21
Total with taxes and fees
Hilton Garden Inn Lake Forest Mettawa
A swimming pool with lounge chairs and umbrellas, surrounded by a tiled deck and a white tent structure.

10. Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield
4.0 star property
Deerfield
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Splash into summer at this upscale hotel where sun loungers surround a seasonal outdoor pool and relaxation awaits.
$125 nightly
The price is $141
Nov 22 - Nov 23
Total with taxes and fees
Chicago Marriott Suites Deerfield
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.
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Choose what matters most at hotels with a pool in Highwood

Breakfast included
Hot tub

Top Highwood Hotel Reviews

A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

Hyatt Regency Deerfield
Deerfield

10/10 Excellent

I gotta say I would definitely recommend this Hotel and will book with them again if Im around chicago again. The room looks clean and VERY spacious with affordable price. It has heated pool and a gym. Also I paid extra to include the breakfast buffet during my visit which was worth it.
United States
Mohammaderfan
Reviewed January 9, 2026
Hyatt Regency Deerfield

Frequently Asked Questions

What are some accommodations with pools in Highwood?

Hyatt Regency O'Hare Chicago: Hotel located near Donald E. Stephens Convention Center. Offers an indoor pool, an outdoor pool, and a snack bar/deli. Marriott Chicago O'Hare: Hotel, 5-minute walk from Donald E. Stephens Convention Center. Offers 3 restaurants, an indoor pool, and complimentary wireless internet access. Loews Chicago O'Hare Hotel: Hotel, 3-minute walk from Donald E. Stephens Convention Center. Features buffet, an indoor pool, and a 24-hour fitness center. Hilton Chicago O'Hare Airport: Features a snack bar/deli, an indoor pool, and free self parking. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel, 6-minute walk from Woodfield Mall. Provides complimentary wired internet access, an indoor pool, and free self parking.

What is there to see and do in Highwood?

Explore places like Six Flags Great America while you're in the area. Enjoy a stroll along the shore at Rosewood Beach and Independence Grove Beach.

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

You may want to consider a place to stay that has an outdoor pool if you plan to visit Highwood in the warmest months of July, August, or September when the average temperature is 69°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 temperature is 30°F.

What's the best way to travel around Highwood?

Knowing the transportation options in Highwood can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Highwood Station or Highland Park Fort Sheridan Station. Highwood might not have many public transit options to choose from so consider a car rental to maximize your time.

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