TOP Hotels with Pool in Highwood, IL for 2026

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Our top choices for Highwood hotels with a pool

A heated indoor pool area with a hot tub, seating, and large windows.

A multi-story building with a sign reading "Embassy Suites."

A spacious lobby with a fireplace, comfortable seating, and a high ceiling with multiple balconies.

A bar area with wooden chairs and tables, a counter with bottles and glasses, and a wooden ceiling structure.

1. Embassy Suites by Hilton Chicago North Shore Deerfield

Deerfield

Pool paradise with a side of relaxation awaits at this refreshing getaway with indoor swimming and hot tub.

฿4,106

฿4,680 total

includes taxes & fees

18 Oct - 19 Oct

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

A hotel room with a large bed, a desk, a chair, a television, and a sofa.

A spacious dining area with multiple tables and chairs, large windows, and a central decorative plant.

A spacious lobby with a reception desk, seating area, and a large glass door entrance.

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

Deerfield

Dive into a refreshing retreat with an indoor pool that makes a splash in this family-friendly escape.

฿2,828

฿3,138 total

includes taxes & fees

18 Oct - 19 Oct

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating "Lifeguard on Duty".

An outdoor patio area with a stone fire pit, seating, and a barbecue grill.

A spacious lobby with a high ceiling, stone pillars, and a central seating area with blue and brown chairs.

A hotel entrance with a sign reading "Homewood Suites Hilton".

3. Homewood Suites by Hilton Chicago-Lincolnshire

Lincolnshire

Refreshing indoor pool sanctuary offers sun loungers and cosy fireside relaxation.

฿3,699

฿4,143 total

includes taxes & fees

1 Nov - 2 Nov

A hotel swimming pool with two separate sections, chairs around the pool, and a sign indicating pool rules.

A compact hotel room with a kitchenette, a desk with a lamp, a chair, and a sofa.

A compact kitchen with a microwave, coffee maker, and a small refrigerator.

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

Riverwoods

Plunge into pool perfection with a warm, soothing indoor swim and bubbling hot tub after exploring Chicago's attractions.

฿3,602

฿3,998 total

includes taxes & fees

2 Nov - 3 Nov

An indoor swimming pool with clear windows, chairs, and potted plants.

A spacious lobby with a fireplace, comfortable seating, and a large TV screen.

A spacious lobby with a central reception area, a shop, and potted plants.

An outdoor patio area with brick flooring, outdoor seating with cushions, and umbrellas providing shade.

5. Hilton Garden Inn Lake Forest Mettawa

Lake Forest

Dive into poolside bliss at this lakeside sanctuary where swimming meets year-round comfort.

฿4,382

฿4,863 total

includes taxes & fees

23 Oct - 24 Oct

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

An outdoor seating area with sofas, tables, and chairs, surrounded by greenery and a building with an arched entrance.

A spacious dining area with multiple tables, chairs, and a central fireplace.

A modern bathroom with a large mirror, a sink, and a shower area.

6. Hyatt Regency Deerfield

Deerfield

Splash into serenity at this indoor pool retreat where relaxation meets refreshing luxury.

฿4,256

฿4,809 total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel kitchen with a buffet area, a dining table with chairs, and a coffee station.

An outdoor patio with a fire pit, wicker furniture, and a pool in the background.

A modern living room with a fireplace, leather armchairs, a round coffee table, and a sofa.

7. Residence Inn By Marriott Chicago Deerfield

Deerfield

Splash into summer at this hotel's seasonal outdoor pool, complete with sun loungers and poolside firepit.

฿5,017

฿5,668 total

includes taxes & fees

1 Nov - 2 Nov

A pool area with a glass-enclosed patio, furnished seating, and a clear view of the surrounding buildings.

A modern living room with a fireplace, comfortable seating, and large windows.

A modern bar area with a bar counter, seating, and a menu board.

A modern outdoor seating area with a fire pit, wicker furniture, and a building with balconies in the background.

8. Courtyard by Marriott Chicago Highland Park/Northbrook

Highland Park

Luxurious indoor pool sanctuary awaits after hiking Lake Michigan's scenic trails.

฿3,606

฿4,002 total

includes taxes & fees

1 Nov - 2 Nov

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Choose what matters most at hotels with a pool in Highwood

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top Highwood Hotel Reviews

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

10/10 Excellent

"Great stay convenient to the airport."

Embassy Suites by Hilton Chicago O'Hare Rosemont

10/10 Excellent

"Breakfast was excellent.."

Hyatt Regency Schaumburg Chicago

10/10 Excellent

"Excellent staff! Front desk, bar, breakfast, housekeeping, every single person at this hotel is fantastic. Great location for city or suburbs."

Comfort Suites Chicago O'Hare Airport

10/10 Excellent

"Reasonably good condition apart from some scuffed doors near the elevators Large suites and clean"

DoubleTree by Hilton Chicago - North Shore Conference Center

8/10 Good

"The king size bed and pillows were extremely comfortable"

Quality Inn O'Hare Airport

10/10 Excellent

"If you have door issues. Lift up on the handle instead of down."

Frequently asked questions

What are some accommodation options 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 centre. 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 high-speed (wired) Internet access, an indoor pool and free self parking.

What is there to see and do in Highwood?

Explore places such as 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 with an outdoor swimming pool if you'll be visiting Highwood in the warmest months of July, August or September, when the average temperature is 21°C. Accommodation with an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is -1°C.

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 explore the surrounding area, hop aboard a train at Highwood Station or Highland Park Fort Sheridan Station. Highwood might not have very many public transport options to choose from, so consider a car rental to maximise your time.

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Check availability on Highwood Hotels with Pool

Our top choices for Highwood hotels with a pool

1. Embassy Suites by Hilton Chicago North Shore Deerfield

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

3. Homewood Suites by Hilton Chicago-Lincolnshire