Photo by Meghan hernandez

Highland Park Hotel Guide - Hotels with Pool in Highland Park, Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Highland Park Hotels with Pool

Tonight
4 Aug - 5 Aug
Tomorrow
5 Aug - 6 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Highland Park Hotels with Pool

Courtyard by Marriott Chicago Highland Park/Northbrook
Relax by the pool surrounded by a garden view.

Courtyard by Marriott Chicago Highland Park/Northbrook

3.0 star property
9.0 out of 10, Wonderful, (956)
"Excellent stay"
The price is €111
includes taxes & fees
17 Aug - 18 Aug
Courtyard by Marriott Chicago Highland Park/Northbrook
Viceroy Chicago
Relax by the rooftop pool with a stunning city view.

Viceroy Chicago

4.5 star property
9.4 out of 10, Exceptional, (1071)
"We had a great stay!"
The price is €288
includes taxes & fees
1 Sept - 2 Sept
Viceroy Chicago
Level Chicago – Old Town
Relax by the rooftop pool with a view of the city.

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (334)
"A lot of good food options walkable distance. "
Level Chicago – Old Town
The Robey, Chicago, a Member of Design Hotels
Relax by the rooftop pool with a stunning city view, surrounded by lounge chairs and umbrellas.

The Robey, Chicago, a Member of Design Hotels

3.5 star property
9.2 out of 10, Wonderful, (951)
"nice stay."
The price is €185
includes taxes & fees
1 Sept - 2 Sept
The Robey, Chicago, a Member of Design Hotels
The Hotel at Midtown
Experience the city skyline from the comfort of our outdoor pool area, surrounded by lounge seating and umbrellas.

The Hotel at Midtown

4.0 star property
9.0 out of 10, Wonderful, (794)
"Beautiful hotel with great athletic amenities, food, and perfect for a stop in Chicago."
The Hotel at Midtown
Hilton Garden Inn Chicago North Shore/Evanston
Swimmers can enjoy a refreshing dip in the rectangular pool surrounded by a tiled floor.

Hilton Garden Inn Chicago North Shore/Evanston

3.5 star property
8.8 out of 10, Excellent, (1001)
"The hotel was clean and very convenient to the local shopping and dining district. I really enjoyed my stay."
The price is €150
includes taxes & fees
2 Sept - 3 Sept
Hilton Garden Inn Chicago North Shore/Evanston
DoubleTree by Hilton Chicago - North Shore Conference Center
Enjoy a classic dining experience with a variety of seating options and a selection of beverages.

DoubleTree by Hilton Chicago - North Shore Conference Center

4.0 star property
8.6 out of 10, Excellent, (1013)
"Great place "
The price is €133
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Chicago - North Shore Conference Center
Residence Inn by Marriott Chicago Wilmette/Skokie
Relax and socialize by the pool, surrounded by comfortable lounge chairs and tables.

Residence Inn by Marriott Chicago Wilmette/Skokie

3.0 star property
9.2 out of 10, Wonderful, (669)
"Kitchen is amazing place for our family to stay."
The price is €166
includes taxes & fees
17 Aug - 18 Aug
Residence Inn by Marriott Chicago Wilmette/Skokie
Holiday Inn Chicago North Shore by IHG
Relax by the pool surrounded by lounge chairs and a glass barrier offering a view of the hotel's upper levels.

Holiday Inn Chicago North Shore by IHG

3.0 star property
7.4 out of 10, Good, (1321)
"A clean and comfortable stay for a very reasonable price. "
The price is €128
includes taxes & fees
25 Aug - 26 Aug
Holiday Inn Chicago North Shore by IHG
Sheraton Chicago Northbrook Hotel
Swimmers can enjoy a rectangular pool with clear lanes and a shallow end, surrounded by lounge chairs and a table for relaxation.

Sheraton Chicago Northbrook Hotel

3.5 star property
8.6 out of 10, Excellent, (1001)
"Nice property and convenient hotel to Winnetka. "
The price is €154
includes taxes & fees
10 Aug - 11 Aug
Sheraton Chicago Northbrook Hotel
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.

Top Highland Park Hotel Reviews

Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

10/10 Excellent
"Overall it was a great stay with great cleanliness and nice sized rooms. Limited parking especially in the rear and was very weedy back there."
Nathan 3-night trip
Posted 19 hours ago
Hyatt Place Chicago/O'Hare Airport

Frequently asked questions

What are some accommodation options with pools in Highland Park?
Hilton Chicago O'Hare Airport: Hotel, 4-minute walk from Donald E. Stephens Convention Center. Provides 3 restaurants, an indoor pool and complimentary wireless Internet access. 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. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG: Hotel, 3-minute walk from Allstate Arena. Provides a snack bar/deli, an indoor pool and buffet. Claridge House: Hotel, 2-minute walk from State Street. Offers a rooftop terrace, a seasonal outdoor pool and complimentary bicycles. Marriott Chicago O'Hare: Hotel located near Donald E. Stephens Convention Center. Features 2 restaurants, an indoor pool and a sauna.
What is there to see and do in Highland Park?
Explore places such as Lake Michigan while you're in Highland Park. Spend some time experiencing the great outdoors at Chicago Botanic Garden and Moraine Park. The gardens, 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 Highland Park?
You may want to consider a place to stay that offers an outdoor pool if you plan to visit Highland Park in the hottest 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 visit during the coldest months of January, February or December, when the average temperature is -1°C.
What's the best way to travel around Highland Park?
Knowing the transportation options in Highland Park can help you enjoy the area beyond your hotel pool. If you'd like to explore more of the area, hop on a train from Highland Park Station, Highland Park Ravinia Station or Highland Park Ravinia Park Station. Highland Park might not have many public transport options to choose from, so consider renting a car to explore more.