Photo by Meghan hernandez

Hotels with Pool & Resorts in Highland Park from AU$187

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Best Highland Park Hotels with Pool

Courtyard by Marriott Chicago Highland Park/Northbrook

3.0 star property
9.0 out of 10, Wonderful, (862)
"Beyond exceptional. Very clean and so much included. I’m happy with my choice to stay at Courtyard!"
The price is AU$187
includes taxes & fees
8 Dec - 9 Dec
Courtyard by Marriott Chicago Highland Park/Northbrook
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.
Don't see what you're looking for?
See all available properties in Highland Park
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What are some accommodation options with pools in Highland Park?
Thompson Chicago, by Hyatt: Hotel located near Donald E. Stephens Convention Center. Features an indoor pool, an outdoor pool and a snack bar/deli. Hilton Chicago O’Hare Airport: Hotel, 7-minute walk from Allstate Arena. Offers complimentary wireless Internet access, an indoor pool and Smart televisions. Chicago Getaway Hostel: Hotel, 4-minute walk from Donald E. Stephens Convention Center. Offers 3 restaurants, an indoor pool and complimentary wireless Internet access. Marriott Chicago O’Hare: Hotel, 3-minute walk from Allstate Arena. Provides a snack bar/deli, an indoor pool and buffet. Holiday Inn Chicago O’Hare – Rosemont, an IHG Hotel: Hotel, 2-minute walk from State Street. Features 2 restaurants, a seasonal outdoor pool and a rooftop terrace.
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 Ravinia Park and Chicago Botanic Garden. 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.