Chicago is one of the largest cities in the US and a major tourist magnet. The Bean at Millennium Park reflecting the city’s skyline is one of the most photographed pieces of sculpture and deserves a spot on every itinerary. When talking of Chicago, how can you forget about its famous deep-dish pizza and the Chicago-style hot dog? But when you go on a holiday, you might want something to make the vacation more fulfilling. If you’re looking for that extra element, these secluded yet modern suburban rentals that come with a pool will come to the rescue. Choose from one of these best hotels with private pool near Chicago, Illinois, when you plan your next getaway.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 23, 2025.
1. The Champagne Lodge & Luxury Suites (from USD 129)
Just 32 km (20 mi) from downtown Chicago, this luxury boutique property provides a secluded getaway away from the commotion of the city. Aiming to please, all rooms at the hotel come with a cozy fireplace and a whirlpool. Dor a truly indulgent stay, consider the Pool Suite that comes with a heated 5.2 × 2.4 m (17×8 ft) private pool featuring a massage therapy seat. The pool and the surrounding area are styled with LED mood lighting for a truly romantic experience.
And if you finally decide to leave your room, the Magnificent Mile is 39 km (24.2 mi), Drury Lane Theater is 9.6 km (6 mi), and the Cog Hill Golf Course is 4.8 km (3 mi) away.
The Champagne Lodge & Luxury Suites
2.58 km (1.7 mi) from Waterfall Glen Forest Preserve
Other accommodations with private pool near Chicago, Illinois
2. Casa Dra’eh (from USD 499)
With Meditteranean exteriors and spacious interiors, this dreamy villa is a great destination for a large group. While there are several sitting arrangements in the house, the pool will definitely serve as a crowd puller. The heated outdoor pool comes with a spacious patio and is perfect for a swim, regardless of the weather.
While Chicago is a 40 min drive away, several popular grocery stores and restaurants are just 5 minutes away, and downtown Plainfield is 4.8 km (3.1 mi) away.
Top guest reviews
Host:
the house is lovely and the hosts are excellenti highly recommend this property and hostssuch a beautiful glamorous home’ the owner’s were very kind’ responsive’ and helpfulour airbnb stay here was fantastic daniel was extremely responsive and attentivewould highly recommend hosts were extremely helpful throughout entire stay and the house is beautifulLocation:
awesome home great location great communicationRead more reviewsAmenities & Room:
a great view a cozy space and a wonderful timehuge backyard and in ground poolthe house had aa amazing kitchen and the couches were plus and comfortable
3. Gorgeous farmhouse with private pool (from USD 700)
Escape the city and head to the suburb of Lake Forest for a fun-filled getaway with family or friends. This refurbished farmhouse comes with many excellent features such as a library and a piano but its best feature has to be the large outdoor pool. Surrounded by mature trees and manicured gardens, it is the center point of this estate, with multiple sitting areas on both levels facing it.
It is easy to spend days at this house, but when you decide to venture out, Lake Forest public golf course is just a block away, while downtown Lake Forest is 1.6 km (1 mi) and the beach on the shore of Lake Michigan is 3.2 km (2 mi) away.
Top guest reviews
Host:
andy was an awesome hostandy was an incredible host thank you for your wonderful hospitalitythe owner was very helpful and responsive and he takes great care of the propertyalso andy is a great hostandy was a great host directions on where everything was at the house were crystal clearLocation:
loved the location and poolthe location was ideal for a nice walk to the shops and restaurantslocation in lake forest is fantasticthe location is also fantastic - 5 minutes from downtown lake forestit was a perfect locationCleanliness:
clean and very comfortablebeautiful comfortable clean and we hated to leaveandy’s place is so nice clean and convenient to lots of activitiesthe home was very clean and came with just about everything we neededthere was a private bath with every bedroom it was clean comfortable and roomyRead more reviewsAmenities & Room:
pool and patio was great as wellvery lived in comfortable feeling spotthe yard and the pool are gorgeouswe appreciated the well equipped kitchenthe house is perfect for a group or family gathering - wonderful kitchen and common areas
4. Modern house with an indoor pool
If you are in the mood to escape the city for some quiet time, then this modern house in Grayslake is your answer. This house with its wood-finished cabinets and a gourmet kitchen also comes with a large indoor heated pool. An additional feature of the pool is that instead of staying level, the depth goes from 1 m (3.5 ft) at the shallow end all the way to 3 m (10 ft) at the deep end.
Adjoining the pool area is an outdoor patio with benches, an outdoor kitchen, and a barbecue grill. Live the celebrity life with your private movie theater with its very own popcorn machine when you choose this house!
Grayslake, Illinois, United States
70.07 km (43.6 mi) from Waterfall Glen Forest PreserveSuperhost
Accommodates: 16
Top guest reviews
Host:
they were also super responsive throughout the weekend with any questions we hadthe host laid this home out to feel very cozy and we definitely enjoyed itlauren and zeke was very responsive and friendlyLocation:
my family enjoyed every minute at this locationconvenient location near local forest preserves for some great hikesvery nice quiet neighborhood for a relaxing timeCleanliness:
very clean and maintainedthe pool was very clean and the temperature was perfecteverything was as described and very cleanthe rooms were comfortable and cleanthe house was very clean and welcoming even our name on the board in the front foyerRead more reviewsAmenities & Room:
the pool and theater were everyone's favoritesthank you namestay we had a blast in the pool and loved the propertythere was room to spread out and we had plenty of fun things to dowe had a wonderful stay at this beautiful pool house
5. Luxurious suburban villa with a private pool (from USD 200)
Away from the packed downtown area of Chicago, this family home makes for a great getaway from Chicago or a base from which to explore the Windy City. A paved pathway from the house goes through a wooded area and leads guests to the steps of the outdoor pool. The shaded area, surrounded by manicured grass and towering trees, is fitted with outdoor furniture for large groups.
Top guest reviews
Host:
the hosts were very helpful and had a quick response time to everythingthis house was great the host was friendly and his response was quick whenever he received our textLocation:
i recommend this placeRead more reviewsAmenities & Room:
the pool and outside areas were very enjoyable though
6. Sprawling estate on the north of Chicago (from USD 1100)
A horseshoe driveway welcomes guests to this spectacular property nestled in Chicago’s affluent Highland Park. Downtown Chicago is about 40 min away by train away. Guests will have easy access to the beaches of Millard, Moraine, Park Avenue, and Rosewood for some fun under the sun.
But with the estate coming with its very own fenced-in pool, you might never make it to the beaches. The heated pool is open only during the summer months. It ranges in depth from 0.9 m (3 ft) in the shallow end to 3.65 meters (12 ft) on the diving board fitted the deep end. A paved patio area adjoining the pool as well as the house comes with multiple sitting spaces.
Top guest reviews
Host:
kailash was an outstanding hostamazing stay very thoughtful hostthe host was amazing checked on us during our stay to make sure we didn’t need anythingkailash is a wonderful host this was by far my best airbnb experiencethis place was beyond gorgeous and kailash was very helpful and responsive he even stopped by to assist usLocation:
beautiful area/ trails for walking and running nice trails close to housegreat place and perfect location and distance from navy yard and airportthe neighborhood is quiet and is in a perfect locationgreat house for families great locationfantastic location close to restaurants shopping great lakes navy base and so much moreCleanliness:
this was an amazing clean relaxing place to staybeautiful spacious and spotlessly clean home in an excellent locationhome is very clean and spaciousthe place was very clean and had all of the necessities for a few nights staythe house was wonderful just as described it was very neat and clean and had welcoming touchesRead more reviewsAmenities & Room:
with 6 bedrooms and 4 bathrooms it easily accommodated our familyfirst the good stuff:the beds were really comfortable and the furniture inside was really nice and well decoratedgorgeous stylish home plenty of room for our group of 8we were immediately impressed with the size and beautiful decor and gourmet well stocked kitchenhighly recommended clean great bbq grill great pool lots of house space beautiful property
Exploring beyond the Windy City
Chicago is a multicultural hub for finance, culture, and education but sometimes you need to take a break and retreat to the suburbs. The city is surrounded by well-planned suburbs each with its own attractions and all close to the beaches of Lake Michigan. But with these spacious properties, each with its own pool you will be happy never stepping out. Pick from one of these best hotels with private pool near Chicago, Illinois for your next trip.
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