Skip to content Set on Lake Michigan in Illinois, Chicago is among the largest cities in the U.S. and is filled with many amazing attractions, including stunning works of architecture, museums, Millennium Park, Navy Pier, etc. If you are looking for an accommodation for your next trip to Chicago that includes a private pool, you’re in the right place. We have made a list of all the hotels, apartments, and holiday homes that offer a pool as an amenity. Check it out!
This Chicago hotel for adults offers romantic pool suites (CL Swimming Pool Suite), as well as whirlpool suites, all with great amenities for as low as $120 USD.
All luxurious suites come with a steam shower, rain shower, fireplace, flat-screen TV, and other usual amenities.
Their package plans include dinner, in-room massage services, golf, and much more.
Click here to read our full guide to The Champagne Lodge & Luxury Suite
Yet another Sybaris hotel on our list, and it’s just as amazing as the others. It offers amazing whirlpool and pool suites for a perfect romantic getaway in Chicago.
All suites feature a relaxing hot tub in room, a fireplace, and a love swing (available only on this location).
Pool suites also boast a private pool with a tropical waterfall, a steamroom, and massage chairs. For more hotels for adults like this, click here.
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By Cupid from Hotels With Hot Tub in Room . Club
This luxurious and romantic hotel in Chicago promises to deliver the perfect romantic experience to couples. It features whirlpool and swimming pool suites of everybody’s dreams.
All cozy suites include a fireplace, a hot tub, a TV, and complimentary toiletries and spa robes. Some also boast a private pool.
There’s also a convenience area with a microwave, a tea/coffee maker, and a refrigerator.
Sybaris was voted the best romantic getaway in the US and we have to say: their adult-only suites are made for honeymoons, anniversary celebrations, and any other special occasion you wish to celebrate with your SO.
All suites include a spacious whirlpool tub in room, a fireplace, a misting steamroom, and relaxing massage chairs.
Some suites also come with a spacious private pool with a slide.
Nestled in the heart of Chicago, near to all major Chicago attractions, this luxury holiday home promises an unforgettable stay.
The house features 3 bedrooms, 1 bathroom, a full kitchen, separate dining area, a living room, and free parking.
The spacious patio comes with a private seasonal pool, 2 furnished decks, fire pit, grill, cooler, and enough space to host wedding parties or other celebrations.
This lovely vacation rental is set in the suburbs of Chicago, peaceful yet near all famed points of interest.
This home offers 4 bedrooms, 2.5 bathrooms, a living room with a fireplace, a full kitchen, and a separate dining area. Private and public parking is available.
The house also boasts a spacious backyard featuring a seasonal heated pool, a gazebo, and a grill with an outdoor dining table.
This gorgeous historic colonial home features 4 bedrooms, 2.5 bathrooms, a kitchen, a dining area, and a cozy living room with a fireplace and a piano.
The property also boasts a beautiful backyard with an above-ground pool, an outdoor seating area, and a garden.
If you wish to explore the area, it’s only 20 mins to downtown Chicago, 5 mins to Lake Michigan beaches, and 30 mins to Six Flags Great America.
Set in adjacent Indiana, the Blue Butterfly II is about 45-minutes drive from Chicago. The property is also steps from beaches of Lake Michigan and a number of restaurants.
This pet-friendly, 2-floor home comes with 5 bedrooms, 2 updated bathrooms, a full kitchen, a laundry room, a living room, and private parking.
The spacious backyard offers a BBQ, a seating area, and an above-ground pool.
This charming and spacious ranch home is set in upscale Glenview neighborhood. It’s steps from Wagner Farm, a park, trails, many bars, restaurants, and shops; and offers easy access to downtown Chicago.
It features 4 bedrooms, 2 bathrooms, a full kitchen, a dining area, cozy living room, and a large patio. 2-car parking is also available.
The patio includes a private pool, fire pit, and outdoor furniture.
If you’re looking for a different type of romantic hotels in Chicago for a couple’s weekend getaway, here are some suggestions!
Did you know that there are users who have stayed in these hotels and have uploaded their real videos to Youtube? We have collected and put them here so you can see more closely what these rooms and suites are like inside. We hope you like it and don’t forget to share it with your SO!
If your budget allows, Sybaris is a fantastic option for you. Because has trully high-class suites. However, if you're working with a more limited budget, there are other excellent choices that offer great value for your money. For example, consider The Champagne Lodge & Luxury Suites in Willowbrook – it's a wonderful alternative that won't break the bank.
Sybaris and The Champagne Lodge are the most romantic and luxurious hotels with a pool in room in Chicago.
Without a doubt, anyone who can afford to spend over $500 USD for the Sybaris Paradise Pool Suite could be considered a celebrity in their own right. It's highly likely that celebrities looking to celebrate special nights will choose the most luxurious, romantic, and expensive suites in Chicago for their unforgettable experiences.
The Champagne Lodge and Luxury Suites is similar to Sybaris, according to many guests.
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