Holiday rentals with a hot tub in Chicago

4.93 out of 5 average rating, 102 reviews

A rooftop hot tub is illuminated with soft blue lights, offering a view of the Chicago skyline at night. The sparkling water reflects surrounding city lights, creating a relaxing environment for unwinding after a day of exploration.

Condo in Wicker Park

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck

Look no further for your luxury Chicago getaway. In the heart of Wicker Park, our condo is just blocks away from fantastic restaurants, shops, and nightlife on Division and Milwaukee, and just a block from the Division El Stop - Be downtown in just 10 minutes! The unit comes with a fully equipped kitchen, bathroom amenities, smart TVs in each room, high-speed internet and direct roof-top access. Relax after a long day of exploring Chicago in the rooftop hot tub overlooking the Chicago skyline.

Hot tubOutdoor spacesIndoor spaces

4.98 out of 5 average rating, 81 reviews

The modern living area features a spacious sectional sofa in light gray, inviting relaxation. A large abstract artwork adorns the wall, while the kitchen bar showcases yellow stools. Bright lighting from pendant fixtures enhances the open layout, with hardwood floors adding warmth.

Condo in West Town

Superiorhaus Noble Square Sleeps 16 HotTub/RecRoom

Welcome to SuperiorHaus, an exquisitely designed condo in Chicago’s West Town neighborhood! This contemporary home offers a blend of luxury and comfort. Enjoy spacious living spaces curated with a keen eye for detail, a fully equipped gourmet kitchen, open dining area, vibrant bathrooms, a rec room w/ billiards(8ft), shuffleboard, darts, & a private roof deck with a hot tub to unwind from your adventures. With easy access to downtown attractions, this condo is your gateway to the best of Chicago

Outdoor spacesBathroomTV

4.93 out of 5 average rating, 30 reviews

Home in South Side

Historic Bronzeville Wellness Retreat/Hot tub

Stay in a landmark 175 yr old Bronzeville Brownstone reimagined by a Chicago nurse as a serene retreat—with hot tub under string lights, Sauna, exercise equipment, hammock swing, Blackstone grill, fire pit and an outdoor bar. Minutes to McCormick Place, Soldier Field, Museum Campus, White Sox Rate Field, 31st Street Beach-2 miles from Obama Center.. A quick 15 minute train ride from downtown, train station 2 blocks away. Walking distance to cafes, free street parking in a quiet neighborhood.

BathroomOutdoor spacesBackyard

4.92 out of 5 average rating, 36 reviews

Apartment in South Side

Modern Soul Retreat: 3BR in Bronzeville/HydePark

Experience a modern sanctuary where design meets history in the heart of Chicago’s legendary Bronzeville. This spacious 3-bd, 2-ba flat blends art, minimalist comfort, and cultural warmth. Steps from Hyde Park, Lake Michigan, and local cafes, the space invites you to unwind, reflect, and reconnect with the soul of the South Side. Featuring curated decor, luxury finishes, and a nod to Bronzeville’s Soulful Metropolis legacy, this home offers a one-of-a-kind stay—equal parts style and heritage.

BathroomKitchenWi-Fi

4.96 out of 5 average rating, 188 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

*Due to AirBnB new changes in fee disclosure, 15.5% of the daily rate you see goes to Airbnb* 1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (2 Queens) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. A parking space in the rear allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions. NO CHORES!

Outdoor spacesBathroomLayout

4.92 out of 5 average rating, 288 reviews

A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

Condo in Little Italy

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

BathroomOutdoor spacesSolo travel

4.96 out of 5 average rating, 312 reviews

A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.

Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

There's no other place like it in Chicago. A converted 1900's warehouse in the heart of Wicker Park - Once a Prohibition-era distillery, then a spring factory, and finally reimagined as a one-of-a-kind designer loft. Features soaring 14-foot timber ceilings, exposed brick, and a level of finish that earned a national kitchen award and a feature in TimeOut's "Best in Chicago". The kitchen is massive. The bathrooms are luxurious. Plus, Chicago's best neighborhood is right outside the door.

Outdoor spacesHot tubSleep quality

4.87 out of 5 average rating, 114 reviews

A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.

Home in Lake View

Entire house in Lakeview with yard and garage

Enjoy the luxury and privacy of a house all to yourself in Chicago's trendiest neighborhood. Very well maintained and furnished since this serves as my primary residence that I make available on Airbnb when I’m out of town. Around the corner there is a 7-Eleven and within a 10 minute walk you’ll find Target, Starbucks, Gym, Theaters, Restaurants, Bars, and much more. You can also easily walk to Wrigleyville, Boystown, or the train station which can take you downtown in under 20 minutes.

BathroomHot tubParks

4.98 out of 5 average rating, 330 reviews

An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.

Condo in Logan Square

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

Outdoor spacesHot tubKitchen

4.88 out of 5 average rating, 401 reviews

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Chicago

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets are Allowed!

Hot tubOutdoor spacesCheckout

Apartment in Downtown Chicago

Level River North | Deluxe One Bedroom Suite

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

Hot tubBathroomLaundry

4.79 out of 5 average rating, 165 reviews

4.96 out of 5 average rating, 187 reviews

Condo in West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

Experience the best of Chicago from this centrally located retreat just minutes from Downtown, top restaurants, shopping, and iconic attractions. Relax in a spa bathroom with a jetted tub and rain shower, cozy up by the fireplace, and enjoy a fully equipped kitchen. A king bedroom and queen Murphy bed comfortably accommodate up to 4 guests. Finish your evenings on the private patio gathered around the fire table.

Outdoor spacesHot tubAir conditioning

Popular amenities for Chicago hot tub accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a hot tub

4.92 out of 5 average rating, 65 reviews

Home in Wrigleyville

*New* Luxury Wrigley Penthouse, Free Parking

BathroomAccuracyComfort

5.0 out of 5 average rating, 4 reviews

Home in Northbrook

Northbrook Haven - Hot Tub/Poker Table

ComfortHospitalityAmenities

5.0 out of 5 average rating, 10 reviews

Home in South Side

Sunny 4BR Home with Garage Parking

QuietAccuracyCleanliness

4.82 out of 5 average rating, 45 reviews

Home in West Rogers Park

Mid-Century House w/Hot Tub & Parking

Hot tubBathroomQuiet

5.0 out of 5 average rating, 32 reviews

Home in Albany Park

The Jackpot | Hot Tub · Cinema · Bar · Sleeps 14

Outdoor spacesHot tubAmenities

4.88 out of 5 average rating, 94 reviews

A spacious living area features a large blue sofa adorned with a yellow accent pillow. A glass coffee table rests on a textured area rug, and a pink armchair is situated nearby. Natural light filters through large windows, highlighting the art on the wall.

Home in West Town

Hot Tub Logan Family Designer Home

Outdoor spacesBathroomParks

5.0 out of 5 average rating, 21 reviews

Home in Des Plains

Home with spa by O'Hare Airport

Hot tubOutdoor spacesAmenities

5.0 out of 5 average rating, 18 reviews

A warm living room setting showcases two comfortable armchairs and a wooden coffee table at the center. Built-in bookshelves line the walls, displaying personal items and décor. Soft lighting from a nearby lamp enhances the cozy ambiance, while large windows allow for natural light.

Home in Oak Park

Elegant 4bedroom, 5 bathroom home on a great block

Outdoor spacesFamilyIndoor spaces

Other holiday rentals with a spa

5.0 out of 5 average rating, 8 reviews

Apartment in Uptown

The Velvet Manor | Luxe 3BR • Jacuzzi • Garage

Air conditioningLocationBeach

5.0 out of 5 average rating, 55 reviews

Apartment in Ravenswood

Hygge Hideaway

Outdoor spacesHot tubLayout

4.91 out of 5 average rating, 86 reviews

An indoor swimming pool features clear blue water, with lane markings along the edges. Sunlight streams through large windows, illuminating the space. Comfortable seating is positioned nearby, accompanied by lush green plants that enhance the serene environment.

Apartment in The Loop

Metropolitan Escape (Indoor Pool • Fitness Center)

BathroomHot tubWalkability

4.67 out of 5 average rating, 54 reviews

Apartment in Wicker Park

Stylish Unit in Wicker Park| Whirlpool Tub|Balcony

Hot tubBathroomCondition

4.89 out of 5 average rating, 9 reviews

Apartment in Lake View

Spacious and Ideally located in the Lakeview area

BathroomQuietParking

4.85 out of 5 average rating, 46 reviews

Apartment in West Town

Luxury 3BD Penthouse – Private Patio+Skyline Views

Outdoor spacesBathroomKitchen

4.86 out of 5 average rating, 49 reviews

Apartment in South Side

Comfy Near Downtown Chicago

BathroomPetsWalkability