Ski-in/Ski-out holiday rentals in Chicago

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Chicago

Guests agree: These ski-in/ski-out homes are highly rated for location, cleanliness and more.

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The rooftop pool area is surrounded by lounge chairs and umbrellas, providing space for relaxation. Lush greenery is visible along the perimeter, while the cityscape and nearby buildings create a vibrant backdrop. The pool water is inviting, reflecting the clear sky above.

Apartment in Evergreen Park

Luxurious Condo at lakeshore

Our stunning condo in downtown features: 3 queen beds, 2 master bedrooms with 2 Bath Enjoy modern amenities including a fully equipped kitchen, washer & dyer + Extra Pillows & sheets offers Epic amenities - Co-Working Hubs - Pool & Sundeck with breathtaking views - Parking - Game & Billiards Room - 24/7 Fitness Center - Yoga & Meditation Lounge - Spa & Sauna - Transportation Access - Grilling Area just a 5-minute walk from the iconic Chicago Bean and with a Huge park right under the building.

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.

Condo in Burbank

Iconic Style, Charming Lake View

Enjoy breathtaking views of the lake and boats, with Gorgeous sunrises and sunsets. And Experience the ultimate in luxury and comfort in this exquisite high-rise apartment. This apartment offers the perfect blend of city life and relaxation. This spacious unit features a bedroom with a king-sized bed, a fully equipped kitchen, a large TV, and high-speed WiFi. Premium amenities include an indoor pool available all seasons, spa, hot tub, library, work area with computers, gym, and bar & Much More.

The spacious bedroom features a king bed with soft bedding, complemented by an accent chair and a lamp. Large windows offer a panoramic view of Chicago’s skyline, allowing natural light to fill the room while city details are visible outside.

Condo in Oak Lawn

Best view and luxury style, Located in Downtown

Experience the best view of your life Chicago's iconic landmarks from this high-rise apartment. Located downtown,you can see Wacker Drive, the lake, Navy Pier, the river,Trump tower from your balcony and room , The place features a spacious bedroom with a king bed , comes fully equipped with essentials, kitchen. large TV, and high WiFi. With premium amenities pool, spa, hot tub, library ,work area,computers,gym, bar. offers the perfect blend of luxury, comfort for a best city life experience

Superhost

An open-concept kitchen and living area features a modern design, highlighted by sleek cabinetry and a spacious island with seating. Natural light fills the room, accentuating the contemporary fixtures and appliances. A comfortable couch is positioned in the inviting living space, creating a perfect gathering spot.

Home in Chicago

4.87 out of 5 average rating, 45 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home with a separated basement apartment nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC.

A spacious bedroom is illuminated by natural light from large windows showcasing city skyline views. A plush bed with white bedding is complemented by decorative striped pillows. A minimalist nightstand is positioned beside the bed, and a glass door opens to a balcony.

Apartment in Cicero

Scarface Top Richest Lifestyle In Chicago

experience Luxury and Elegance City lifestyle in this Epic Tower and one of the best buildings in the center of Chi Downtown📍 Enjoy Gorgeous skyline views from two rooftop lounges Apartment Features & Amenities: 2 Master bedrooms, 3 Beds, 2 Bath & A Balcony With breathtaking views 1st room 1 King Bed 2nd room 2 Twin beds Fully furnished Fully equipped Kitchen Washer & Dryer WiFi -Parking -Game & Billiards Room -24/7 Gym -Spa & Sauna -Transportation Nearby -Grilling Area -Epic Library

A spacious living area features large windows showcasing city views. A modern sofa with accent pillows faces a flat-screen TV, while stylish teal chairs complement the minimalist design. The open layout connects to a fully equipped kitchen visible in the background.

Apartment in Near North Side

4.76 out of 5 average rating, 33 reviews

3BR Luxury Modern Apartment

This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most desirable locations. Flooded with natural sunlight the spacious living room, fully equipped kitchen and bedrooms open up to a stunning mesmerizing view. The modern apartment building offers a sun-filled outdoor pool, a fitness center and beautiful appointed outdoor courtyard. Enjoy those summer days in your luxury apartment or the amenities outside.

The exterior of a modern split-level house is presented, featuring a vibrant blue facade and large windows. A pathway leads to the entrance, surrounded by well-maintained landscaping and a manicured lawn. A driveway accommodates parked vehicles, with a garage visible on the right.

Home in Rolling Meadows

4.62 out of 5 average rating, 39 reviews

Modern townhouse in Rolling Meadows

Welcome to this Modern Casa Exelente location, Rolling Meadows on. Bring your family, guests can check in without time restrictions, ! This clean and safe space is clean and safe, …1 first floor of this house all complete and private, It has 3 bedrooms, living room, kitchen, dining room, bathroom, terrace, ! luxury kitchen! The images say more than a thousand words, ! Just 20 min to O’Hare, and 20 min Allstate Arena, and 7 min Woodfield Mall

A cozy dining area features a dark table and four chairs, situated on a patterned rug against a warm wall. A large TV is mounted nearby, with decorative shelves holding blue and green vases. The kitchen area, adjacent to this space, includes a counter with a sink.

Private room in Bolingbrook

5 out of 5 average rating, 4 reviews

A place to quietly enjoy nature

Bring the whole family to this great place with lots of room for fun. If you love nature, walking in the woods by the river this is the place to be. We are within walking distance of great restaurants movie theaters etc... Arrangements can be made with host for pick up/ drop off at the airport or anywhere else, and any other type transportation services.

Guest favourite

A light-filled living area features a cozy fireplace surrounded by a stylish brick wall. A comfortable seating arrangement includes two neutral-toned armchairs and a wooden coffee table. Large glass doors open to a private balcony, inviting natural light and offering views of exterior greenery.

Apartment in Lisle

4.8 out of 5 average rating, 5 reviews

2BR w/Balcony, Fireplace & Wi-Fi

Stylish 2BR in serene Four Lakes community. Fully furnished with all utilities, Wi-Fi, and 2 rare front-row parking spots included. Enjoy a cozy fireplace, private balcony with tree views, and peaceful resort-style amenities. Ideal for traveling pros near top hospitals. Quiet, nature-filled setting perfect for work and relaxation.

Superhost

A workspace is positioned against a wall, featuring a teal desk and a grey chair. Above, two abstract art pieces add a touch of color. To the right, a shelving unit offers organized storage, complemented by a woven basket. The space has a clean, modern aesthetic.

Private room in Albany Park

4.8 out of 5 average rating, 20 reviews

Cozy Private Basement Room | Mini Fridge | TV

This is the basement room in a duplex down first floor apartment in Albany park neighborhood of Chicago. Upstairs has shared bathroom & shower, common areas like kitchen and living room. Laundry is next to the bedroom in the basement as well. Free wifi, kitchen is full with appliances. Gas and electric included.