Ski-in/Ski-out holiday rentals in Chicago

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

Top-rated ski-in/out rentals in Chicago

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

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Superhost

Home in Chicago

4.89 out of 5 average rating, 27 reviews

Executive Contemporary Duplex

AndrielRating, 5 stars2 weeks ago

Olusesan had a clean and peaceful space. I was only a couple of miles away from the concert venue to see Beyoncé. We had our own parking space and Hyde Park was such a cute little community. We did not want to leave! Thank you so much for your hospitality. May God bless you and all of your spaces. 🙏🏽🙏🏽

Superhost

Private room in Bolingbrook

5 out of 5 average rating, 4 reviews

A place to quietly enjoy nature

AlejandraRating, 5 stars14 months ago

Very beautiful home! 🏡 It was better in person than we expected! It felt like we had our mini home in the meantime while we were in the process on getting our new home here 😊 Manasse and his wife were both loving, friendly and funny as well throughout our whole stay. Definitely recommend this spot best for your buck & so many places in the area close by and sooo much room and very cozy feels like you’re staying at a family members place ☺️

Private room in North Park

4.6 out of 5 average rating, 10 reviews

Cozy Private Basement Room | Mini Fridge | Desk

RalphRating, 5 stars7 months ago

The place is amazing like brand new home with smart TV, in unit laundry and kitchen. In terms of location, it has easy access to Kimball Brown Line Station (400m away) and CTA Bus #93 to Evanston. You can also get to Mexican, Persian, Korean, Brazilian restaurants within walking distance. Thus, I would like to stay in the same place for my visit in Chicago in 2025.

Home in Des Plaines

4.63 out of 5 average rating, 38 reviews

House 1 minute from O'hare Airport

JustinRating, 5 stars2 weeks ago

Fantastic place for a weekend with some friends. I had multiple friends staying over from out of town for a convention and this place was perfect for our needs. The host was quick to respond and the house was clean and comfortable. Great stay, would be interested again at some point

Flat 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.

Apartment 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.

Apartment 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

Flat 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

Flat in Near North Side

4.81 out of 5 average rating, 27 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.

Flat in Lisle

New place to stay

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—pool, gym, ski hill, and more. Ideal for traveling pros near top hospitals. Quiet, nature-filled setting perfect for work and relaxation.

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Popular amenities for Chicago ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

Superhost

Home in Chicago

4.89 out of 5 average rating, 27 reviews

Executive Contemporary Duplex

AndrielRating, 5 stars2 weeks ago

Olusesan had a clean and peaceful space. I was only a couple of miles away from the concert venue to see Beyoncé. We had our own parking space and Hyde Park was such a cute little community. We did not want to leave! Thank you so much for your hospitality. May God bless you and all of your spaces. 🙏🏽🙏🏽

Home in Rolling Meadows

4.57 out of 5 average rating, 28 reviews

Casa Moderna adosada, en Rolling Meadows

ChesnaRating, 5 stars1 month ago

its an amazing place and im glad i got to stay there 5s all across the board

Superhost

Private room in Bolingbrook

5 out of 5 average rating, 4 reviews

A place to quietly enjoy nature

AlejandraRating, 5 stars14 months ago

Very beautiful home! 🏡 It was better in person than we expected! It felt like we had our mini home in the meantime while we were in the process on getting our new home here 😊 Manasse and his wife were both loving, friendly and funny as well throughout our whole stay. Definitely recommend this spot best for your buck & so many places in the area close by and sooo much room and very cozy feels like you’re staying at a family members place ☺️

Home in Des Plaines

4.63 out of 5 average rating, 38 reviews

House 1 minute from O'hare Airport

JustinRating, 5 stars2 weeks ago

Fantastic place for a weekend with some friends. I had multiple friends staying over from out of town for a convention and this place was perfect for our needs. The host was quick to respond and the house was clean and comfortable. Great stay, would be interested again at some point

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Ski-in/out apartment rentals

Private room in North Park

4.6 out of 5 average rating, 10 reviews

Cozy Private Basement Room | Mini Fridge | Desk

RalphRating, 5 stars7 months ago

The place is amazing like brand new home with smart TV, in unit laundry and kitchen. In terms of location, it has easy access to Kimball Brown Line Station (400m away) and CTA Bus #93 to Evanston. You can also get to Mexican, Persian, Korean, Brazilian restaurants within walking distance. Thus, I would like to stay in the same place for my visit in Chicago in 2025.

Apartment in River North

4.33 out of 5 average rating, 9 reviews

voco: Balcony & City View

BrookeRating, 5 stars2 weeks ago

Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.

Apartment in Oak Lawn

Best view and luxury style, Located in Downtown

Apartment in Burbank

Iconic Style, Charming Lake View

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