
Apartment holiday rentals in Skokie
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Skokie
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Skokie apartment rentals
Weekly apartment rentals

Evanston 2BR 2Bth 1 Blk to Beach
Really comfortable home with thoughtful details. Easy access to many parks and restaurants, and also close to everything we needed for our family event. Sheila was very warm and helpful. There was more traffic than I expected (Evanston is hopping!), but we still always found parking within half a block. Great stay!

The Shop - Trendy Studio in the heart of Wilmette
Great location and super clean. Easy drive to Northwestern. A little nosy being in the alley, but a sound machine was provided and solved the problem. Would definitely stay again.

cozy grand studio 2nd floor/near lake/public tran.
Beautiful location and well furnished. No complaints, surrounding folks in the community are friendly. Tap into Mores Liquor very friendly staff gave me the tips and tricks in the area and what to do. Thank you Cozy Nest for hosting my wife and I! Much Appreciated!!

Clark & Balmoral - the Heart of Andersonville
At first I couldn’t believe so many 5 star reviews—and now I know why. Because you can’t give a 6. We were between business trips and have a child who lives Chicago so we thought we’d make a weekend of it rather than flying home. Lovely, homey, classy, unique, comfortable, warm and very cool all in one place. You need only to roll out of the door to find great food, great people and great fun. Thank you for opening your home to us.

New renovation|1BR|Stylish|Modern|Next to the Lake
Clean, comfortable, and beautifully appointed apt. Emily and Roya are helpful and communicative, and all the instructions and photos made things very easy. Would happily stay there again!

3 BR Evanston Apt near Chicago
We only stayed one night with our 10- and 7-year-old, but we instantly fell in love with this place. It is absolutely GORGEOUS. We brought games and art supplies for the kids, but honestly didn’t need them—the house already had everything we needed: a deck of cards, magazines, vinyls, a light-up L train tracker, and TABLE TENNIS! The thoughtful touches didn’t stop there. The host provides super clear instructions for everything—how to use the showers, where the trash goes, what to do with towels, etc.—which made this possibly the easiest stay we've ever had at an Airbnb. We just bought a house in Chicago, but we’re already looking for any excuse to come back to Evanston just so we can stay here again. Thank you so much for sharing your home with us!

Garden Unit Getaway
I stayed in Janelle’s cute basement unit for four nights when in town to visit a family member. I found the apartment to be spotlessly clean, thoughtfully appointed and had enough space to spread out a bit. The bed was comfy and there were extra towels in the bathroom, along with a nice kitchen area with many extras. There was plenty of closet space and I didn’t have trouble finding a place to plug in my mobile devices, which I often encounter with rentals. The only minus for me was the shower was a bit small, but since it was so clean and had decent water pressure, I really can’t complain. :) The apartment is in a nice, family neighborhood which seemed safe and quiet. The availability of on-street parking varied based on the time of day, but I was always able to find something within a block or two. Janelle was very responsive and communication was great. I hope to stay here again next time I am in town. Thanks, Janelle!

South Evanston Apartment - Two Bur Oaks
Guys this is one of the best apartment to stay. Very Very clean. Peaceful and quite neighborhood. Plenty of parking space, don't worry about parking. I stayed here for a week with my wife and daughter. Felt like my home. Steve & Jolie: You guys have a great apartment. Felt safe. Thanks!
Private apartment rentals

Bright Colorful Boho-Chic Studio in Lincoln Square
It was wonderful staying at Laura's place. In the heart of the city, private and peaceful place, great for my family of 3.

Stunning Retro Apartment in Andersonville
This place absolutely perfect! We were back and forth from Navy Pier for a tournament. The apartment was the perfect escape from the noise. We would definitely stay here again if we come back to the city. I can’t recommend this apartment enough. The price, for Chicago, is totally worth it!! Host is very quick to respond. The distance from the Pier to the apartment is an easy, short drive.

Full Apartment green oasis in law suite
Had a lovely stay with Lola! She was very kind and responsive :) the property was beautiful and very well kept! Definitely felt like a home away from home! Will 100% stay agin if in the area!

1 Bedroom Apartment/free parking
Comfortable apartment close to many restaurants and cafes. We had a wedding to attend to and The Grove was only 1.5 miles away. The apartment was clean and the neighbors are quiet. Uber and Lyft didn’t have a hard time finding the place and was quick. Shower has great water pressure and we didn’t have to wait long for it to get hot.

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
5 star for sure! This place is a hidden gem, its so clean and has so many little extras to make you feel at home. I found seasoning to cook with,.coffee, tea, cream and sugar..and even a couple of pods for laundry. All of that plus an easy check-in, great parking space in the back (which you will need since street parking can be dicey) and the friendly neighbors made my stay wonderful. I stayed 7 nights and it is quiet at night so I felt very safe and got a good nights rest each night. I will definitely book again!!!

Vibrant & Chic Apt On Quiet St in Andersonville
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.

Modern Lakefront Retreat with Breathtaking Views!
Great 1st floor town home on the boarder between Rogers Park and Evanston, right on the waters of Lake Michigan. Lots of sunlight (and able to watch the sunrise over Lake Michigan in the morning) and a couple of parks next door. The bathrooms (especially the showers) were great--full size, nice water pressure. I was able to work remotely while I was there without any issues. As others have noted, parking is on the street; but if you're proactive or book with Spot Hero or similar, it's very manageable. I really enjoyed my stay!

Montrose Gardens
This was a very cute one bedroom apartment. It was perfect for my husband, myself and my daughter. Extremely clean. So sweet they left treats and snacks! Host was very nice and accommodating. Would definitely stay again!
Apartment rentals with a hot tub

The Areal Oasis
What a spectacular stay! We thoroughly enjoyed our time at Stephanie's "Areal Oasis". Apartment was spotless, well decorated, very well furnished, and the view is spectacular. Stephanie was an excellent communicator and always very responsive. We thoroughly recommend staying here and hope to return.

Spacious Beautiful Condo
We came for our daughter’s graduation and stayed a few extra days to tour the city. This place was perfectly located for both occasions. It was much more spacious than we expected, and everything was very clean. We especially appreciated the fresh towels and beddings. Our only wish is that the beds were a bit larger, especially the double bed, which would be more comfortable for a couple if it were at least a queen size. That said, the beds were very comfortable. Overall, we had a wonderful stay - definitely one of our best Airbnb experiences!

Skyline Oasis: City & Lake Views
Perfect weeklong stay in Chicago! The apartment is well equipped and makes you feel right at home. The building is connected via sky bridge to Jewel making it easy to grab groceries. The location cannot be beat - easy access to West Loop, Wicker Park, River North. The hosts were fantastic and flexible with our check in times. Looking forward to coming back!

Rooftop HotTub As Seen On "Married At First Sight"
I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop
We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.

Large Studio Apartment with no cleaning fee
David and his co-host were excellent. Our family enjoyed our stay. We used to live in the Bronzeville area and love the new additions to the neighborhood. Everything met or exceeded our expectations.

Lincoln Park Haven: Balcony, Walk to Whole Foods
Loved our stay at The Foundry! The unit was beautiful and comfortable and the views were incredible. We had everything we needed and communication from Cloud9 was clear. There are great places nearby to walk for coffee and food — including an amazing Whole Foods.

Sentral 1 Bedroom Apt in South Loop Chicago
Sentral worked great for us going to a graduation for a long weekend. Unit is exactly as described, modern, and clean. Kitchen utensils are reasonable while shelves and refrig are empty save for some coffee so if going to cook/eat be sure to bring everything such as butter, spices, etc. - a Trader Joes is 3 blocks away. Price is not cheap but is very convenient and easy so on balance okay for us. Front desk is very helpful and cheerful.
Quick stats about flat rentals in Skokie
Total rentals
30 properties
Nightly prices starting at
₹3,471 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- South Side Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Chicago Holiday rentals
- Rentals with a patio Skokie
- Rentals with a fireplace Skokie
- Pet-friendly rentals Skokie
- House rentals Skokie
- Family-friendly rentals Skokie
- Rentals with a washing machine and dryer Skokie
- Rentals with outdoor seating Skokie
- Fitness-friendly rentals Skokie
- Flat rentals Cook County
- Flat rentals Illinois
- Flat rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- Washington Park Zoo
- The 606
- The Beverly Country Club
- Racine North Beach