Apartment holiday rentals in Skokie

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Popular amenities for Skokie apartment rentals

Weekly apartment rentals

Top guest favourite
Flat in Evanston
4.99 out of 5 average rating, 78 reviews

Evanston 2BR 2Bth 1 Blk to Beach

AnnaRating, 5 stars2 weeks ago
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!
Guest favourite
Flat in Wilmette
4.89 out of 5 average rating, 37 reviews

The Shop - Trendy Studio in the heart of Wilmette

BrookeRating, 5 stars5 days ago
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.
Guest favourite
Flat in East Rogers Park
4.92 out of 5 average rating, 36 reviews

cozy grand studio 2nd floor/near lake/public tran.

JeronRating, 5 stars1 week ago
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!!
Top guest favourite
Flat in Andersonville
5 out of 5 average rating, 77 reviews

Clark & Balmoral - the Heart of Andersonville

BethRating, 5 stars1 week ago
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.
Guest favourite
Flat in Evanston
4.9 out of 5 average rating, 91 reviews

New renovation|1BR|Stylish|Modern|Next to the Lake

AmyRating, 5 stars4 weeks ago
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!
Top guest favourite
Flat in Evanston
4.98 out of 5 average rating, 94 reviews

3 BR Evanston Apt near Chicago

Sarah KathleenRating, 5 stars3 weeks ago
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!
Superhost
Flat in West Rogers Park
4.93 out of 5 average rating, 44 reviews

Garden Unit Getaway

DawnRating, 5 stars1 week ago
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!
Top guest favourite
Flat in Evanston
4.98 out of 5 average rating, 60 reviews

South Evanston Apartment - Two Bur Oaks

KarthikRating, 5 stars2 weeks ago
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

Guest favourite
Flat in Lincoln Square
4.97 out of 5 average rating, 96 reviews

Bright Colorful Boho-Chic Studio in Lincoln Square

ShreyasRating, 5 stars1 week ago
It was wonderful staying at Laura's place. In the heart of the city, private and peaceful place, great for my family of 3.
Top guest favourite
Flat in Andersonville
4.95 out of 5 average rating, 557 reviews

Stunning Retro Apartment in Andersonville

MelissaRating, 5 stars1 week ago
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.
Top guest favourite
Flat in Highland Park
5 out of 5 average rating, 40 reviews

Full Apartment green oasis in law suite

BrookeRating, 5 stars2 weeks ago
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!
Superhost
Flat in Glenview
4.88 out of 5 average rating, 32 reviews

1 Bedroom Apartment/free parking

Ra2Rating, 5 stars4 days ago
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.
Guest favourite
Flat in Cicero
4.97 out of 5 average rating, 311 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

PatriciaRating, 5 stars6 days ago
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!!!
Top guest favourite
Flat in Andersonville
4.99 out of 5 average rating, 155 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

DianeRating, 5 stars2 weeks ago
Staying with Johana was a pleasure. The location was perfect, the house was cozy and clean. Highly recommend.
Superhost
Flat in East Rogers Park
4.74 out of 5 average rating, 117 reviews

Modern Lakefront Retreat with Breathtaking Views!

MatthewRating, 5 stars2 weeks ago
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!
Guest favourite
Flat in Irving Park
4.91 out of 5 average rating, 53 reviews

Montrose Gardens

JoyceRating, 5 stars5 days ago
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

Superhost
Flat in The Loop
4.92 out of 5 average rating, 48 reviews

The Areal Oasis

JenniferRating, 5 stars3 weeks ago
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.
Superhost
Flat in West Rogers Park
4.85 out of 5 average rating, 78 reviews

Spacious Beautiful Condo

SophiaRating, 5 stars2 days ago
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!
Guest favourite
Flat in West Loop
4.96 out of 5 average rating, 27 reviews

Skyline Oasis: City & Lake Views

NatalieRating, 5 stars2 weeks ago
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!
Superhost
Flat in Chicago
4.83 out of 5 average rating, 54 reviews

Rooftop HotTub As Seen On "Married At First Sight"

KimikoRating, 5 stars8 months ago
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!!
Top guest favourite
Flat in West Town
5 out of 5 average rating, 7 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

RimpiRating, 5 stars4 weeks ago
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.
Superhost
Flat in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars6 days ago
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.
Guest favourite
Flat in Near North Side
4.92 out of 5 average rating, 38 reviews

Lincoln Park Haven: Balcony, Walk to Whole Foods

KristenRating, 5 stars3 days ago
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.
Superhost
Flat in The Loop
4.69 out of 5 average rating, 49 reviews

Sentral 1 Bedroom Apt in South Loop Chicago

RichardRating, 5 stars1 week ago
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

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  5. Skokie
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