Apartment holiday rentals in Skokie

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Popular amenities for Skokie apartment rentals

Weekly apartment rentals

Top Guest favourite
Apartment 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
Apartment 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.
Top Guest favourite
Apartment 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
Apartment 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!
Guest favourite
Apartment in East Rogers Park
4.88 out of 5 average rating, 8 reviews

COZY unit near Michigan Lake 2nd floor/no elevator

AliyahRating, 5 stars1 month ago
Loved my stay! There was a little bit of confusion when it came to checking in and they responded to me almost immediately—which I was so grateful for after a long day of traveling. The amenities were great (me and that Keurig got along like a house on fire) and the apartment was, as described, cozy. It was perfect for me as someone who was traveling solo. After I checked out, they saw that I’d accidentally left my glasses behind and reached out to me to make sure I could grab them. Just a stellar experience from start to finish. Will definitely try to stay here again if the opportunity arises!
Guest favourite
Apartment in Norwood Park
5 out of 5 average rating, 40 reviews

The Norwood Nook –Walkable , Near O’Hare & Metra!

ShreemRating, 5 stars1 week ago
Peaceful place feels like home, cozy and nice, winters would be more fun, than time I visited, and super comfy. Tara is a great host and you can always reach out to her! The neighborhood is so nice, saw dogs on porches and people around.
Superhost
Apartment in Evanston
4.9 out of 5 average rating, 83 reviews

Special Skokie Space 2mi to NW & downtown Evanston

MaxRating, 5 stars1 month ago
This was a very cozy place to stay with a couple of friends, while spending the weekend at concerts and exploring the city!
Superhost
Apartment 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!

Private apartment rentals

Guest favourite
Apartment in Forest Park
4.87 out of 5 average rating, 119 reviews

City-Accessible Basement Retreat

AmyRating, 5 stars2 weeks ago
Christopher’s place was perfect for our needs! The place was very roomy, the kitchen and bathroom was spotless and spacious, and the bed was comfortable. The neighborhood was quiet and calm with more than enough easy and free parking. The metro was less than a 10 minute walk which was perfect for us getting in and out of the city easily. They also allowed us to drop off our luggage before check in hours which we greatly appreciated. Needless to say, we enjoyed our stay and would strongly recommend staying here.
Guest favourite
Apartment 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
Apartment 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.
Guest favourite
Apartment in Maywood
4.92 out of 5 average rating, 101 reviews

Cozy guest studio, great for couples!

BrittanyRating, 5 stars1 week ago
Lovely basement studio in very nice neighborhood. Easy drive to nearby neighborhoods or downtown area. Highly recommend if you’re looking for a comfortable stay!
Top Guest favourite
Apartment 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.
Guest favourite
Apartment in Oak Park
4.86 out of 5 average rating, 292 reviews

Cozy and Character-Rich Chicago Style, Tv NFL PASS

LoganRating, 5 stars1 week ago
Fantastic place! Very safe! Really enjoyed how close it was to the city without actually being in the city!
Guest favourite
Apartment in Irving Park
4.91 out of 5 average rating, 53 reviews

Montrose Gardens

JoyceRating, 5 stars6 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!
Superhost
Apartment in West Rogers Park
4.84 out of 5 average rating, 112 reviews

Personal Parking, In-Unit Laundry & King Bed

KelseeRating, 5 stars3 weeks ago
It was a wonderful stay! The place looked exactly like the photos and had everything one could need for a stay. Sharon recommended local restaurants and events that were around as we traveled over a holiday weekend. She was very responsive and helpful. The space is in the basement of her home and she was very respectful with not being super loud or walking hard. A wonderful stay for a wonderful price.

Apartment rentals with a hot tub

Superhost
Apartment 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
Apartment 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
Apartment 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
Apartment 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!!
Superhost
Apartment in Chicago
4.88 out of 5 average rating, 16 reviews

Large Studio Apartment with no cleaning fee

Latrice Rating, 5 stars1 week 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.
Top Guest favourite
Apartment 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.
Guest favourite
Apartment 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.
Top Guest favourite
Apartment in Belmont Cragin
4.98 out of 5 average rating, 118 reviews

Belmont Pleasures - hot tub / arcade gaming room

AustinRating, 5 stars5 days ago
Stay was great and Mariam was a super host. The space was exactly as pictured and all the games were a blast. Miriam even checked in a couple times to make sure we had everything we need and that we were having a good time. For sure would stay here again.

Quick stats about apartment rentals in Skokie

  • Total rentals

    30 properties

  • Nightly prices starting at

    $67 NZD 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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