Skokie Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Skokie

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (592)
"We stayed stayed at the Sentral for a business/family trip. This hotel is beautiful and accommodating. Sandra at the front desk was the sweetest and made check in a breeze, even allowing us to check in early. The room was clean, however there was a burn mark on the kitchen floor and it appeared as it was not vacuumed. Otherwise the room was wonderful, we would definitely stay here again! "
The price is AU$238
includes taxes & fees
15 Dec - 16 Dec
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is AU$101
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AU$218
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (332)
"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is AU$397
includes taxes & fees
24 Nov - 25 Nov
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is AU$208
includes taxes & fees
17 Dec - 18 Dec
Found Chicago powered by Sonder
Sonder The Burnham Apartments
3.5 star property
8.8 out of 10, Excellent, (114)
"Very convenient location, the apartment was impeccable "
The price is AU$226
includes taxes & fees
16 Dec - 17 Dec
Sonder The Burnham Apartments
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is AU$224
includes taxes & fees
11 Dec - 12 Dec
Sonder Jewelers Row
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is AU$145
includes taxes & fees
8 Dec - 9 Dec
Kasa River North Chicago
Sonder The Plymouth
3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is AU$226
includes taxes & fees
19 Dec - 20 Dec
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.6 out of 10, Exceptional, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,
Sonder The Opal
3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is AU$243
includes taxes & fees
18 Dec - 19 Dec
Sonder The Opal
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (212)
"A big, beautiful, immaculate, wonderfully furnished space 51 floors above the city. Everything in the owner's description is true. Watching the sun rise over the lake from that height was a treat. Also being able to walk to restaurants, Navy Pier, river tours, great blues clubs, plus hop the subway just a few doors away. The door staff was very helpful in stashing our luggage on both sides of our stay (be sure to "show them some kindness" for that service). "
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Experience Chicago living near United Center
9.4 out of 10, Exceptional, (12)
"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "
Experience Chicago living near United Center
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (66)
"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."
Wrigley/Southport Corridor Garden Oasis +parking!
Sonder Greektown
3.5 star property
9.0 out of 10, Wonderful, (33)
"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...
The price is AU$258
includes taxes & fees
12 Dec - 13 Dec
Sonder Greektown
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (81)
"Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Skokie
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Skokie you may be interested in

Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (8135)
"It is an old building so We were very pleased with how clean the rooms were. Tub drained slowly but did not affect our shower schedules. Radiator was a little confusing but it didn’t bother is because the weather was beautiful. Will stay again"
The price is AU$154
includes taxes & fees
27 Nov - 28 Nov
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (3549)
"Booked: two bedroom suite Condition: bed was very comfy and linens felt lovely. Bathroom was well appointed. Spotlessly clean. Rooms could use a remodel and a spruce up, BUT it was not offensively outdated and I have NO complaints on the quality of the space. Microwave also functions as a convection oven. Plates, cups, utensils, cooktop, pots and pans included. Refrigerator is fairly generously sized. Love the water bottle filler across from the elevator. Staff were fantastic, helpful and fun!...
The price is AU$189
includes taxes & fees
22 Dec - 23 Dec
River Hotel
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3263)
"This was my Bestfriend and I first time in Chicago. This property is close to a lot of shopping and some main attractions either by foot or a short car ride. I loved how the hotel has a fillable water station. I feel that was the highlight of the hotel. The rooms were a bit small but that was okay. The staff was very welcoming and attentive. Thank you again. "
The price is AU$172
includes taxes & fees
22 Dec - 23 Dec
Club Quarters Hotel, Central Loop, Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Skokie?

Yes, there are holiday rentals in Skokie close to Adagio Teas, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Skokie. Make sure you allow time to enjoy the gardens during your holiday.

What are some of the best holiday rentals that Skokie has to offer?

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!: This holiday home rental outside of Skokie is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Skokie?

Expedia has 12 holiday rentals for your stay in Skokie.

What can I see and do in Skokie?

Adagio Teas and Schaefer's Wines and Liquors are a couple of the family-friendly sights, whereas cultural attractions include North Shore Center for the Performing Arts and Skokie Theatre. While in the area, you can also visit popular places such as Wrigley Field and Michigan Avenue.

What are holiday rentals like in Skokie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Skokie. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for small groups.