Skokie Holiday Rentals

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Skokie holiday rentals

Fridge, microwave, oven, stovetop
1-Bedroom Pad | Cozy + All-Set

Apartment in West Dempster

1-Bedroom Pad | Cozy + All-Set
8.0 out of 10, Very good, (2)
"This was a great space. The location was perfect and we had everthing we needed. We would definitely stay here again. "
United States
Amanda M.
The price is HK$490
HK$1,285 total
includes taxes & fees
5 Jan - 6 Jan 2026
1-Bedroom Pad | Cozy + All-Set
Fridge, microwave, oven, stovetop
Spacious 2BR Close to it All - Chic Apt in Skokie

Apartment in West Dempster

Spacious 2BR Close to it All - Chic Apt in Skokie
The price is HK$467
HK$1,374 total
includes taxes & fees
28 Dec - 29 Dec
Spacious 2BR Close to it All - Chic Apt in Skokie
Fridge, oven, stovetop, coffee/tea maker
Chic Skokie Retreat - 1BR Unit in Skokie

Apartment in Skokie

Chic Skokie Retreat - 1BR Unit in Skokie
2.0 star property
The price is HK$490
HK$1,285 total
includes taxes & fees
6 Jan - 7 Jan 2026
Chic Skokie Retreat - 1BR Unit in Skokie
Fridge, microwave, oven, stovetop
Skokie Gem - 1BR on Davis St!

Apartment in Skokie

Skokie Gem - 1BR on Davis St!
The price is HK$490
HK$1,285 total
includes taxes & fees
4 Jan - 5 Jan 2026
Skokie Gem - 1BR on Davis St!
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Holiday Home in Skokie

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is HK$2,324
HK$5,149 total
includes taxes & fees
5 Jan - 6 Jan 2026
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1020)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is HK$919
HK$1,307 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
8.4 out of 10, Very good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is HK$1,023
HK$1,201 total
includes taxes & fees
4 Jan - 5 Jan 2026
Chicago luxury home suites
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$537
HK$1,287 total
includes taxes & fees
4 Jan - 5 Jan 2026
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek 1BR Apt w/ Laundry
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$490
HK$1,310 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,310 total
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (405)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
TV, offices
South Loop Rooftop With In & Out Parking 1

Apartment in Downtown Chicago

South Loop Rooftop With In & Out Parking 1
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is HK$801
HK$2,472 total
includes taxes & fees
8 Jan - 9 Jan 2026
South Loop Rooftop With In & Out Parking 1
4 bedrooms, iron/ironing board, travel cot, WiFi
Modern West Loop Gem-City Views & Prime Location 5

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 5
2.0 star property
8.0 out of 10, Very good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
Modern West Loop Gem-City Views & Prime Location 5
Terrace/patio
River North Private Balcony With In and Out Parking

Apartment in Downtown Chicago

River North Private Balcony With In and Out Parking
10.0 out of 10, Exceptional, (3)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is HK$778
HK$2,395 total
includes taxes & fees
21 Jan - 22 Jan 2026
River North Private Balcony With In and Out Parking
Interior
Downtown Chicago Stay with Free In & Out Parking 4

Apartment in Downtown Chicago

Downtown Chicago Stay with Free In & Out Parking 4
2.0 star property
The price is HK$957
HK$2,654 total
includes taxes & fees
5 Jan - 6 Jan 2026
Downtown Chicago Stay with Free In & Out Parking 4
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.
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Top Skokie Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"The lady who checked us in (the countess) was very friendly and welcoming. Even though she was the only person working the front desk, she did not get frazzled or curt. She was great! Room was beautiful and had an amazing view!"
Elise 2-night trip
Posted 3 days ago
The Royal Sonesta Chicago Downtown

Find out more about Skokie

Search for holiday rentals in Skokie on Expedia! You can easily find your home rentals, villas, holiday apartments in Skokie using one of the methods below:

  • View our selection of featured holiday rentals in Skokie
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  • Enter your travel dates to view the best deals on holiday rentals in Skokie while they last

Look no further and take a look at our great range of rental properties in Skokie!

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Frequently asked questions

Are there holiday rentals in Skokie?

Yes, there are holiday rentals in Skokie close to Emily Oaks Nature Center, 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Skokie offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Skokie?

Expedia has 22 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 Skokie Theatre and North Shore Center for the Performing Arts. 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.