Skokie Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Skokie holiday rentals

Smart TV, fireplace, books, video library

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is HK$2,623
HK$5,470 total
includes taxes & fees
20 May - 21 May
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Iron/ironing board, travel cot, WiFi, bed sheets

Chic Skokie Retreat - 1BR Unit in Skokie

Chic Skokie Retreat - 1BR Unit in Skokie
Skokie
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,589
HK$2,644 total
includes taxes & fees
14 Jun - 15 Jun
Chic Skokie Retreat - 1BR Unit in Skokie
TV, offices

Spacious 2BR Close to it All - Chic Apt in Skokie

Spacious 2BR Close to it All - Chic Apt in Skokie
West Dempster
9.0 out of 10, Wonderful, (2 reviews)
"Excellent communication with the host. Easy and secure access to the unit. Well furnished and perfect for my trip. So clean! "
United States
Jean W.
The price is HK$986
HK$2,039 total
includes taxes & fees
20 May - 21 May
Spacious 2BR Close to it All - Chic Apt in Skokie
Dining

1-Bedroom Pad | Cozy + All-Set

1-Bedroom Pad | Cozy + All-Set
West Dempster
8.0 out of 10, Very good, (2 reviews)
"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$869
HK$1,751 total
includes taxes & fees
26 May - 27 May
1-Bedroom Pad | Cozy + All-Set
Fridge, microwave, oven, stovetop

Skokie 1BR Stay Near Parks, Dining & Transit

Skokie 1BR Stay Near Parks, Dining & Transit
Skokie
The price is HK$673
HK$1,504 total
includes taxes & fees
19 May - 20 May
Skokie 1BR Stay Near Parks, Dining & Transit
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,159 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is HK$1,191
HK$1,628 total
includes taxes & fees
26 May - 27 May
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (754 reviews)
"Great location"
United States
Alex
Kasa Magnificent Mile Chicago
Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (477 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is HK$1,427
HK$1,868 total
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town
Exterior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is HK$1,135
HK$3,488 total
includes taxes & fees
27 May - 28 May
Modern 3BR Apartment Near North Ave Shops
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is HK$4,299
HK$8,513 total
includes taxes & fees
3 Jun - 4 Jun
Modern West Loop Gem-City Views & Prime Location 5
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"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$1,159
HK$2,059 total
includes taxes & fees
26 May - 27 May
Chic Studio in the Heart of the Gold Coast
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,268
HK$3,720 total
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is HK$1,034
HK$3,286 total
includes taxes & fees
19 May - 20 May
River North Rooftop With In and Out Parking 6
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is HK$1,214
HK$2,250 total
includes taxes & fees
20 May - 21 May
West Loop Living – Bright 1BR
Interior

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,386
HK$1,840 total
includes taxes & fees
20 May - 21 May
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"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$1,621
HK$2,823 total
includes taxes & fees
21 May - 22 May
Sunlit 1BR Apartment | Warm & Welcoming Space
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
Kasa River North Chicago
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is HK$1,699
HK$2,265 total
includes taxes & fees
20 May - 21 May
LIVN West Loop Chicago 2 BR City View
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$2,075
HK$4,658 total
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$1,041
HK$2,038 total
includes taxes & fees
19 May - 20 May
1BR Modern Luxe Apt with In-Unit Laundry
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

8/10 Good
"Clean great staff. Good location . Would recommend"
Michael 3-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago

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
  • Use the map to find apartments and other holiday homes in the Skokie neighbourhood you prefer
  • 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 North Shore Center for the Performing Arts, 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Skokie is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Skokie?

Expedia has 25 holiday rentals for your stay in Skokie.

What can I see and do in Skokie?

Schaefer's Wines and Liquors and Adagio Teas are a couple of the family-friendly sights, whereas cultural attractions include Skokie Theatre. While in the area, you can also visit popular places such as Wrigley Field and Navy Pier.

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.