A city skyline with modern skyscrapers, a large museum, and a waterfront park.

Skokie Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

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)
"Our host Craig did a great job of being available and the home worked perfectly for our visit with grandkids"
United States
Nancy S.
The price is HK$6,132
HK$9,891 total
includes taxes & fees
3 Jul - 4 Jul
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
ENVITAE Hotel, 4BR Luxury Modern Apartments
TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is HK$1,874
HK$3,895 total
includes taxes & fees
26 Jul - 27 Jul
River North Rooftop With In and Out Parking 1
Games room

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
The price is HK$1,354
HK$5,158 total
includes taxes & fees
29 Jun - 30 Jun
4BR Retreat w/ Theater, Arcade, Gym and Firepit
TV, offices

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
The price is HK$3,592
HK$7,665 total
includes taxes & fees
26 Jul - 27 Jul
Modern West Loop Gem-City Views & Prime Location 2
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,199 reviews)
"Great location"
United States
JAVIER
The price is HK$1,193
HK$1,631 total
includes taxes & fees
1 Jul - 2 Jul
Sentral Michigan Avenue
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,239
HK$1,648 total
includes taxes & fees
30 Jun - 1 Jul
LIVN Millennium Park Downtown Chicago Studio
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is HK$3,333
HK$6,619 total
includes taxes & fees
9 Jul - 10 Jul
Premium Urban 4BR - Perfect Mix of Comfort & Location
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$1,223
HK$1,640 total
includes taxes & fees
1 Jul - 2 Jul
LIVN West Loop Chicago Classic Queen Studio
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is HK$5,191
HK$8,816 total
includes taxes & fees
29 Jul - 30 Jul
Downtown Chicago Stay with Free In & Out Parking 5
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
Beautiful Unit CHI in Prime River North - 2
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is HK$1,785
HK$2,289 total
includes taxes & fees
30 Jun - 1 Jul
Level Chicago – Old Town
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is HK$1,811
HK$3,901 total
includes taxes & fees
30 Jun - 1 Jul
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Smart TV, fireplace, offices

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.2 out of 10, Wonderful, (7 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Paper towels

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Great place! "
United States
Isabella T.
The price is HK$1,059
HK$1,980 total
includes taxes & fees
29 Jun - 30 Jun
Just remodeled apartment close to airport and mall
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is HK$2,338
HK$5,280 total
includes taxes & fees
6 Jul - 7 Jul
Vintage Urban Retreat
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (84 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is HK$910
HK$1,705 total
includes taxes & fees
5 Jul - 6 Jul
Master qtr close to nature & easy urban facilities
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is HK$2,502
HK$5,333 total
includes taxes & fees
21 Jul - 22 Jul
South Loop Rooftop With In and Out Parking 2
Terrace/patio

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (50 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is HK$953
HK$2,080 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Interior

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (101 reviews)
"Everything was good!"
United States
Brio
The price is HK$1,179
HK$2,454 total
includes taxes & fees
6 Jul - 7 Jul
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"R"
Diana 1-night trip
Posted less than an hour ago
Hyatt Regency O'Hare 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!

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Skokie is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease 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 23 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 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.