Skokie Holiday Rentals

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Holiday Rentals in Skokie

Apartment in Skokie

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 AU$241
includes taxes & fees
3 Dec - 4 Dec
1-Bedroom Pad | Cozy + All-Set

Apartment in Skokie

The price is AU$294
includes taxes & fees
8 Dec - 9 Dec
Spacious 2BR Close to it All - Chic Apt in Skokie

Apartment in Skokie

The price is AU$241
includes taxes & fees
7 Dec - 8 Dec
Skokie Gem - 1BR on Davis St!

Holiday Home in Skokie

10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
The price is AU$1,017
includes taxes & fees
3 Dec - 4 Dec
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Holiday Home in Skokie

10.0 out of 10, Exceptional, (4)
"Perfect for what we needed!"
United States
William H.
The price is AU$1,347
includes taxes & fees
3 Dec - 4 Dec
Luxury Home - Pool Table/Bar/Patio

Holiday Home in Skokie

9.4 out of 10, Exceptional, (6)
"Super clean and great neighborhood still close to downtown. A fun 20 min uber drive away! "
United States
Kurt P.
The price is AU$1,299
includes taxes & fees
3 Dec - 4 Dec
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

4BR Corporate Suite Central and Modern

2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
4BR Corporate Suite Central and Modern

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is AU$225
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is AU$456
includes taxes & fees
3 Dec - 4 Dec
Chicago luxury home suites

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is AU$261
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is AU$246
includes taxes & fees
7 Dec - 8 Dec
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is AU$282
includes taxes & fees
7 Dec - 8 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"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 AU$256
includes taxes & fees
1 Jan - 2 Jan 2026
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
The price is AU$246
includes taxes & fees
3 Dec - 4 Dec
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

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 AU$260
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (391)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town

Apartment in Downtown Chicago

2.0 star property
The price is AU$244
includes taxes & fees
17 Dec - 18 Dec
Modern West Loop Gem-City Views & Prime Location 5

Apartment in Downtown Chicago

9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is AU$479
includes taxes & fees
7 Dec - 8 Dec
River North Rooftop With In and Out Parking 1

Apartment in Downtown Chicago

8.4 out of 10, Very good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is AU$604
includes taxes & fees
10 Dec - 11 Dec
Your Chicago get Away

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North 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.

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Top Skokie Hotel Reviews

Find out more about Skokie

Everything you need to know about Skokie holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Skokie holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Skokie holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Skokie holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Skokie. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Skokie holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Skokie holiday rentals we have selected for you start as low as AU$174 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Skokie rentals

At Expedia, we put the best Skokie holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Skokie rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Skokie holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Skokie. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This holiday home rental outside of Skokie offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Skokie?

Expedia has 21 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.