Skokie Vacation Rentals

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Check prices for these dates

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Skokie vacation 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.
$153 nightly
The price is $165
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
$165 nightly
The price is $177
Dec 30 - Dec 31
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
Fridge, microwave, oven, stovetop
Skokie Gem - 1BR on Davis St!

Apartment in Skokie

Skokie Gem - 1BR on Davis St!
$153 nightly
The price is $165
Jan 4 - Jan 5, 2026
Total with taxes and fees
Skokie Gem - 1BR on Davis St!
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
$153 nightly
The price is $165
Jan 4 - Jan 5, 2026
Total with taxes and fees
Chic Skokie Retreat - 1BR Unit in Skokie
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Vacation 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.
$619 nightly
The price is $662
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Outdoor dining
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

Vacation Home in Skokie

Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker
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.
$787 nightly
The price is $842
Jan 4 - Jan 5, 2026
Total with taxes and fees
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
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
$550 nightly
The price is $646
Dec 30 - Dec 31
Total with taxes and fees
ENVITAE Hotel 4 Bedroom Luxury Apartments
Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
$143 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"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
$132 nightly
The price is $156
Dec 30 - Dec 31
Total with taxes and fees
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
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
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
$149 nightly
The price is $166
Jan 4 - Jan 5, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (5)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
West Loop Living – Bright 1BR
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.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish 1BR in West Loop
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$174 nightly
The price is $191
Jan 1 - Jan 2, 2026
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
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.
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sun-Drenched 1BR Apartment
Business center
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
$218 nightly
The price is $256
Jan 5 - Jan 6, 2026
Total with taxes and fees
Kasa River North Chicago
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
$153 nightly
The price is $168
Jan 7 - Jan 8, 2026
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
Interior
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 out of 10, Exceptional, (4)
"Great stay. I'm from the area but had friends visiting from out of town. This was a great location only a quick walk to Michigan Avenue and 15 minutes from the loop. The apartment was spacious, and I appreciated having disney plus/netflix signed into the TV. The check-in and check-out was really easy with an accompanying video and easy lockbox location. Host/company was also very communicative, and let me grab something I forgot in my rental after checking out!Parking space was also clutch, just...
United States
Amarah K.
$283 nightly
The price is $314
Jan 5 - Jan 6, 2026
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Apartment in Hyde Park

Modern Studio Near UChicago
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
$137 nightly
The price is $151
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern Studio Near UChicago
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 traveler
$153 nightly
The price is $168
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sleek 1BR Apt w/ 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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Easy check in and check out, staff were very friendly, room was great, bed was very comfortable. The hotel was also very clean. We loved the location. It was so close to Michigan Avenue, but it was quiet. "
Cindy 1-night trip
Posted 23 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Skokie

Everything you need to know about Skokie vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Skokie vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Skokie vacation 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 low season months. For more hustle and bustle, you may prefer to visit Skokie in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Skokie rentals

At Expedia, we put the best Skokie vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Skokie?

Yes, we offer vacation rentals in Skokie close to Emily Oaks Nature Center, or you can select a secluded option if you're looking for extra privacy while you relax. Tourists like the array of shops and top-notch restaurants in Skokie. Make sure you allow time to enjoy the gardens during your vacation.

What are some of the best vacation home rentals in Skokie?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This vacation home rental near Skokie offers a patio, a barbecue grill, 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 vacation rentals are there in Skokie?

Expedia has 22 vacation 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 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 like Wrigley Field and Michigan Avenue.

What are vacation rentals like in Skokie?

Vacation rentals are private properties you can stay in for a couple days or more in Skokie. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.