Skokie Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Dec 3 - Dec 4
Tomorrow
Dec 4 - Dec 5
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Skokie

Fridge, microwave, oven, stovetop
Spacious 2BR Close to it All - Chic Apt in Skokie

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

Skokie
$165 nightly
The price is $177
Dec 8 - Dec 9
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
Fridge, microwave, oven, stovetop
1-Bedroom Pad | Cozy + All-Set

1-Bedroom Pad | Cozy + All-Set

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.
$153 nightly
The price is $165
Jan 1 - Jan 2, 2026
Total with taxes and fees
1-Bedroom Pad | Cozy + All-Set
Fridge, microwave, oven, stovetop
Skokie Gem - 1BR on Davis St!

Skokie Gem - 1BR on Davis St!

Skokie
$145 nightly
The price is $156
Dec 7 - Dec 8
Total with taxes and fees
Skokie Gem - 1BR on Davis St!
Fridge, microwave, oven, stovetop
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, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
$644 nightly
The price is $689
Dec 4 - Dec 5
Total with taxes and fees
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Interior
Luxury Home - Pool Table/Bar/Patio

Luxury Home - Pool Table/Bar/Patio

Skokie
10.0 out of 10, Exceptional, (4)
"Perfect for what we needed!"
United States
William H.
$816 nightly
The price is $873
Dec 4 - Dec 5
Total with taxes and fees
Luxury Home - Pool Table/Bar/Patio
Outdoor dining
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

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.
$787 nightly
The price is $842
Dec 4 - Dec 5
Total with taxes and fees
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
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
$126 nightly
The price is $148
Dec 7 - Dec 8
Total with taxes and fees
Sentral Michigan Avenue
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
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
$176 nightly
The price is $207
Dec 4 - Dec 5
Total with taxes and fees
Chicago luxury home suites
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

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.
$167 nightly
The price is $182
Dec 7 - Dec 8
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"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.
$145 nightly
The price is $159
Dec 7 - Dec 8
Total with taxes and fees
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Downtown Chicago
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.
$145 nightly
The price is $159
Dec 4 - Dec 5
Total with taxes and fees
Sun-Drenched 1BR Apartment
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

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
$149 nightly
The price is $166
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

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.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
$153 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
4 bedrooms, iron/ironing board, travel crib, WiFi
Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5

2.0 star property
Downtown Chicago
$114 nightly
The price is $134
Dec 17 - Dec 18
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
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
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (392)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$215 nightly
The price is $252
Dec 14 - Dec 15
Total with taxes and fees
Level Chicago – Old Town
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 5 - Dec 6
Total with taxes and fees
Kasa River North Chicago
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$324 nightly
The price is $355
Dec 14 - Dec 15
Total with taxes and fees
River North Rooftop With In and Out Parking 1
Interior
Your Chicago get Away

Your Chicago get Away

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.
$392 nightly
The price is $430
Dec 11 - Dec 12
Total with taxes and fees
Your Chicago get Away
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Skokie Hotel Reviews

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Service was excellent!"
Dany Hernandez 4-night trip
Posted 15 hours ago
LondonHouse Chicago, Curio Collection by Hilton

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 $110 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?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This vacation home rental near Skokie offers a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Skokie?

Expedia has 21 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.