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

Skokie Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Skokie vacation rentals

A dining area with a round table, four chairs, a chandelier, and a kitchen with white cabinets and a countertop.

1. 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.
$188 nightly
The price is $206
Nov 1 - Nov 2
Total with taxes and fees
1-Bedroom Pad | Cozy + All-Set
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

2. 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.
$238 nightly
The price is $261
Oct 5 - Oct 6
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
A modern kitchen with dark cabinets, stainless steel appliances, a black faucet, and a clock on the wall.

3. Skokie 1BR Stay Near Parks, Dining & Transit

Skokie 1BR Stay Near Parks, Dining & Transit
Skokie
$249 nightly
The price is $268
Oct 5 - Oct 6
Total with taxes and fees
Skokie 1BR Stay Near Parks, Dining & Transit
A neatly made bed with a white comforter and two pillows, flanked by two bedside tables with lamps and clocks.

4. Chic Skokie Retreat - 1BR Unit in Skokie

Chic Skokie Retreat - 1BR Unit in Skokie
Skokie
6.0 out of 10, (2 reviews)
$237 nightly
The price is $254
Oct 15 - Oct 16
Total with taxes and fees
Chic Skokie Retreat - 1BR Unit in Skokie
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

5. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (274 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
$218 nightly
The price is $250
Oct 29 - Oct 30
Total with taxes and fees
The Gem Museum Suites
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (57 reviews)
"Great apt, excellent host"
United States
Colleen B.
$245 nightly
The price is $278
Oct 6 - Oct 7
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A modern bedroom with a bed, a sofa, and a hanging plant.

7. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (99 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
$118 nightly
The price is $145
Oct 26 - Oct 27
Total with taxes and fees
Cozy studio in Andersonville Chicago
A hotel room with a bed, a view of a cityscape, and a window with curtains.

8. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
$223 nightly
The price is $268
Oct 5 - Oct 6
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

10. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
$458 nightly
The price is $557
Oct 5 - Oct 6
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

11. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Downtown Evanston
10.0 out of 10, Exceptional, (37 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
$371 nightly
The price is $421
Oct 4 - Oct 5
Total with taxes and fees
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

12. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
$73 nightly
The price is $83
Oct 4 - Oct 5
Total with taxes and fees
King Bed Non-Smoking
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

13. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (18 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
$362 nightly
The price is $411
Oct 6 - Oct 7
Total with taxes and fees
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

14. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (7 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$255 nightly
The price is $302
Oct 26 - Oct 27
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
A courtyard with a garden, stone building, and wooden house.

15. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (109 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
$278 nightly
The price is $343
Oct 5 - Oct 6
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

16. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$246 nightly
The price is $253
Oct 13 - Oct 14
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern bedroom with a bed, a window, and a view of an outdoor area.

17. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (26 reviews)
"We had a great time it was an awesome place and we would definitely stay there again! The host was great the place was well equipped and in a great location for us!!"
United States
Wendy T.
$409 nightly
The price is $503
Oct 6 - Oct 7
Total with taxes and fees
The Lincoln Square Hideaway
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

18. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
$318 nightly
The price is $393
Oct 6 - Oct 7
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

19. Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.4 out of 10, Good, (16 reviews)
"Great location near university, the lake and public transportation. Felt safe in this area. Room was as described but could certainly use some updates and maintenance."
United States
Kevin G.
$341 nightly
The price is $421
Oct 15 - Oct 16
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
A living room with a green sofa, a dark armchair, a coffee table, two lamps, and a large abstract painting on the wall.

20. 1BR Well-Equipped Apartment

1BR Well-Equipped Apartment
Lakeview
8.4 out of 10, Very good, (11 reviews)
"Clean"
United States
Annette
$265 nightly
The price is $292
Oct 4 - Oct 5
Total with taxes and fees
1BR Well-Equipped Apartment
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

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Nice place! Perfect location!"
Franchisca 4-night trip
Posted 1 hour ago
Hampton Inn Chicago Downtown/Magnificent Mile

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 $83 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 North Shore Center for the Performing Arts, 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental near Skokie is located in the city center and has a balcony, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Skokie?

Expedia has 19 vacation rentals for your stay in Skokie.

What can I see and do in Skokie?

Family-friendly attractions include Adagio Teas, whereas Emily Oaks Nature Center is a spot to enjoy the outdoors. While in the area, you can also visit popular places like Wrigley Field and Navy Pier.

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.