Skokie Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Skokie vacation 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, (36 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
$626 nightly
The price is $669
May 11 - May 12
Total with taxes and fees
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Dining

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.
$193 nightly
The price is $212
May 26 - May 27
Total with taxes and fees
1-Bedroom Pad | Cozy + All-Set
Iron/ironing board, travel crib, WiFi, bed sheets

Chic Skokie Retreat - 1BR Unit in Skokie

Chic Skokie Retreat - 1BR Unit in Skokie
Skokie
10.0 out of 10, Exceptional, (1 review)
$189 nightly
The price is $207
May 19 - May 20
Total with taxes and fees
Chic Skokie Retreat - 1BR Unit in Skokie
TV, offices

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.
$268 nightly
The price is $296
May 18 - May 19
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
Fridge, microwave, oven, stovetop

Skokie 1BR Stay Near Parks, Dining & Transit

Skokie 1BR Stay Near Parks, Dining & Transit
Skokie
$193 nightly
The price is $212
May 10 - May 11
Total with taxes and fees
Skokie 1BR Stay Near Parks, Dining & Transit
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
$528 nightly
The price is $581
May 20 - May 21
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
$231 nightly
The price is $260
May 26 - May 27
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"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.
$278 nightly
The price is $316
May 10 - May 11
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$531 nightly
The price is $608
May 26 - May 27
Total with taxes and fees
River North Rooftop With In and Out Parking 3
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.
$373 nightly
The price is $399
May 4 - May 5
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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, (99 reviews)
"Everything was good!"
United States
Brio
$247 nightly
The price is $283
May 5 - May 6
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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.
$449 nightly
The price is $554
May 6 - May 7
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"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
$226 nightly
The price is $256
Jun 3 - Jun 4
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
TV, offices

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.6 out of 10, Exceptional, (27 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
United States
shayna j.
$695 nightly
The price is $858
May 7 - May 8
Total with taxes and fees
3BR Luxury Suite w/Gym and Balcony
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
$438 nightly
The price is $501
May 4 - May 5
Total with taxes and fees
Oak Park Victorian by FLW Studio
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$236 nightly
The price is $279
May 7 - May 8
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$277 nightly
The price is $314
May 10 - May 11
Total with taxes and fees
West Loop Living – Bright 1BR
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$399 nightly
The price is $492
May 20 - May 21
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (20 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
$253 nightly
The price is $284
May 12 - May 13
Total with taxes and fees
Cozy & Furnished 2BR Unit
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,148 reviews)
"Thank you for the stay"
United States
Marco
$174 nightly
The price is $204
May 11 - May 12
Total with taxes and fees
Sentral Michigan Avenue
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

Freehand Chicago

Freehand Chicago

8/10 Good
"Clean room, looks older, bed was comfortable."
William C 1-night trip
Posted 1 hour ago
Freehand Chicago

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 $164 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental near Skokie is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 25 vacation 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 family-friendly sights, whereas cultural attractions include Skokie Theatre. 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.