Skokie holiday rentals

We found 2,000 holiday rentals — enter your dates for availability
Discover a selection of 19 homes, 15 apartments and other holiday rentals in Skokie that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Skokie

Showing deals for:25 Dec - 1 Jan

Private kitchen
Terrace/patio
Living area
Interior
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$21,406
for 7 nights, 1 apartment
AU$3,058 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Living area
Interior
Exterior
Private kitchen
Exceptional
(11 reviews)

NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!

Chicago

8% off
AU$12,072
for 7 nights, 1 home
AU$1,725 per night
includes taxes & fees
NEW! Large/Beautiful Home with 6BDS/4BTH + Garage!
Exterior
Dining
Private kitchen
Interior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

8% off
AU$6,145
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Interior
Cozy Home
Room
Private kitchen
Exceptional
(13 reviews)

Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking

Chicago

7% off
AU$4,941
for 7 nights, 1 home
AU$706 per night
includes taxes & fees
Spacious 4BR Near O’Hare & Rosemont Sleeps 8 / 2 Kitchens / Free Parking
Exterior
Living area
Interior
Living area
Exceptional
(34 reviews)

Roscoe Village | 8 Blocks to Wrigley

Chicago

7% off
AU$10,759
for 7 nights, 1 home
AU$1,537 per night
includes taxes & fees
Roscoe Village | 8 Blocks to Wrigley
Front Yard View
Living Room
Bedroom 1 (King Size) + 55Inch TV
Kitchen
Exceptional
(23 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$9,342
for 7 nights, 1 home
AU$1,335 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
Bedroom 3 w/ Queen Bed
Top floor kitchen and dining area
Kitchen on Top Floor
2 spots come with the unit- occupied by the van and SUV in this photo.
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$9,600
for 7 nights, 1 apartment
AU$1,371 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Bedroom 1 - King Bed
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$10,376
for 7 nights, 1 home
AU$1,482 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Private kitchen
Living area
Dining
Exterior
Exceptional
(114 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
AU$7,740
for 7 nights, 1 home
AU$1,106 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Dining room area
3 bedroom unit is top floor of historic greystone
Living room area
View of Robey Hotel from back deck
Exceptional
(100 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$8,329
for 7 nights, 1 home
AU$1,190 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Room
Interior
Interior
Dining
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
AU$11,032
for 7 nights, 1 home
AU$1,576 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Private kitchen
Living area
Dining
Living area
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,910
for 7 nights, 1 apartment
AU$701 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Interior
Private kitchen
Games room
Private kitchen
Exceptional
(6 reviews)

Old Irving Neighborhood | 20 Min Uber to Mag Mile

Chicago

7% off
AU$9,486
for 7 nights, 1 home
AU$1,355 per night
includes taxes & fees
Old Irving Neighborhood | 20 Min Uber to Mag Mile
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Kitchen (upstairs)
Exceptional
(99 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$13,423
for 7 nights, 1 apartment
AU$1,918 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Interior
Upon entering lobby there will be 2 doors. You have rented the apartment on the
This is the first room you will enter upon arriving safely inside.
View from sidewalk
Exceptional
(11 reviews)

5 bedroom with 5 beds and 2 bathrooms

Oak Park

12% off
AU$5,264
for 7 nights, 1 apartment
AU$752 per night
includes taxes & fees
5 bedroom with 5 beds and 2 bathrooms
Private kitchen
Interior
Dining
Room
Exceptional
(19 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$2,757
for 7 nights, 1 apartment
AU$394 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Interior
Interior
Living area
Room
Exceptional
(12 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$3,041
for 7 nights, 1 apartment
AU$434 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Living area
Interior
Room
Interior
Wonderful
(91 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,860
for 7 nights, 1 apartment
AU$266 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Living area
Dining
Living area
Room
Exceptional
(6 reviews)

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

Chicago

7% off
AU$11,602
for 7 nights, 1 apartment
AU$1,657 per night
includes taxes & fees
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Games room
Living area
Games room
Room
Exceptional
(9 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

7% off
AU$11,247
for 7 nights, 1 apartment
AU$1,607 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Living area
Belmont Harbor
Exterior
Private kitchen
Exceptional
(193 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

15% off
AU$8,598
for 7 nights, 1 home
AU$1,228 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Room
Exterior
Private kitchen
Dining
Exceptional
(36 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,843
for 7 nights, 1 apartment
AU$1,263 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Bedroom 1 (with Desk)
Side stairwell to Entrance of Unit (see red umbrella on deck)
Private Patio
Living Room
Exceptional
(39 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

9% off
AU$4,206
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Private kitchen
Room
Exterior detail
Room
Wonderful
(17 reviews)

Modern Deluxe Studio Suite in lovely Oak Park!

Oak Park

7% off
AU$1,718
for 7 nights, 1 apartment
AU$245 per night
includes taxes & fees
Modern Deluxe Studio Suite in lovely Oak Park!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The friendly area of Skokie awaits your stay

The gardens and other outdoor surroundings create an inviting atmosphere in Skokie. This welcoming city is known for its shopping, restaurants and sporting events. Wrigley Field and Navy Pier are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Skokie

Are you searching for top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Skokie a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Glen Club (6 mi / 9.6 km)
  • The Dome at the Parkway Bank Sports Complex (7.7 mi / 12.3 km)
  • Northbrook Sports Complex (8.3 mi / 13.3 km)
  • Lincoln Park Zoo (9.5 mi / 15.3 km)
  • Chevy Chase Country Club (12.6 mi / 20.2 km)
  • LEGOLAND® Discovery Center (15 mi / 24.2 km)

Exploring the natural landscape of Skokie

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Skokie. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (12 mi / 19.3 km)
  • Grant Park (12.6 mi / 20.3 km)
  • North Shore Beach Park (4.8 mi / 7.7 km)
  • Portage Park (5.5 mi / 8.8 km)
  • Montrose Beach (7 mi / 11.2 km)
  • Lincoln Park (8 mi / 13 km)

Transport options to and around Skokie

The nearest airport is in Chicago O'Hare International Airport (ORD), located 9.2 mi (14.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago, IL (PWK-Chicago Executive), which is 10 mi (16 km) away.

Frequently asked questions

What is the best area to stay in Skokie when booking a holiday rental?
When considering a holiday rental in Skokie, Illinois, a popular area to stay is near the downtown district. This vibrant neighbourhood offers a range of properties, making it an ideal choice for visitors seeking convenience and accessibility. Here, you'll find a delightful mix of shops, restaurants, and cafes, great for enjoying local cuisine and culture.Another appealing area is around the North Shore Centre for the Performing Arts, which not only provides a fantastic venue for various performances but also places you near the scenic Skokie Lagoons. These lagoons are great for outdoor activities like walking, biking, or simply enjoying a picnic by the water.
What is the most popular type of holiday rental accomodation in Skokie?
In Skokie, holiday houses are the most popular type of holiday rental, with approximately 100 available across the area. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a homely atmosphere. Many holiday houses also include outdoor spaces, such as gardens or patios, where guests can relax. Additionally, there are around 48 apartments for those preferring a more compact living arrangement, typically equipped with modern amenities. A few condos and cottages are also scattered throughout Skokie, providing additional options for travellers.
Are there any family house rentals in Skokie?
In Skokie, Illinois, families will find a variety of holiday rentals—there are 16 available throughout the area. This suburb offers spacious properties that cater to groups, often featuring multiple bedrooms and ample living space for everyone to unwind. Many homes include fully equipped kitchens, allowing for family meals, and some even have outdoor patios or gardens where children can play.The locale is conveniently situated near parks, such as the popular Niles West Park, which offers playgrounds and sports facilities. Additionally, visitors can enjoy nearby attractions like the Skokie Northshore Sculpture Park, superb for a leisurely stroll and appreciating art in an outdoor setting.
Can I rent a holiday home with a pool or hot tub in Skokie?
In Skokie, there are several holiday homes available for rent that feature pools and hot tubs. This suburban area, located just north of Chicago, offers a variety of neighbourhoods where these properties can be found, including the family-friendly areas near Skokie Northshore Sculpture Park and the vibrant downtown section.Travellers can expect amenities such as private pools, inviting hot tubs, and spacious outdoor areas for relaxation. Many rentals also come with fully equipped kitchens, allowing guests to prepare meals at their convenience. Some properties may feature additional luxuries like outdoor dining spaces and well-maintained gardens, making them great for family gatherings or get-togethers with friends.
Are there pet-friendly house rentals in Skokie?
In Skokie, there are several pet-friendly house rentals available, with around 17 options to choose from. Many of these properties come equipped with modern amenities such as spacious gardens, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups travelling with pets.Skokie is home to several parks that are great for pet owners, including the expansive Emily Oaks Nature Centre, which features walking trails and natural habitats for outdoor exploration. Additionally, the nearby Skokie Northshore Sculpture Park offers picturesque paths for leisurely strolls with pets, as well as a unique outdoor art experience.
Are there any remote work holiday rentals in Skokie?
In Skokie, Illinois, there are numerous options for remote work holiday rentals, with around 156 available throughout the area. This suburb of Chicago offers a convenient setting for those looking to combine work and leisure. Many properties are equipped with amenities tailored for remote work, including high-speed internet and dedicated office spaces, ensuring a productive environment.Travellers can expect a variety of accommodations, from modern apartments to spacious homes, often featuring comfortable living areas, full kitchens for meal preparation, and Wi-Fi access. Skokie is also home to several parks, shopping centres, and dining options, providing a pleasant atmosphere for both work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Skokie?
In Skokie, popular rental amenities primarily include kitchens, which allow guests to prepare their own meals, along with coffee and tea makers for that essential morning boost. Many properties also offer onsite parking, making it convenient for those travelling by car. Additionally, rentals often permit pets, accommodating travellers who wish to bring their furry companions along. Service animals are also welcomed, ensuring a comfortable stay for all guests.
When is the best time to visit Skokie for a holiday rental?
The peak season for visiting Skokie is during the summer months of June to August, with July being the most popular month for holiday rentals. This vibrant time of year invites travellers to take advantage of the warm weather while exploring local parks, enjoying outdoor festivals, and indulging in the diverse culinary scene that Skokie has to offer.With temperatures typically ranging from the mid-teens to the low 30s Celsius, visitors can comfortably enjoy outdoor activities such as picnics in central parks or leisurely strolls along the area's scenic walking paths. The lively option during these months also means you'll have easy access to community events and entertainment options, making it a great time to immerse yourself in local culture.If you're considering a more budget-friendly option, the low season in December presents an opportunity to experience Skokie's charm during the festive season. While temperatures can drop to around freezing, this month offers a unique perspective on the area, with holiday lights and decorations creating a warm and inviting atmosphere.Ultimately, the best time to book a holiday rental in Skokie depends on your preference for vibrant summer activities or the quieter, festive charm of winter.
What are the top attractions in Skokie?
In Skokie, visitors can enjoy a variety of attractions that highlight both culture and nature. The Skokie Northshore Sculpture Park is a popular outdoor space that features a stunning collection of sculptures along the greenbelt, superb for a leisurely stroll. The park runs alongside the North Shore Channel and provides beautiful views, making it a great spot for outdoor enthusiasts.Another key attraction is the Skokie Theatre, which hosts a range of performances and events, providing insight into the local arts scene. For families, the Skokie Public Library is a significant community hub, offering various programmes and activities for all ages, along with a well-stocked collection that reflects the community's diverse interests.Additionally, the nearby Old Orchard Shopping Centre offers a mix of shopping, dining, and entertainment options, making it a popular destination for both locals and visitors. For those interested in history, the Skokie Heritage Museum provides insight into the town's past and its cultural evolution.
Are all fees included in the Skokie holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Skokie holiday homes with parking?
Stayz offers a wide selection of holiday homes in Skokie with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Skokie holiday homes?
You can find great discounts on holiday homes in Skokie on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Skokie holiday home booking on Stayz?
To find Skokie holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Skokie?
A long-stay holiday home in Skokie is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Skokie holiday home?
Book your Skokie holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Skokie?
Prices for holiday homes in Skokie vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Skokie to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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