Skokie vacation rentals

We found 2,100 vacation rentals — enter your dates for availability

Discover a selection of 22 homes, 11 apartments, and other vacation rentals in Skokie that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include parking and a pool. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Skokie

Showing deals for:Nov 14 - Nov 21

Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Interior
9.2 out of 10 rating
Wonderful
(50 reviews)

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Chicago, IL

18% off
Price is CA $249
CA $2,567 total
includes taxes & fees
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

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Find out more about Skokie

Find out more about Skokie

Why visit Skokie

  1. Family-Friendly Attractions: Skokie offers numerous activities suitable for families, ensuring a fun-filled vacation for all ages.
  2. Beautiful Urban Parks: Explore expansive parks that provide opportunities for outdoor recreation and relaxation amidst nature.
  3. Cultural Experiences: Experience local culture in nearby Prospect Heights, known for its friendly atmosphere and romantic vibe.
  4. Scenic South Lakefront: Enjoy the picturesque beauty of the south lakefront, perfect for scenic walks and leisure activities.
  5. Diverse Accommodation Options: Choose from a variety of vacation rentals, including cozy apartments and spacious homes, tailored to your needs.

Popular types of accommodation in Skokie

If you're exploring vacation rentals in Skokie, you're in for a treat! Our platform offers a variety of popular accommodations, including apartments, houses, and condos. Whether you're searching for a cozy one-bedroom apartment in Skokie or looking for apartment rentals near Skokie, we provide transparent information to help you find the perfect stay. Enjoy savings and reassurance as you plan your getaway!

  • Apartments: The top choice for visitors to Skokie, offering comfortable living spaces suitable for singles, couples, or families.
  • Houses: A popular second option, these homes provide a homey atmosphere for larger groups or families seeking privacy.
  • Condos: A third favourite, condos in Skokie combine modern amenities with a convenient location.
  • Cottages: Fourth on the list, these quaint lodgings offer a charming escape for couples or small families.
  • Resorts: Rounding out the list, resorts provide a luxurious experience with various leisure activities.**

Top attractions in Skokie

Skokie, Illinois, is an ideal destination for families and urban explorers alike, offering a mix of cultural attractions and outdoor activities. Visitors can enjoy beautiful beaches, modern colleges and universities, and expansive urban parks. Whether you're seeking a family-friendly experience or a taste of local culture, Skokie has something for everyone, making it a perfect spot for a memorable vacation.

  1. Northwestern University: This modern university, located 6.4km from Skokie, boasts a vibrant campus with stunning architecture, art installations, and bustling student life, providing an energizing city atmosphere.
  2. Donald E. Stephens Convention Center: Situated 11.3km away, this premier event venue is perfect for conferences and conventions, exuding a professional ambiance ideal for business networking and exhibitions.
  3. Portage Park: Located 8.0km from Skokie, this urban park offers a family-friendly environment with playgrounds, walking paths, and green spaces, making it a lovely outdoor retreat in a city setting.

Things to do recommended for couples

For a romantic getaway in Skokie, consider an enchanting concert at Aragon Ballroom, a unique dinner at Schaumburg Medieval Times, or a delightful wine tasting at Lynfred Winery. Each offers a charming atmosphere perfect for couples looking to create lasting memories together.

Things to do recommended for families

In Skokie, families can soak up the sports atmosphere at Wrigley Field, enjoy thrilling adventures at Sky High Sports Niles, or unwind at the serene Norridge Park District. Each location offers unique experiences perfect for family bonding and creating lasting memories.

Things to do recommended for groups

Experience the excitement at Rivers Casino for a lively night out or enjoy a captivating performance at Rosemont Theatre, perfect for families. Don't miss shopping at the Fashion Outlets of Chicago, where you can find great deals and entertainment options for everyone in your group.

What do I need to keep in mind when booking a vacation in Skokie

When planning your trip—whether with friends, family, pets, or for an extended stay—it's important to prioritize your preferences in your searches. Here are some helpful Vrbo booking tips tailored for you.

  • Traveling to Skokie with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Skokie with young kids: Traveling with young children can be a bit of a challenge. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Skokie: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Skokie: If you're in search of vacation rentals offering great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Skokie

Skokie, Illinois, offers a delightful blend of family-friendly attractions and vibrant urban experiences. Explore its charming residential areas, enjoy the scenic beauty of the south lakefront, and discover budget-friendly options alongside priciest neighbourhoods. For a taste of local culture, visit nearby Prospect Heights, where friendly people and a romantic atmosphere await. Whether you're seeking outdoor adventures or a bustling city vibe, Skokie is the perfect base for your vacation explorations.

  • Lincolnwood: Located a mere 3.2km from Skokie, Lincolnwood is a charming city that offers a delightful blend of family-friendly activities and urban experiences. Visitors can enjoy a variety of outdoor spaces and community events, making it perfect for those seeking relaxation or recreation. Lincolnwood boasts several educational institutions, theatres, and music venues, ensuring there's always something happening. Notable landmarks include modern college facilities and sports stadiums, making it an attractive spot for sports enthusiasts and culture lovers alike.
  • Morton Grove: Also situated 3.2km from Skokie, Morton Grove is a vibrant city that caters to family outings and urban exploration. The area is known for its accessible shopping areas and diverse entertainment options, including theatres that showcase local talent. Morton Grove provides ample outdoor experiences, with parks and recreational facilities for visitors of all ages. Key attractions include modern college campuses and sports facilities, making it a great destination for both leisure and educational pursuits.
  • Evanston: Just 4.8km from Skokie, Evanston is a dynamic city with a rich cultural scene and a strong sense of community. Known for its beautiful lakefront and outdoor activities, Evanston is perfect for those who enjoy nature alongside city life. The city features a variety of shopping areas and hosts numerous music concerts throughout the year. Landmark attractions include prestigious universities and sports facilities, ensuring that visitors can immerse themselves in both education and entertainment while exploring the vibrant local scene.

Best time to go to Skokie

If you're planning a trip to Skokie, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.2°F (-3.8°C)Light RainMostly CloudySlightly LowSlightly Low
February26.4°F (-3.1°C)Light RainMostly CloudyAverageSlightly Low
March36.7°F (2.6°C)Light RainMostly CloudyAverageSlightly Low
April45.3°F (7.4°C)Light RainMostly CloudySlightly HighAverage
May56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
June66.9°F (19.4°C)Light RainMostly SunnySlightly HighSlightly High
July73.2°F (22.9°C)Light RainMostly SunnySlightly HighSlightly High
August72.9°F (22.7°C)Light RainMostly SunnyAverageSlightly High
September66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
October54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
November41.9°F (5.5°C)Light RainMostly SunnySlightly LowAverage
December32.5°F (0.3°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Consider being flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your journey!

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, and manage your travel arrangements with ease. You can easily access properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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 Michigan Avenue are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Skokie

Do you want to discover attractions to visit during your stay? Venture out of your vacation home and experience everything that makes Skokie a fun spot to vacation. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • The Glen Club (6 mi / 9.6 km)
  • Lincoln Park Zoo (9.5 mi / 15.3 km)
  • Dave & Buster's (10.7 mi / 17.2 km)
  • Chevy Chase Country Club (12.6 mi / 20.2 km)
  • LEGOLAND® Discovery Center (15 mi / 24.2 km)
  • Conway Farms Golf Club (15.8 mi / 25.4 km)

Exploring the natural landscape of Skokie

Whether you're an active traveler or just want to take in the scenery, Skokie is a great place to spend some time outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Kathy Osterman Beach (5.6 mi / 9 km)
  • Montrose Beach (7 mi / 11.2 km)

Transportation options to and around Skokie

The nearest airport is in Chicago O'Hare Intl. Airport (ORD), located 9.2 mi (14.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly 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 vacation rental?
When considering a vacation rental in Skokie, Illinois, the best area to stay is the neighbourhood surrounding Old Orchard. This vibrant area is not only home to the renowned Westfield Old Orchard shopping centre, which boasts a variety of shops, dining options, and entertainment, but it also offers a delightful blend of urban convenience and suburban charm. The shopping centre is a major draw for visitors, providing access to both high-end retailers and popular brands.

Another appealing neighbourhood is the Skokie Village Centre, which features a lovely mix of parks, cultural attractions, and local eateries. This area is particularly close to the Skokie Public Library, a cultural hub that hosts various events and programmes throughout the year. The proximity to parks like the beautiful Skokie Northshore Sculpture Park enhances the overall experience, offering lovely trails for walking and cycling, as well as an impressive outdoor art installation.
How much does it cost to rent a vacation home in Skokie?
Prices for vacation rentals 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. Vrbo offers something for every taste and budget, from affordable rentals in Skokie to more spacious homes.
Are there any discounts for Skokie vacation house rentals?
You can find great discounts on house rentals in Skokie on Vrbo, 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.
Where are the best areas for renting a beach house in Skokie?
For renting a beach house in Skokie, Illinois, travellers should consider the nearby areas along Lake Michigan, particularly in the adjacent towns of Evanston and Wilmette. The shoreline in these locations offers picturesque views and convenient access to sandy beaches. In Evanston, the area around Lee Street Beach is particularly appealing, where beach houses often come equipped with outdoor spaces such as patios or balconies, great for enjoying the summer sun. Many properties also feature modern amenities like fully equipped kitchens and spacious living areas, making them suitable for families or groups.

In Wilmette, the beaches near Gillson Park provide additional options, where you can find charming beach houses that often include amenities like private decks and gardens, ideal for relaxing after a day at the beach. This area offers a serene environment with easy access to local shops and restaurants, enhancing the overall experience for travellers.
What is the most popular type of vacation rental accomodation in Skokie?
In Skokie, vacation houses are the most popular type of rental, with around 22 available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor spaces, such as gardens or patios, great for relaxing after a day of exploring nearby attractions like the Skokie Northshore Sculpture Park or the Illinois Science and Technology Park. Additionally, there are about 10 apartments and several condos available, which provide a more compact option for travellers looking for convenience and comfort.
Are there any family house rentals in Skokie?
In Skokie, Illinois, there are numerous family-friendly house rentals available, with around 17 options to choose from. This suburban area is well-suited for families, offering spacious homes equipped with essential amenities like full kitchens, ample living spaces, and outdoor areas for children to play. Many properties also feature conveniences such as air conditioning and Wi-Fi, ensuring a comfortable stay for all guests.
Can I rent a vacation home with a pool or hot tub in Skokie?
In Skokie, there are several vacation homes available for rent that feature pools and hot tubs, making it a great option for those looking to enjoy some relaxation during their stay. This suburban area near Chicago offers a mix of residential neighbourhoods, where travellers can find properties with amenities suited for families or groups. Many rentals include private pools, spacious outdoor areas, and hot tubs, ideal for unwinding after a busy day exploring the local attractions.
Can I find long-stay vacation rentals in Skokie?
A long-stay vacation rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Skokie?
In Skokie, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these homes are equipped with modern amenities such as spacious living areas, updated kitchens, and private outdoor spaces, making them suitable for both relaxation and entertaining.
Are there any remote work vacation rentals in Skokie?
In Skokie, Illinois, there are several remote work vacation rentals available, with around 36 options to choose from. This suburban area is well-suited for those looking to combine work and leisure, providing a peaceful environment while remaining close to the vibrant city of Chicago. Many of the properties come equipped with essential remote work amenities, including dedicated office spaces, desks, computer monitors, and high-speed Wi-Fi, ensuring a productive work-from-home experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Skokie vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals 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 on Vrbo 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.
What are popular rental amenities in Skokie?
In Skokie, popular rental amenities primarily include kitchens equipped with stovetops, microwaves, and essential cookware, dishware, and utensils, making it convenient for guests to prepare their own meals. Additionally, many rentals offer complimentary Wi-Fi, allowing travellers to stay connected during their stay. These amenities cater well to families and groups looking for a comfortable, self-sufficient experience in the area.
When is the best time to visit Skokie for a vacation rental?
The best time to visit Skokie for a vacation rental is during the vibrant summer months, particularly in July. This period is part of the peak season, running from June to August, when the weather is warm and inviting, making it ideal for outdoor activities and family adventures. Visitors can enjoy a variety of local festivals, outdoor dining, and the lush parks that Skokie has to offer.

Throughout July, temperatures typically hover around the mid-20s Celsius, creating a pleasant environment for exploring the area's attractions, such as the Skokie Northshore Sculpture Park and the nearby beaches of Lake Michigan. The lively atmosphere during this time is superb for those looking to connect with fellow travellers and immerse themselves in community events.

For those seeking a more budget-friendly experience, consider planning your visit in December. While this month falls outside the peak season, it offers a unique charm with festive vacation decorations and a peaceful ambiance. You can enjoy the local winter festivities without the hustle and bustle of larger crowds.
How early should I book a Skokie vacation rental?
Book your Skokie vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Skokie?
In Skokie, visitors can explore several noteworthy attractions that showcase the area's cultural and recreational offerings. The Illinois Holocaust Museum & Education Centre is a significant site, providing profound insights through its exhibitions and memorials. The museum is located near the central part of Skokie, making it easily accessible from various neighbourhoods.

For those who enjoy the outdoors, the Skokie Northshore Sculpture Park offers a delightful experience along the scenic North Shore Channel, featuring a collection of contemporary sculptures set against a beautiful backdrop. Additionally, the nearby Skokie Park District boasts numerous parks and recreational facilities, including the popular Emily Oaks Nature Centre, which offers nature trails and educational programs.
Can I change or cancel my Skokie home rental booking on Vrbo?
To find Skokie vacation rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Skokie vacation rental prices shown on Vrbo?
Vrbo 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.

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