Search vacation rental in Skokie, IL from 100+ sites!

127 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Skokie, IL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Skokie, IL

Top Vacation Rentals for Families in Skokie, IL

Make family travel to Skokie, IL seamless with spacious vacation rentals located just minutes from top city attractions.

Luxe Duplex-king Beds-gym-huge Backyard-game Room - Skokie, IL
9.7 78 reviews
Skokie, IL
07/04 – 07/18
$382/nighttotal: $5348 (14 )

Luxe Duplex-king Beds-gym-huge Backyard-game Room

1 5
apartment , Chicago
This 3-bedroom, 3-bathroom apartment is conveniently located on the Northwest side of Chicago, offering easy access to downtown and Rosemont, while being situated in a peaceful neighborhood. Guests consistently rate the apartment, location, and cleanliness as excellent.
This spacious home comfortably accommodates up to 7 guests and features a modern layout with an open-concept living area. Enjoy a fully equipped kitchen, a private gym, a large fenced-in backyard, and smart home technology, including high-speed internet and smart TVs in every room.
Parisian Inspired Escape - Close To Town & Nu - Skokie, IL
Skokie, IL
06/25 – 07/02
$571/nighttotal: $3997 (7 )

Parisian Inspired Escape - Close To Town & Nu

2 3
apartment , Evanston
This 2-bedroom rental unit is located in Evanston's Church & Dodge neighborhood, a half-mile from Downtown Evanston and less than a mile from Northwestern University.
This family-friendly apartment accommodates up to six guests and features a gourmet kitchen, a family room with a movie screen, an office, a patio, and is close to the beach, Lake Michigan, and various water and cycling activities.
Culinary Dream - Pizza Oven/bbq/smoker - Skokie, IL
9.9 81 reviews
Skokie, IL
06/25 – 07/02
$617/nighttotal: $4319 (7 )

Culinary Dream - Pizza Oven/bbq/smoker

1 3
apartment , Skokie
This Skokie apartment is located in a quiet and safe neighborhood, just a short drive from downtown Chicago and the North Shore. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment has three bedrooms and two bathrooms, allowing for a comfortable stay for up to ten guests. It features a modern kitchen with high-end appliances, a spacious living area, and a private driveway with ample parking.
The Avondale Retreat - Skokie, IL
Skokie, IL
06/25 – 07/02
$663/nighttotal: $4641 (7 )

The Avondale Retreat

3 3
apartment , Chicago
The Avondale Retreat apartment is located in Chicago's Avondale neighborhood, approximately 5-7 miles from attractions such as Lincoln Park Zoo, Wrigley Field, and the United Center, easily accessible by public transportation.
This 2400-square-foot, one-bedroom dwelling in Chicago boasts two bathrooms, accommodates up to 15 guests, and features a fully equipped kitchen, private balcony with garden views, free Wi-Fi, and parking.

Best Skokie, IL vacation rentals with parking

Exquisite Rogers Park 1 Bedroom, 1 Bath Apartment Near Evanston - Skokie, IL
8.2 5 reviews
Skokie, IL
06/27 – 07/04
$660/nighttotal: $4620 (7 )

Exquisite Rogers Park 1 Bedroom, 1 Bath Apartment Near Evanston

2 5
apartment , Chicago
This Rogers Park, Chicago rental is conveniently located 2.2 miles from Loyola University Chicago and offers easy access to public transportation, Lincoln Park Zoo (7.5 miles away), and Wrigley Field (5.3 miles away).
This 1000-square-foot one-bedroom, one-bathroom apartment features free Wi-Fi, private parking, a fully equipped kitchen, and a flat-screen TV with streaming services, comfortably accommodating two guests.
Fulton Market / Noble Square Free Parking, Laundry, 2.5 Miles To Mag Mile! - Skokie, IL
9.6 12 reviews
Skokie, IL
06/27 – 07/04
$568/nighttotal: $3976 (7 )

Fulton Market / Noble Square Free Parking, Laundry, 2.5 Miles To Mag Mile!

2 5
apartment , Chicago
This West Town Chicago apartment boasts easy access to the Blue Line, placing you within walking distance of Wicker Park and a short ride from the Magnificent Mile, United Center, and other major attractions.
The 900-square-foot rental features two bedrooms (one with a full-size bunk bed and trundle), one bathroom, sleeps six, includes in-unit laundry, and offers a fully equipped kitchen with a Keurig coffee maker.
Beautiful & Cozy 2bd/1b Near Ohare & Metra (Md-w) - Skokie, IL
9.7 98 reviews
Skokie, IL
06/27 – 07/04
$281/nighttotal: $1967 (7 )

Beautiful & Cozy 2bd/1b Near Ohare & Metra (Md-w)

2 2
apartment , Elmwood Park
This Elmwood Park apartment is conveniently located just over 2 miles from the Frank Lloyd Wright Historic District and 3.8 miles from the Ernest Hemingway Museum and House, offering easy access to these popular attractions. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, one-bathroom dwelling comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, a private fenced yard, a terrace or balcony, and access to a fitness center, garden, and parking.
Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar - Skokie, IL
10 11 reviews
Skokie, IL
06/27 – 07/04
$1408/nighttotal: $9856 (7 )

Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar

6 2
apartment , Chicago
This spacious six-bedroom, three-bathroom apartment in Chicago's peaceful Jefferson Park neighborhood is a short distance from downtown and O'Hare International Airport. With an excellent user rating, this 3200-square-foot apartment comfortably accommodates up to 16 guests.
The apartment features a speakeasy-style basement with a full bar, game room, and retro popcorn machine. There's also a large back deck with a grill, fire table, and picnic table, as well as multiple dedicated workspaces for remote work. The modern and spacious decor includes beautiful art and lush plants throughout, and high-quality mattresses, pillows, and linens ensure a restful night's sleep.

Frequently Asked Questions about vacation rentals in Skokie, IL

  • What are the top family-friendly attractions in Skokie, IL?

    The Skokie Park District offers a variety of family-friendly attractions, including the Skokie Lagoon, Oakton Park, and West Skokie Park. The Skokie Public Library also has a number of programs and events for families, such as story time and craft classes.
  • What are the best Airbnb and vacation rentals in Skokie, IL?

  • When is the best time to book a vacation rental in Skokie, IL?

    The best time to book a vacation rental in Skokie is during the shoulder seasons, from April to May and September to October. The weather is still pleasant during these months, and the crowds are smaller. You'll also find better deals on rental rates.
  • What are the most popular Airbnbs in Skokie, IL?

  • What are the best budget-friendly activities in Skokie, IL?

    Skokie has a lot of free activities, including walking or biking around the Skokie Lagoon, visiting the Skokie Public Library, and enjoying the parks. There are also several free concerts and events throughout the year.
  • What are the best vacation rentals with a pool in Skokie, IL?

  • What are the best restaurants with local dishes in Skokie, IL?

    Skokie has a diverse culinary scene, but some local favorites include The Skokie Inn, a classic diner serving American comfort food, and La Fiesta, a Mexican restaurant known for its authentic dishes.
  • What are the best rentals for families and kids in Skokie, IL?

  • What are the best walking or cycling routes in Skokie, IL?

    The Skokie Lagoon Trail is a popular walking and cycling route. It's a 3.5-mile paved trail that winds around the lagoon. There are also several other trails in the area, including the North Shore Channel Trail and the Skokie Valley Trail.
  • What are the best rentals or Airbnbs with a jacuzzi in Skokie, IL?

    Quiet And Welcoming House and Chateau Coco are the best vacation rentals or Airbnb with a jacuzzi in Skokie, IL.

  • Are there pet-friendly attractions in Skokie, IL?

    Many of Skokie's parks are pet-friendly, including Oakton Park and West Skokie Park. You can also bring your furry friend to the Skokie Lagoon, but be sure to keep them on a leash.
  • What are the benefits of choosing a vacation rental in Skokie, IL?

    Vacation rentals in Skokie offer more space and privacy than hotels. They also often come with amenities that are not typically found in hotels, such as kitchens and laundry facilities.
  • What are the top sports attractions and facilities in Skokie, IL?

    The Skokie Park District offers a variety of sports facilities, including Oakton Park and West Skokie Park. There are also several golf courses in the area, such as the Skokie Country Club.

Destinations nearby

Best Vacation Rentals with Balconies in Skokie, IL

Wake up to breathtaking views at these Skokie, IL vacation rentals with balconies, perfect for your morning coffee.

Wrigley 2br, 1ba With Free Parking - Skokie, IL
8.6 9 reviews
Skokie, IL
06/25 – 07/02
$893/nighttotal: $6251 (7 )

Wrigley 2br, 1ba With Free Parking

2 3
apartment , Chicago
This apartment is located in Chicago’s Wrigleyville neighborhood, just a short walk from Wrigley Field and a few miles from Lincoln Park Zoo. The area is known for its lively atmosphere, with plenty of bars and restaurants to explore. This 2-bedroom apartment offers 1250 square feet of space and comfortably accommodates up to 11 guests. The apartment features a fully equipped kitchen, a private patio with an outdoor fireplace, free parking, and other modern amenities for a comfortable and enjoyable stay.
Home Away From Home Unit. - Skokie, IL
Skokie, IL
06/27 – 07/04
$407/nighttotal: $2849 (7 )

Home Away From Home Unit.

3 2
apartment , Chicago
This 3-bedroom, 2-bathroom condo in Chicago's West Town neighborhood is located 1 mile from Millennium Park and Lake Michigan, and within 2 miles of the Field Museum of Natural History and the Museum of Science and Industry.
This residence accommodates up to 6 guests and offers amenities such as internet, air conditioning, a balcony, and parking, with convenient access to the United Center and Wrigley Field.
Modern 3br Apartment Near North Ave Shops - Skokie, IL
Skokie, IL
06/25 – 07/02
$458/nighttotal: $3206 (7 )

Modern 3br Apartment Near North Ave Shops

3 3
apartment , Chicago
This 3-bedroom, 2-bathroom apartment is located at the intersection of Chicago's Old Town, Lincoln Park, and Clybourn Corridor neighborhoods, offering immediate access to the New City shopping plaza and being minutes from the Second City Theater and the North Branch Trail leading to the lakefront.
This spacious 970 sq ft residence accommodates up to 8 guests with three king suites and an additional queen floor mattress, featuring a fully-equipped kitchen with stainless steel appliances, high-speed internet, air conditioning, and spectacular city views through large windows.
1br Near O'hare  Balcony  Workspace - Skokie, IL
Skokie, IL
06/25 – 07/02
$201/nighttotal: $1407 (7 )

1br Near O'hare Balcony Workspace

1 3
apartment , Chicago
This pet-friendly apartment in Cook County, Chicago, is located in the vicinity of O'Hare Airport and major highways, providing easy access to Allstate Arena and Norridge Park District.
This 600-square-foot dwelling offers one bedroom and one bathroom, accommodates up to three guests, and features a private balcony, a full kitchen with dining space for four, a dedicated workspace, and in-unit laundry, with private parking for one vehicle.

Best Skokie, IL vacation rentals with air conditioning

Townhouse In Rogers Park - Skokie, IL
9.0 4 reviews
Skokie, IL
06/27 – 07/04
$386/nighttotal: $2702 (7 )

Townhouse In Rogers Park

1 5
apartment , Chicago
This three-bedroom townhouse in a peaceful Chicago neighborhood offers easy access to beaches, restaurants, parks, and shopping, all within a 10-minute commute.
The fully furnished 3-bedroom, 1-bathroom property sleeps 5 guests and includes air conditioning, Wi-Fi, a full kitchen, and a private patio; registration number R24000118072 confirms compliance with local regulations.
Norwood Nook – 2br Near O’hare & Metra - Skokie, IL
9.8 60 reviews
Skokie, IL
06/25 – 07/02
$292/nighttotal: $2044 (7 )

Norwood Nook – 2br Near O’hare & Metra

1 3
apartment , Chicago
This Norwood Park apartment rental is ideally located near O'Hare International Airport (5 miles), the Norwood Park Metra station (0.5 miles), and Lutheran General Hospital (4.7 miles), offering easy access to both public transportation and major attractions.
This two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with quartz countertops, a work-from-home-friendly desk, blackout curtains, keypad entry, and on-site parking.
Old Irving Charm - Skokie, IL
10 41 reviews
Skokie, IL
07/04 – 07/18
$289/nighttotal: $4046 (14 )

Old Irving Charm

1 5
apartment , Chicago
This two-bedroom, one-bathroom apartment rental in Chicago's Montrose neighborhood is a 5-minute walk from the Montrose Blue Line station, providing easy access to downtown and a short drive to Millennium Park and O'Hare International Airport.
The unit sleeps five, features a kitchen with a refrigerator and microwave, air conditioning, and a garden, and is conveniently located near Old Irving Brewing Co.
Fully Furnished Rental In Old Town - 2 Beds - Unit 2r - Skokie, IL
8.8 5 reviews
Skokie, IL
07/04 – 07/18
$265/nighttotal: $3710 (14 )

Fully Furnished Rental In Old Town - 2 Beds - Unit 2r

2 5
apartment , Chicago
This Near North Side Chicago apartment is a short walk from Lincoln Park Zoo, Lake Michigan, and Michigan Avenue, offering convenient access to Sedgwick and Clark-Division public transportation stations.
This 950-square-foot rental boasts two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, in-unit laundry, and internet access.
©2026 cozycozy.com