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Best Vacation rentals and Airbnb offers in Oak Park, IL
10 21 reviews
Oak Park, IL
06/28 – 07/05
$302/nighttotal: $2114 (7 )
Convenient/private/spacious In Chicago By Oak Park
1 5
apartment , Chicago
This family-friendly apartment in Chicago offers a prime location, a 5-minute drive from Oak Park attractions like the Hemingway Museum and Frank Lloyd Wright Homes, with the Eisenhower Expressway and CTA Blue Line just 2 minutes away for under a 15-minute drive to downtown Chicago. This 3-bedroom, 1-bathroom unit accommodates up to 7 guests, featuring air conditioning, a full kitchen with a fridge, freezer, and microwave, a 65" TV with Samsung TV Plus, and access to a backyard with a picnic table, all accessible via keyless entry with free street parking and one daily overnight permit.
9.7 435 reviews
Oak Park, IL
10/11 – 10/21
$200/nighttotal: $2000 (10 )
The Avondale Lower Level
2 2
apartment , Chicago
This garden apartment is located in Chicago's Irving Park neighborhood, just a short distance from Wrigley Field and downtown. The area offers a mix of residential charm and local eateries, providing a relaxed atmosphere for your stay. This apartment consistently receives excellent ratings for cleanliness, location, and overall experience. The apartment features two bedrooms and one bathroom, offering 1,000 square feet of space and accommodating up to four guests. It comes equipped with a full kitchen, laundry facilities, a private garden, and free parking, making it a comfortable and convenient base for exploring Chicago.
9.8 139 reviews
Oak Park, IL
10/11 – 10/21
$201/nighttotal: $2010 (10 )
Cheerful Remodel Prime Location
1 2
apartment , Oak Park
This Oak Park apartment rental is conveniently located one block from the Green Line, offering easy access to downtown Chicago and a short walk to Whole Foods, Trader Joe's, and Oak Park's downtown area. The one-bedroom, one-bathroom unit sleeps two guests and includes on-site parking, air conditioning, internet, and a fully equipped kitchen; enjoy nearby shops, restaurants, and cultural attractions.
9.1 620 reviews
Oak Park, IL
09/06 – 09/07
$925/nightfor 1 night
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2br Apts
2 2
apartment , Chicago
This apartment is located in the Lakeview neighborhood, just a 2-minute walk from Wrigley Field and a short drive from Lincoln Park Zoo, offering easy access to Chicago's vibrant attractions. It boasts very good user ratings, an excellent location rating, and a very good cleanliness rating. This 2-bedroom, 1-bathroom unit features a fully equipped kitchen, a private balcony, and free Wi-Fi. Enjoy the convenience of on-site parking, air conditioning, and a garden area, making it a comfortable and convenient choice for your Chicago stay.
10 12 reviews
Oak Park, IL
06/25 – 07/25
$176/nighttotal: $5280 (30 )
Top Floor Irving Park Chicago Great Location!
1 3
apartment , Chicago
This newly remodeled, top-floor condo is located in Chicago's Irving Park neighborhood, offering a peaceful and centrally-located base for exploring the city's attractions. This 2-bedroom, 1-bathroom residence accommodates up to 4 guests and features air conditioning, internet, and a kitchen, with access to a shared backyard in a quiet building.
9.7 126 reviews
Oak Park, IL
06/25 – 07/25
$182/nighttotal: $5460 (30 )
Spaulding Oasis On 4 Lots In Humboldt Park!
1 3
apartment , Chicago
This Chicago apartment is located in a quiet, residential neighborhood, perfect for those seeking a peaceful escape from the city. It has received excellent ratings for its cleanliness, location, and overall experience. The rental has two bedrooms and one bathroom, comfortably accommodating up to five guests. It boasts a spacious backyard with a garden, perfect for relaxing, entertaining, or hosting small events. The apartment comes fully equipped with modern amenities, including a kitchen with a dishwasher, a smart TV, and a comfortable couch bed.
9.8 152 reviews
Oak Park, IL
07/10 – 07/12
$3800/nighttotal: $7600 (2 )
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
6 14
apartment , Chicago
Loft606 Chicago is a 5,307 sq. ft. loft located in the heart of Chicago's Wicker Park neighborhood, just a short walk from the 606 Bloomingdale Trail and the Blue Line CTA station. With excellent user, location, and cleanliness ratings, this apartment offers a unique and appealing experience for guests visiting Chicago. The apartment features a massive open space with a 26' timber beamed ceiling and skylights, accommodating up to 20+ guests with 7 bedrooms, 11 beds, and 2 large couches. Guests can enjoy a state-of-the-art gourmet kitchen, full-size bar, fireplace, and sound system, as well as a garden patio and rooftop deck for outdoor relaxation. The apartment also includes a fitness center, tennis court, spa, and three off-street parking spots.
9.4 71 reviews
Oak Park, IL
07/17 – 07/27
$265/nighttotal: $2650 (10 )
Mins To Dt & Frank Lloyd Wright
1 1
apartment , Oak Park
This Oak Park studio apartment is ideally located near Petersen's Ice Cream and Broken Tart, a short walk from Frank Lloyd Wright's Home and Studio, and a 10-minute walk from downtown Oak Park. The one-bedroom, one-bathroom unit sleeps three guests and includes a kitchen with a refrigerator, freezer, and microwave, plus air conditioning, internet, parking, and a garden; enjoy easy access to Giordano's and other nearby restaurants.
9.7 387 reviews
Oak Park, IL
06/28 – 07/03
$194/nighttotal: $970 (5 )
Small But Mighty 700 Sqft Cottage Apt (1br/1ba)
1 2
apartment , Oak Park
This ground-floor apartment in Oak Park is a short walk from the Blue Line Station and a quick drive to downtown Chicago, making it a perfect base for exploring the area. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The two-bedroom apartment comfortably accommodates up to four guests, perfect for families or small groups. You'll find a fully equipped kitchen, washer and dryer, high-speed internet, and a private garage, along with a pack-and-play for families with young children, ensuring a convenient and enjoyable stay.
9.8 18 reviews
Oak Park, IL
09/06 – 09/07
$681/nightfor 1 night
Chic 3bed 2bath Home With Free Parking Close To United Center
3 2
apartment , Oak Park
This Oak Park family home, located within three miles of the Frank Lloyd Wright Historic District and Concordia University Chicago, offers easy access to major attractions and public transportation (Austin Station is a 12-minute walk). The 1500-square-foot house features three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, free Wi-Fi, a private fenced yard, and air conditioning.
9.9 88 reviews
Oak Park, IL
07/17 – 07/27
$385/nighttotal: $3850 (10 )
Appartement-d'exception-salle De Bain Privée-vue S
3 1
apartment , Oak Park
This three-bedroom apartment is located in Historic Oak Park, just three blocks from the L-line, next to Hemingway's birthplace, and within walking distance of Frank Lloyd Wright studios. The apartment has received excellent user, location, and cleanliness ratings. The 1,800 square foot apartment can accommodate up to six guests with a spacious dining room, living room, top-of-the-line kitchen, generous office space, and inviting TV room. The apartment also offers amenities like air conditioning, a garden, parking, high-speed internet, and two garages.
9.8 20 reviews
Oak Park, IL
10/11 – 10/21
$475/nighttotal: $4750 (10 )
Oak Park Home W/ Grill - 5 Mi To Garfield Park!
3 2
apartment , Oak Park
This vacation home is located in Oak Park's Frank Lloyd Wright Historic District, just a short walk from the Ernest Hemingway Museum and House and the heart of the area. It has received excellent user ratings, making it a popular choice for travelers. The home has 3 bedrooms and 1 bathroom, offering enough space for up to 6 guests. It includes modern amenities like air conditioning, internet access, a fully equipped kitchen, and parking, making it comfortable and convenient for any traveler.
Compare Vacation Rentals for Families in Oak Park, IL
These family-friendly vacation rentals in Oak Park, IL offer spacious layouts and easy access to top city attractions.
9.7 98 reviews
Oak Park, IL
06/25 – 07/25
$201/nighttotal: $6030 (30 )
Beautiful & Cozy 2bd/1b Near Ohare & Metra (Md-w)
1 3
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.
8.0 1 review
Oak Park, IL
06/28 – 07/05
$384/nighttotal: $2688 (7 )
Secret Gallery On The Park - 2bd/1ba
2 5
apartment , Chicago
This 2-bedroom rental is in a prime Chicago district, 0.9 miles from the city center, offering an 18-minute walk to Oak Street Beach and proximity to attractions like Willis Tower. This 860-square-foot flat accommodates up to 6 guests and features a private balcony with city views, air conditioning, complimentary WiFi, and a fully equipped kitchen, with easy access to shopping and entertainment.
8.2 35 reviews
Oak Park, IL
09/06 – 09/07
$295/nightfor 1 night
Bright Garden Studio
1 2
studio , Evanston
This Evanston studio apartment is located in a quiet, family-friendly upper-middle-class neighborhood with easy access to CTA bus and train lines, providing convenient transportation to downtown Chicago and its attractions like the Art Institute and Navy Pier. The 800-square-foot unit features one bedroom, one bathroom, and accommodates up to four guests, boasting amenities such as a full kitchen with dishwasher, in-unit laundry, a Jacuzzi, and a private garden.
9.4 3 reviews
Oak Park, IL
06/25 – 07/25
$731/nighttotal: $21930 (30 )
Livn West Loop Chicago 2 Br City View
2 3
apartment , Chicago
This downtown Chicago condo is an 8-minute walk from Skydeck Ledge and a 14-minute walk from State Street, with Clinton Station and Ogilvie Transportation Center within a 7-minute walk. This 650-square-foot apartment offers 2 bedrooms, 1 bathroom, a full kitchen with an ice dispenser, air conditioning, free Wi-Fi, and an in-unit washer and dryer, accommodating up to 4 guests.
Best Oak Park, IL vacation rentals with parking
Oak Park, IL
06/28 – 07/05
$363/nighttotal: $2541 (7 )
Chicago 3br Oasis Near Downtown & United Center
3 5
apartment , Chicago
This 3-bedroom apartment in Chicago is located 1.4 miles from the United Center and 3.2 miles from Union Station and Willis Tower. This spacious 10,760 sq ft residence accommodates up to 14 guests with amenities including a full kitchen, complimentary WiFi, and private parking.
9.5 253 reviews
Oak Park, IL
07/17 – 07/27
$259/nighttotal: $2590 (10 )
Pearly Gates | 3 Bed | Sleeps 5 | W/ 2-car Garage
3 1
apartment , Forest Park
This charming house is located in Forest Park, just a mile from Madison Street with its shops and restaurants, and a three-block walk to the CTA Blue Line "L" station, making it easy to get to downtown Chicago. This accommodation has consistently received excellent ratings for location, cleanliness, and overall user experience. The house has three bedrooms and one bathroom, offering ample space for relaxation and social gatherings. Guests can enjoy a fully equipped kitchen, a backyard, laundry facilities, and parking, along with flexible check-in and check-out options.
Oak Park, IL
06/28 – 07/03
$310/nighttotal: $1550 (5 )
Urban Oasis In The Heart Of Oak Park
2 2
apartment , Oak Park
This renovated 2-bedroom, 2-bathroom condo is located in Oak Park, offering a 1000 sq ft home with a fully equipped kitchen, spacious living area, and comfortable bedrooms, just a short commute to downtown Chicago. This unit accommodates up to 4 guests and includes amenities such as air conditioning, a balcony, and parking, with paid laundry facilities available in the building and proximity to downtown Oak Park's shops and dining.
10 11 reviews
Oak Park, IL
07/10 – 07/12
$2458/nighttotal: $4916 (2 )
Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar
6 14
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 Oak Park, IL
When is the best time to book a vacation rental in Oak Park, IL?
You'll want to book your vacation rental in advance, especially during peak season, which runs from May to October. If you're looking for a more affordable trip, consider visiting in the shoulder seasons, like April or November.
What are the best Airbnb and vacation rentals in Oak Park, IL?
What are the best restaurants with local dishes in Oak Park, IL?
For a classic Oak Park experience, try Hemingway's Bistro. They've got great American comfort food, and it's a local favorite. If you're looking for something a little more upscale, try The Purple Pig in Chicago, just a short drive from Oak Park.
What are the most popular Airbnbs in Oak Park, IL?
What are the best walking or cycling routes in Oak Park, IL?
The Oak Park River Forest Trail is a great option for a leisurely bike ride or walk. It's a paved trail that runs for about 10 miles along the Des Plaines River. For a shorter walk, try the Oak Park Conservatory's gardens.
What are the best vacation rentals with a pool in Oak Park, IL?
Are there pet-friendly attractions in Oak Park, IL?
The Oak Park River Forest Trail is great for walking your dog, and there are plenty of dog parks in the area. You can also check out the Oak Park Farmers Market, which is pet-friendly.
What are the best rentals for families and kids in Oak Park, IL?
What are the benefits of choosing a vacation rental in Oak Park, IL?
Vacation rentals offer more space and privacy than a hotel, and they're often more affordable, especially for families or groups. You'll also have access to a kitchen, which is great for saving money on meals.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?
What are the top sports attractions and facilities in Oak Park, IL?
Oak Park is home to the Oak Park-River Forest High School, which has a great athletic program. You can also find several parks and recreation centers with sports fields and courts.
Destinations nearby
Choose the Right Vacation Rentals with a Terrace in Oak Park, IL
Enjoy stunning views from your private terrace when you book one of these vacation rentals in Oak Park, IL.
Oak Park, IL
10/11 – 10/21
$306/nighttotal: $3060 (10 )
Chic Luxe Spa Retreat Light Filled King Bed Garage
1 2
apartment , Chicago
This apartment in Chicago offers a private garden and balcony, with complimentary parking and free WiFi, located in a neighborhood providing easy access to local attractions and transit. The 1100 square foot unit accommodates up to three guests and features a fully equipped kitchen, air conditioning, and a non-smoking environment.
9.0 1120 reviews
Oak Park, IL
06/28 – 07/03
$380/nighttotal: $1900 (5 )
The Hotel & Athletic Club At Midtown
1 2
resort , Chicago
The Hotel & Athletic Club at Midtown is located in Chicago's Midtown neighborhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The resort has received very good ratings for its location, cleanliness, and overall experience. This hotel offers spacious and modern rooms, each equipped with comfortable amenities. Guests can enjoy a wide range of activities and features, including a fitness center, swimming pool, spa, tennis courts, and a variety of dining options.
This 2-bedroom apartment is located in the Norwood Park/Edison Park neighborhood of Chicago, about 7.5 miles from Loyola University Chicago and 9.2 miles from Wrigley Field, offering a quiet and convenient location for exploring the city. The apartment is 910 square feet, comfortably accommodating up to 4 guests. The apartment has a fully equipped kitchen with a dishwasher and oven, as well as a washer and dryer for your convenience. Enjoy the outdoor space on the patio and garden, and stay connected with free Wi-Fi. The apartment also has a dedicated workstation, air conditioning, and outdoor play equipment for families.
9.4 7 reviews
Oak Park, IL
07/17 – 07/27
$549/nighttotal: $5490 (10 )
Sunny, Spacious, 3br 1ba Davlin Inn Chicago
3 1
apartment , Chicago
This three-bedroom Chicago apartment rental is situated in the Davlin Inn neighborhood, conveniently located 5-7 miles from attractions such as Wrigley Field, Lincoln Park Zoo, the United Center, and 360 Chicago Observation Deck. The 1300-square-foot dwelling boasts a spacious layout, accommodating up to nine guests and featuring a private patio with an outdoor fireplace, a fully equipped kitchen, free Wi-Fi, and access to on-site amenities including a playground and barbecue facilities.
Best Oak Park, IL vacation rentals with air conditioning
10 4 reviews
Oak Park, IL
06/25 – 07/25
$277/nighttotal: $8310 (30 )
3br Modern Apt • Gym • Workspace • Quiet Location
3 3
apartment , Dunning
This newly furnished 3-bedroom, 2-bathroom apartment is located in Dunning, a 15-minute drive from Chicago O'Hare International Airport and 25 minutes from Logan Square. This pet-friendly residence accommodates up to 9 guests and features a full kitchen with a dishwasher, central air conditioning, and a well-equipped gym with a Peloton bike, treadmill, and weights, plus a dedicated workspace with a dual-screen monitor.
9.8 553 reviews
Oak Park, IL
09/06 – 09/07
$896/nightfor 1 night
Coachhouse In Central Op 4 Blk To L
1 2
house , Oak Park
This charming house is located in the Frank Lloyd Wright Historic District, just a block from the farmers market and within walking distance of Hemingway and Frank Lloyd Wright attractions. It has excellent user, location, and cleanliness ratings. The house has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, laundry facilities, and amenities like TV/Xbox/FireTV, free parking, and WiFi.
10 49 reviews
Oak Park, IL
07/10 – 07/12
$2484/nighttotal: $4968 (2 )
Chicago Bootlegger House Sleeps 11-22 With 3 Parking Spots
6 14
apartment , Chicago
This single-family home sits in Chicago's East Lakeview neighborhood, just a short walk from Wrigley Field, Lincoln Park, and the lakefront, offering easy access to the city's attractions and vibrant atmosphere. The house has earned excellent user ratings, making it a popular choice for travelers. This spacious residence comfortably accommodates up to 20 guests, making it ideal for large families or groups. The home features a fully equipped kitchen, a Jacuzzi, a terrace with a garden, and parking for multiple vehicles, ensuring a comfortable and enjoyable stay.
9.7 127 reviews
Oak Park, IL
06/28 – 07/05
$195/nighttotal: $1365 (7 )
Entire Place 2 Bedrooms, Free Parking Train Access
2 5
apartment , Chicago
This two-bedroom Jefferson Park apartment is located steps away from the Jefferson Memorial Park and within walking distance of the Jefferson Park Transit Center, which provides easy access to O'Hare International Airport, Rosemont Entertainment District, and Downtown Chicago. The apartment has an excellent user, location, and cleanliness rating. The 880 square feet two-bedroom, one-bathroom apartment can accommodate up to six guests and features a fully equipped kitchen, a comfortable living area with a convertible sofa and a chaise, and a safe and secure building with surveillance cameras and a reserved parking spot. Coin-operated laundry facilities are also available in the building.