This two-bedroom apartment is situated in a peaceful part of Chicago, just a short distance from a church and with no immediate neighbours, offering a tranquil setting. It has consistently received excellent ratings for its cleanliness, location and overall experience. The property provides ample space for up to five guests and features a fully equipped kitchen with a dishwasher, as well as a spacious garden with a fire pit and a large vegetable patch. Guests can enjoy a variety of amenities, including central heating and air conditioning, a smart TV, and a private outdoor area perfect for relaxing or hosting small events.
9.8 16 reviews
Oak Park, IL
25/06 – 25/07
248 €/nighttotal: 7440 € (30 )
Oak Park Il · Charming Retro 2br Cottage/train/laundry/free Pkg
2 3
apartment , Oak Park
This Oak Park house, a short 2.3km from the Frank Lloyd Wright Historic District and 4.8km from Concordia University Chicago, offers convenient access to public transport and Chicago's attractions. The two-bedroom, one-bathroom property sleeps five, boasting a fully equipped kitchen with dishwasher, in-unit laundry, and a TV; nearby activities include visiting the United Center and Loyola University Medical Centre, both within 9.6km.
9.0 1120 reviews
Oak Park, IL
06/09 – 07/09
397 €/nightfor 1 night
The Hotel & Athletic Club At Midtown
1 2
resort , Chicago
The Hotel & Athletic Club at Midtown is conveniently located in Chicago's Midtown neighbourhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The hotel consistently receives high ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. The hotel offers a range of comfortable and modern rooms, each equipped with amenities such as air conditioning, flat-screen TVs, and private bathrooms. Guests have access to a wide array of facilities including indoor and outdoor swimming pools, a spa, a fitness centre, tennis courts, and a variety of fitness classes, making it a great choice for those seeking a wellness-focused getaway.
9.4 21 reviews
Oak Park, IL
16/07 – 19/07
256 €/nighttotal: 768 € (3 )
Comfy Bed/free Parking&wifi /Nearhosp/ord/mdw/dt
1 2
apartment , Berwyn
This one-bedroom flat is located just 5 kilometres from Oak Park, offering easy access to its charming downtown, Frank Lloyd Wright's homes, and the Hemingway District. The property has received excellent user ratings, highlighting its appeal to travellers. The flat is ideal for families or groups of up to 5 people, with a comfortable living area and a fully equipped kitchen. Amenities include air conditioning, parking, internet access, and a range of entertainment options, ensuring a comfortable and enjoyable stay.
9.8 451 reviews
Oak Park, IL
23/10 – 25/10
194 €/nighttotal: 388 € (2 )
Sunny Logan Square Artists' Home
1 5
apartment , Chicago
This Logan Square flat, a mile (1.6 km) from the Logan Square Blue Line station and a five-minute walk from the Metra, offers easy access to the 606 trail. The spacious three-bedroom second-floor property sleeps six, features a well-equipped kitchen with extra gadgets, a modern bathroom, shared laundry, a garden, parking, and fast internet with streaming services; nearby amenities include a grocery store 1.5 blocks away.
This apartment is situated in the trendy Pilsen neighbourhood, just 10 kilometres from the city centre and close to Chinatown, offering easy access to Chicago's attractions. The property boasts excellent user, location and cleanliness ratings. This spacious flat has four bedrooms and two bathrooms, comfortably accommodating up to 16 guests. The apartment is fully equipped with a kitchen, air conditioning, free street parking, and high-speed Wi-Fi, ensuring a comfortable and convenient stay.
9.8 553 reviews
Oak Park, IL
06/09 – 07/09
775 €/nightfor 1 night
Coachhouse In Central Op 4 Blk To L
1 2
house , Oak Park
This furnished apartment is located in Oak Park's Frank Lloyd Wright Historic District, just one kilometre from the farmers market and within walking distance of Hemingway and Frank Lloyd Wright attractions. The property has received excellent ratings for cleanliness, location and overall experience. The two-bedroom, one-bathroom property sleeps four guests and includes a fully equipped kitchen, in-unit laundry facilities, a private garage entrance and free WiFi. Guests can enjoy a range of entertainment options including a TV, Xbox and FireTV.
9.3 52 reviews
Oak Park, IL
25/06 – 25/07
201 €/nighttotal: 6030 € (30 )
Cozy Karlov (Loft) - 3 Beds 1 Bath
1 3
apartment , Chicago
This three-bedroom Chicago apartment is situated in the Avondale/Old Irving Park neighbourhood, offering convenient access to local restaurants and shops. The 3-bedroom loft-style flat sleeps up to five guests, features free on-site parking, and includes amenities such as air conditioning, Wi-Fi, and a fully equipped kitchen.
9.4 191 reviews
Oak Park, IL
06/09 – 07/09
349 €/nightfor 1 night
Entire Modern 2 Bedroom Apartment
2 2
apartment , Chicago
This modern two-bedroom flat is located in Chicago, just 10km from the United Center and 11km from Wrigley Field. It has received excellent ratings for cleanliness, location and user experience. The apartment is 9 square metres and can accommodate up to four guests. The flat comes with free Wi-Fi, air conditioning, a fully equipped kitchen and private parking, as well as access to a garden.
9.2 10 reviews
Oak Park, IL
25/06 – 25/07
243 €/nighttotal: 7290 € (30 )
Relaxing 2br Stay | Comfy Queen Bed + Fast Wifi
1 3
apartment , Chicago
This two-bedroom flat in Chicago is located near Lincoln Square and Albany Park, with the CTA Blue Line providing direct access to the city centre. This pet-friendly apartment accommodates up to five guests and features a fully equipped kitchen, high-speed Wi-Fi, and complimentary toiletries, with secure mail delivery advice also provided.
Oak Park, IL
23/10 – 25/10
540 €/nighttotal: 1080 € (2 )
Cozy Chic 4bd 2ba Oak Park Penthouse
4 5
apartment , Oak Park
This newly rehabbed contemporary flat is centrally located on Division Street in Oak Park, offering easy access to the town centre and situated less than 1.6 kilometres from the CTA/Metra station for swift journeys into Chicago. The spacious accommodation boasts four bedrooms and two bathrooms, comfortably housing up to eight guests with the convenience of in-unit climate control and free parking, while being a short distance from attractions like Millennium Park and the Art Institute of Chicago.
10 53 reviews
Oak Park, IL
06/09 – 07/09
446 €/nightfor 1 night
Serene 1-bedroom Suite In Oak Park (Free Parking!)
1 2
apartment , Oak Park
This Oak Park flat offers private, soundproofed accommodation located 12.8 kilometres west of central Chicago, with direct access to the Chicago Blue Line for travel to downtown and O'Hare International Airport. This newly renovated one-bedroom apartment accommodates two guests and features a kitchenette with a fridge and microwave, free off-street parking, and strong Wi-Fi, ideal for those seeking a convenient base for exploring the area.
Best family friendly Oak Park, IL holiday rentals
Among the 269 accommodations in Oak Park, IL, here are the 4 best family friendly rentals
This two-bedroom flat is situated in the Norwood Park/Edison Park neighbourhood of Chicago, a quiet area located 12 kilometres from Loyola University Chicago and 15 kilometres from Wrigley Field. The 85 square metre property can accommodate up to four guests and features a fully equipped kitchen, a patio, a garden, and outdoor play equipment, ideal for families with children.
9.7 66 reviews
Oak Park, IL
16/07 – 19/07
232 €/nighttotal: 696 € (3 )
Private Parking, Comfy Bed
1 2
apartment , Berwyn
This Berwyn apartment, ideally located for exploring the area, is an 8-minute walk from local restaurants and amenities, and within a 16-kilometre drive of Oak Park, Little Village, and Chicago's medical district. The one-bedroom flat offers a queen-size bed, sleeps four guests, includes free on-site parking, fast Wi-Fi, a 50-inch smart TV with streaming services, and a fully equipped kitchen; shared laundry facilities are also available.
10 20 reviews
Oak Park, IL
28/06 – 05/07
306 €/nighttotal: 2142 € (7 )
3 Bedroom Apartment, 15 Min Drive To Wrigley Field
1 5
apartment , Chicago
This three-bedroom flat is situated near Lincoln Square and Albany Park, offering direct CTA Blue Line access to central Chicago, with Wrigley Field a 15-minute drive away. This family-friendly apartment accommodates up to five guests and features a fully equipped kitchen, in-unit laundry, central air conditioning, and a comfortable living space with a 55-inch smart TV, all within easy reach of local dining and cultural attractions.
Oak Park, IL
28/06 – 05/07
314 €/nighttotal: 2198 € (7 )
Chicago 3br Oasis Near Downtown & United Center
3 5
apartment , Chicago
This Chicago three-bedroom flat is located 2.25 kilometres from the United Center and offers convenient access to downtown attractions such as Union Station and the Willis Tower, both 5.15 kilometres away. This family-friendly residence spans 1000 square metres, features three bedrooms, two bathrooms, and accommodates up to 14 guests with amenities including air conditioning, a fully equipped kitchen with a dishwasher, and free WiFi, plus a balcony and private parking.
Best Oak Park, IL holiday rentals with parking
8.6 9 reviews
Oak Park, IL
20/07 – 27/07
166 €/nighttotal: 1162 € (7 )
Luxurious, Cozy Beauty 10 Min From Downtown Chicago
1 1
apartment , Chicago
This one-bedroom flat is located in Chicago's Little Village neighbourhood, just 6 kilometres from Downtown Chicago and close to the United Center and McCormick Place. It has excellent user ratings and is perfect for those seeking a cultural experience in a lively area. The flat can comfortably accommodate up to 5 guests and is equipped with a fridge, microwave oven, WiFi and a desk. You'll also find an ironing board, kitchen utensils and a toaster, making it ideal for a comfortable stay.
10 1 review
Oak Park, IL
25/06 – 25/07
258 €/nighttotal: 7740 € (30 )
Charming Oak Park Retreat
2 3
apartment , Oak Park
This Oak Park flat, minutes from public transport links and the Frank Lloyd Wright Trust's Home and Studio, offers easy access to Chicago's city centre. The 118 square metre property boasts two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, free Wi-Fi, on-site parking, and a smart TV.
9.1 11 reviews
Oak Park, IL
20/07 – 27/07
213 €/nighttotal: 1491 € (7 )
Pearly Gates L 3 Bed L Sleeps 5 L W 2-car Garage
3 1
house , Forest Park
Pearly Gates, a three-bedroom holiday home in Forest Park, Illinois, is situated 12 kilometres from Midway International Airport and approximately 16 kilometres from Chicago landmarks such as the Willis Tower and Union Station. This 93-square-metre property sleeps up to thirteen guests, offering three bedrooms, one bathroom, a fully equipped kitchen with dishwasher and microwave, free Wi-Fi, parking for two cars, a garden, and air conditioning.
10 83 reviews
Oak Park, IL
06/09 – 07/09
1111 €/nightfor 1 night
Cozy Home In Brookfield
1 2
apartment , Brookfield
This Brookfield, Illinois home, situated in a peaceful neighbourhood, is an 8-minute walk (approximately 0.64 km) from Brookfield train station, offering easy access to downtown Chicago. This two-bedroom, one-bathroom property sleeps four guests and includes a kitchen with fridge, freezer, microwave, and dishwasher; air conditioning, internet access, and pets are permitted.
Frequently asked questions about holiday rentals in Oak Park, IL
What are the top family-friendly attractions in Oak Park, IL?
The Oak Park Conservatory is a beautiful and educational place for the whole family, with exotic plants and a lovely indoor garden. The nearby Scoville Park is also a great spot for kids, with playgrounds and a splash pad.
What are the best Airbnb and holiday rentals in Oak Park, IL?
When is the best time to book a vacation rental in Oak Park, IL?
The best time to book a vacation rental in Oak Park is during the shoulder seasons, in spring or autumn, when the weather is pleasant and the crowds are smaller. You'll get better deals on rentals and enjoy a more relaxed atmosphere.
What are the most popular Airbnbs in Oak Park, IL?
What are the best budget-friendly activities in Oak Park, IL?
Oak Park is full of free and budget-friendly activities. A walk or bike ride through the many parks, like the beautiful and historic Forest Home Cemetery, is a great way to enjoy the outdoors. The Oak Park Public Library is also a great resource for free events and activities.
What are the best holiday rentals with a pool in Oak Park, IL?
What are the best restaurants with local dishes in Oak Park, IL?
For a taste of local cuisine, try the legendary Maya Del Sol for authentic Mexican dishes, or the Oak Park Brewing Company for craft beers and pub food. You can't go wrong with either.
What are the best rentals for families and kids 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 walking or cycling, stretching for 16 km and following the Des Plaines River. The trail passes through parks and residential areas, offering a scenic and relaxing experience.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?
Are there pet-friendly attractions in Oak Park, IL?
Yes, many of Oak Park's parks and attractions are pet-friendly. The Oak Park Conservatory has a designated dog-walking area, and many restaurants have outdoor seating where you can enjoy a meal with your furry friend.
What are the benefits of choosing a vacation rental in Oak Park, IL?
Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.
What are the top sports attractions and facilities in Oak Park, IL?
Oak Park doesn't have any major sports teams or stadiums, but it does have a great community recreation center, the Oak Park Recreation Center, with a swimming pool, fitness center, and various sports courts.
Destinations nearby
Best Oak Park, IL holiday rentals with a balcony
Oak Park, IL
23/10 – 25/10
506 €/nighttotal: 1012 € (2 )
Modern Home Near Rosemont Allstate Arena O'hare Home
3 5
house , Des Plaines
This modern three-bedroom holiday home in Des Plaines is situated just 966 metres from Chicago O'Hare International Airport, offering convenient access to Chicago city centre attractions including Loyola University Chicago (19 kilometres) and Wrigley Field (21 kilometres). This spacious 102 square metre property comfortably accommodates up to 11 guests, boasting a fully equipped kitchen with a dishwasher, complimentary WiFi, air conditioning, a garden, and on-site yoga classes.
9.4 116 reviews
Oak Park, IL
28/06 – 05/07
884 €/nighttotal: 6188 € (7 )
Great Location! Spacious 6bd Home + Garage!
5 5
apartment , Chicago
This six-bedroom Chicago house, situated in a residential area near Wicker Park, Logan Square, and Bucktown, is a 10-minute walk from the Blue Line and a 32-kilometre drive from both Chicago airports. The 279-square-metre property boasts five bedrooms sleeping twelve guests, a fully equipped kitchen, a garden, parking, and is professionally cleaned, offering easy access to the North Branch of the Chicago River for summer kayaking.
10 1 review
Oak Park, IL
28/06 – 05/07
382 €/nighttotal: 2674 € (7 )
Secret Gallery On The Park - 2bd/1ba
2 5
apartment , Chicago
This three-bedroom Chicago apartment, ideal for families or groups of up to eight, is located in the Gallery District, a short walk from Oak Street Beach and the 'L' train, offering easy access to the John Hancock Center and Willis Tower. The two-level dwelling boasts two upgraded kitchens and bathrooms, a private patio, Roku access, complimentary Wi-Fi, and is within easy reach of shops and a grocery store.
9.0 1 review
Oak Park, IL
28/06 – 05/07
583 €/nighttotal: 4081 € (7 )
Dtown Penthouse 2bd Parking Gym, Pvt Patio #13
2 5
apartment , Chicago
This DTown Penthouse is located 1.8 kilometres from the city centre in a prime Chicago district, an 8-minute walk from DePaul University and close to Grant Park and the Art Institute of Chicago. This spacious two-bedroom flat, covering 103 square metres and accommodating up to seven guests, offers a private balcony with lake views, a fully equipped kitchen, air conditioning, free WiFi, and access to a fitness centre.
Best Oak Park, IL holiday rentals with air conditioning
9.8 72 reviews
Oak Park, IL
16/07 – 19/07
158 €/nighttotal: 474 € (3 )
Cute & Cozy Chicago Basement
1 2
apartment , Chicago
This recently remodelled one-bedroom basement flat in Chicago is located approximately 16km from O'Hare International Airport and a 16km drive from the Blue Line, providing easy access to the city centre. The 56-square-metre self-contained property offers a separate dining and living area (including a pull-out sofa bed), sleeping up to four guests, and boasts a fully equipped kitchen, private entrance, garden, parking, and excellent guest reviews.
9.1 621 reviews
Oak Park, IL
06/09 – 07/09
800 €/nightfor 1 night
The Double Play - Modern 2br Apts Right Next To Wrigley Field & Transit! - Perfect For Cubs Fans
2 2
apartment , Chicago
This two-bedroom apartment is located in the Lakeview neighbourhood, just a 3.7km walk from Lincoln Park Zoo and a short distance from Wrigley Field, a famous baseball stadium known for its lively atmosphere. The apartment has received very good ratings for cleanliness and user experience, and an excellent rating for its location. The apartment has one bathroom and includes a terrace, garden, and parking. It is equipped with a kitchen including a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning and free Wi-Fi.
8.0 1 review
Oak Park, IL
25/06 – 25/07
275 €/nighttotal: 8250 € (30 )
Mins To Dt & Frank Lloyd Wright
1 3
apartment , Oak Park
This one-bedroom flat in Oak Park offers a prime location, just 400 metres from the Frank Lloyd Wright Home and Studio and a 10-minute walk from Downtown Oak Park, with immediate access to popular eateries. This pet-friendly apartment accommodates up to four guests, featuring a kitchen with a fridge and microwave, air conditioning, a garden, and parking, with flexible check-in/out options available.
9.8 191 reviews
Oak Park, IL
28/06 – 05/07
367 €/nighttotal: 2569 € (7 )
Picture-perfect Oak Park Home- 18 Mins To Downtown
1 5
apartment , Oak Park
This Oak Park bungalow is located on a peaceful street just a short drive from downtown Chicago and O'Hare Airport, making it a convenient base for exploring the city and beyond. The property has received excellent ratings for location, cleanliness, and overall guest experience. The spacious home features four bedrooms, sleeping up to nine guests, and a large kitchen with modern appliances. Guests can enjoy the convenience of a dishwasher, a washing machine and dryer, and a fully equipped kitchen, as well as the relaxing outdoor space with a gazebo.