Holiday Rentals in Oak Park, IL

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Oak Park, IL holiday rentals
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Best Holiday rentals and Airbnb offers in Oak Park, IL

Explore Holiday Rentals for Families in Oak Park, IL

Travelling to Oak Park, IL with children? A quality family holiday rental or Airbnb makes everything easier with city attractions nearby.

Pilsen 8 Min-downtown Washerdryer 2300 Square Feet - Oak Park, IL
9.8 100 reviews
Oak Park, IL
10/07 – 12/07
£657/nighttotal: £1314 (2 )

Pilsen 8 Min-downtown Washerdryer 2300 Square Feet

4 14
apartment , Chicago
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.
Aurelien Spacious Apartments In The Heart Of Gold Coast - Oak Park, IL
9.7 537 reviews
Oak Park, IL
16/07 – 19/07
£1095/nighttotal: £3285 (3 )

Aurelien Spacious Apartments In The Heart Of Gold Coast

2 2
apartment , Chicago
This two-bedroom apartment is conveniently located in Chicago, just a short walk from Oak Street Beach and a mile from the city centre. It has received excellent ratings for location, cleanliness and user experience.
The apartment comes with a fully equipped kitchen, private bathroom and free Wi-Fi. You can also enjoy a range of amenities including a swimming pool, sauna, fitness centre and parking.
Like A Treehouse! - Oak Park, IL
10 367 reviews
Oak Park, IL
06/09 – 07/09
£593/nightfor 1 night

Like A Treehouse!

1 2
apartment , Forest Park
This charming coach house is situated in historic Forest Park, just 8 miles west of downtown Chicago, offering a convenient location close to the Blue Line train and I-290. The apartment has received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers.
The self-catering property offers one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, complimentary refreshments, and the option to borrow bicycles or kayaks.
Cute Chicago Attic Loft! Walk To Cta, Easy Travel - Oak Park, IL
9.9 49 reviews
Oak Park, IL
16/07 – 19/07
£186/nighttotal: £558 (3 )

Cute Chicago Attic Loft! Walk To Cta, Easy Travel

1 2
apartment , Chicago
This newly renovated attic flat is conveniently located in Chicago, near the junction of I-90 and I-94, offering easy access to public transport (a 5-minute walk to the train station and a 2-minute walk to the bus stop), and is relatively close to both O'Hare International Airport and Chicago's city centre.
The open-plan loft apartment sleeps four (two adults and two children), features a new kitchenette with fridge and microwave, a modern bathroom with a walk-in shower, and benefits from excellent transport links making it ideal for exploring the city.

Popular Holiday Rentals with Parking in Oak Park, IL

Park up and enjoy the city centre. These holiday rentals in Oak Park, IL come with a free car park on-site. Start comparing now.

Cozy Garden Suite Minutes From O'hare And Rosemont + Free Parking - Oak Park, IL
10 13 reviews
Oak Park, IL
06/09 – 07/09
£137/nightfor 1 night

Cozy Garden Suite Minutes From O'hare And Rosemont + Free Parking

1 2
apartment , Northlake
This Northlake flat is a 3.4-kilometre drive from the Donald E. Stephens Convention Centre and a 17.6-kilometre drive from the United Centre, with on-site parking.
This 269 square metre residence accommodates four guests and offers a full kitchen with a microwave, air conditioning, and Wi-Fi, as well as an in-unit washer and dryer.
Entire 3 Bedrm 2 Bath Coach House In Jeffersonpark - Oak Park, IL
9.8 50 reviews
Oak Park, IL
23/10 – 25/10
£256/nighttotal: £512 (2 )

Entire 3 Bedrm 2 Bath Coach House In Jeffersonpark

3 5
apartment , Chicago
This three-bedroom coach house is located in the quiet Jefferson Park neighbourhood, just 15 kilometres from O'Hare Airport and 30 kilometres from downtown Chicago. The property has excellent user, location and cleanliness ratings.
The apartment can accommodate up to six guests and features a fully equipped kitchen, a spacious living room, and a dining room. The property also includes a private entrance, secure parking for two cars, two decks, a washer and dryer, and modern amenities such as Wi-Fi and smart TVs.
Boho Dreamscape At Evy’s Place - Oak Park, IL
9.6 11 reviews
Oak Park, IL
23/10 – 25/10
£224/nighttotal: £448 (2 )

Boho Dreamscape At Evy’s Place

3 5
apartment , Berwyn
This Berwyn flat is situated 32 kilometres from downtown Chicago, providing convenient access to local amenities and just 35 minutes by car from O'Hare International Airport and 37 kilometres from Midway International Airport.
This three-bedroom flat accommodates up to seven guests, offering a boho-inspired design with a fully equipped kitchen, smart TVs in each bedroom, an arcade room, and in-building laundry facilities, with a highchair and pack-and-play available on request.
Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife - Oak Park, IL
10 2 reviews
Oak Park, IL
06/09 – 07/09
£598/nightfor 1 night

Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife

1 2
apartment , Chicago
This Level River North apartment, a stylish flat in Chicago's River North district, is minutes from the Magnificent Mile and across the river from the Loop.
The 56 square metre (602 square foot) studio suite sleeps four, offering a fully equipped kitchen, in-suite laundry, complimentary Wi-Fi, and access to a swimming pool, sauna, and parking; nearby attractions include the Chicago Theatre and Art Institute of Chicago.

Frequently asked questions about holiday rentals in Oak Park, IL

  • Which neighborhood in Oak Park, IL should you consider for a vacation rental?

    The best neighbourhood for a vacation rental in Oak Park would be the historic district, where you'll find many beautiful Victorian and Prairie-style homes. This area is close to the main shopping and dining areas and is within walking distance of many of the attractions.
  • What are the best Airbnb and holiday rentals in Oak Park, IL?

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

    Oak Park has plenty of family-friendly attractions, including the Oak Park Conservatory, with its beautiful gardens and exhibits, and the Oak Park River Forest Museum, which has interactive exhibits for children. The Scoville Park, with its playground and splash pad, is also a great place for families to spend time.
  • What are the most popular Airbnbs 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, from April to May or September to October, when the weather is still pleasant but the crowds are smaller. You'll also find better deals on rentals during these months.
  • What are the best holiday rentals with a pool in Oak Park, IL?

  • What events or festivals should visitors check out in and around Oak Park, IL?

    Oak Park hosts a variety of events throughout the year, including the Oak Park Festival of the Arts in June, which features art, music, and food vendors. The Taste of Oak Park in August is another popular event, showcasing local restaurants and food trucks. In the nearby city of Chicago, you'll find even more events, including the Chicago Air and Water Show in August and the Chicago Marathon in October.
  • What are the best rentals for families and kids in Oak Park, IL?

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

    You can enjoy many budget-friendly activities in Oak Park, such as exploring the many parks and green spaces, including the picturesque Scoville Park and the expansive Garfield Park Conservatory. You can also take a free walking tour of the historic district and visit the free exhibits at the Oak Park River Forest Museum.
  • What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?

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

    Oak Park has a diverse culinary scene, with many restaurants serving up local dishes. Try the classic American fare at the iconic FitzGerald's, a local favourite known for its live music and hearty meals. For a taste of Chicago-style pizza, head to the popular Lou Malnati's Pizzeria. If you are looking for something more casual, the Oak Park Ale House offers a wide selection of craft beers and pub food.
  • What are the best walking or cycling routes in Oak Park, IL?

    Oak Park is a great place to explore on foot or by bike. The Frank Lloyd Wright Historic District is a must-see for architecture enthusiasts, and the scenic trail along the Des Plaines River offers a peaceful escape from the city. For a longer ride, you can cycle along the 606, a former railway line that has been transformed into a popular bike path.
  • Are there pet-friendly attractions in Oak Park, IL?

    Oak Park is a very dog-friendly town, with many parks and businesses welcoming furry friends. The Scoville Park is a great place to let your dog run around, and many restaurants have outdoor seating where you can enjoy a meal with your pet. You can also take your dog for a walk along the Des Plaines River Trail.
  • What are the benefits of choosing a vacation rental in Oak Park, IL?

    Vacation rentals in Oak Park offer a more spacious and comfortable alternative to hotels. You'll have more privacy and flexibility, and you'll be able to enjoy the comforts of home while you're away. Many rentals also offer unique features, such as fireplaces, private patios, and hot tubs, which can enhance your stay.
  • What are the top sports attractions and facilities in Oak Park, IL?

    Oak Park has a variety of sports facilities, including the Oak Park Recreation Center, which offers a range of activities, including swimming, basketball, and fitness classes. The village also has several parks with sports fields, including the picturesque Scoville Park and the expansive Garfield Park. For those who enjoy golf, the nearby Oak Park Country Club offers a challenging 18-hole course.

Destinations nearby

Top Holiday Rentals with a Balcony in Oak Park, IL

Step onto your own terrace to take in stunning city skyline views. These holiday rentals in Oak Park, IL all include private outdoor space.

Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location - Oak Park, IL
8.1 30 reviews
Oak Park, IL
16/07 – 19/07
£382/nighttotal: £1146 (3 )

Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location

2 2
apartment , Chicago
Flexhome Ukrainian Village 2BR D2 is situated in Chicago's Ukrainian Village neighbourhood, 2.1km from the United Centre and 4.5km from Water Tower Place.
This two-bedroom apartment, offering 55 square metres of space, sleeps nine guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a balcony, and free Wi-Fi.
Stunning 3 Bedrooms 2 Bathrooms Getaway Chicago! - Oak Park, IL
10 1 review
Oak Park, IL
16/07 – 19/07
£784/nighttotal: £2352 (3 )

Stunning 3 Bedrooms 2 Bathrooms Getaway Chicago!

3 2
apartment , Chicago
This Chicago flat is situated in a residential district, approximately 8.5 kilometres from Wrigley Field and 10.3 kilometres from Lincoln Park Zoo.
This 242 square metre residence accommodates up to 15 guests, featuring three bedrooms, two bathrooms, air conditioning, a balcony, a garden, and a fully equipped kitchen with a dishwasher and microwave, alongside free WiFi.
Entire Apt In Heart Of Chicago - Oak Park, IL
9.8 8 reviews
Oak Park, IL
23/10 – 25/10
£280/nighttotal: £560 (2 )

Entire Apt In Heart Of Chicago

2 5
apartment , Chicago
This Chicago apartment, situated in Wrigleyville, is an 8-minute walk from Wrigley Field and within 3.5km of Lincoln Park Zoo and Fullerton Beach.
The one-bedroom, one-bathroom flat sleeps six guests and features a fully equipped kitchen, free Wi-Fi, a balcony, and a flat-screen TV; nearby attractions include Wrigley Field and Lincoln Park Zoo.
Stylish Cozy 3br Retreat With Free Parking Near Pilsen Art Center, Douglas Park And University Of Illinois Chicago - Oak Park, IL
10 1 review
Oak Park, IL
23/10 – 25/10
£380/nighttotal: £760 (2 )

Stylish Cozy 3br Retreat With Free Parking Near Pilsen Art Center, Douglas Park And University Of Illinois Chicago

3 5
apartment , Chicago
This stylish Chicago apartment, near Pilsen, is situated approximately 3.2km from the United Centre and within 7.2km of attractions including Union Station, the CIBC Theatre, and Grant Park.
The 139 square metre property features three bedrooms, two bathrooms, sleeps fifteen guests, and includes free parking, Wi-Fi, a fully equipped kitchen, and a terrace.

Best Oak Park, IL holiday rentals with air conditioning

The Evergreen House - Oak Park, IL
9.9 229 reviews
Oak Park, IL
28/06 – 05/07
£201/nighttotal: £1407 (7 )

The Evergreen House

1 5
apartment , Chicago
This first-floor flat is located in a quiet residential area of Chicago, just a short distance from the city centre and within easy reach of public transport. The apartment has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience.
The flat is ideal for families or groups of up to 5 people, with two bedrooms and one bathroom. It comes with a well-equipped kitchen, multiple TVs with access to Netflix, free street parking, a private backyard and a washer and dryer in the basement.
O'hare,2 Bedq K/washerd/parking. - Oak Park, IL
10 11 reviews
Oak Park, IL
25/06 – 25/07
£197/nighttotal: £5910 (30 )

O'hare,2 Bedq K/washerd/parking.

1 3
apartment , Franklin Park
This Franklin Park apartment, ideally located near public transport, restaurants, and parks, offers easy access to local amenities.
The two-bedroom, one-bathroom flat sleeps four guests comfortably, boasting a king and queen bed, plus sofas, a dedicated office, in-unit laundry, parking, and high-speed internet with Netflix.
Comfy Bed/free Parking&wifi /Nearhosp/ord/mdw/dt - Oak Park, IL
9.4 21 reviews
Oak Park, IL
20/07 – 27/07
£172/nighttotal: £1204 (7 )

Comfy Bed/free Parking&wifi /Nearhosp/ord/mdw/dt

1 1
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.
Giant 5br, Pool Table, 15 Min To Cubs & Mag Mile - Oak Park, IL
Oak Park, IL
10/07 – 12/07
£1060/nighttotal: £2120 (2 )

Giant 5br, Pool Table, 15 Min To Cubs & Mag Mile

5 14
house , Chicago
This five-bedroom detached house in Chicago is located 6.1 kilometres from Wrigley Field, offering a 15-minute journey to the Cubs and the Magnificent Mile.
This property spans 232 square metres and features five bedrooms, three bathrooms, air conditioning, and a fully equipped kitchen with a dishwasher and microwave, providing accommodation for up to 27 guests with free WiFi.
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