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.

Luxury Designer Penthouse Loft | Sleeps 20 - Oak Park, IL
9.2 12 reviews
Oak Park, IL
10/07 – 12/07
£1436/nighttotal: Â£2872 (2 )

Luxury Designer Penthouse Loft | Sleeps 20

4 14
apartment , Chicago
This penthouse apartment is situated in Wicker Park, a trendy neighbourhood in Chicago, just a short distance from Michigan Avenue, Navy Pier, and the Field Museum of Natural History. It has received excellent reviews from previous guests.
The apartment is spacious, spanning 418 square metres and comfortably accommodating up to 20 guests. It offers a fully equipped kitchen, a smart TV, a record player, and a large sectional sofa, ensuring a comfortable and enjoyable stay.
Kng + Qn 2bdrm/1 Free Parking By O’hare/allstate - Oak Park, IL
9.7 158 reviews
Oak Park, IL
25/06 – 25/07
£118/nighttotal: Â£3540 (30 )

Kng + Qn 2bdrm/1 Free Parking By O’hare/allstate

1 3
apartment , Melrose Park
This two-bedroom flat in Melrose Park is conveniently located just 16km from O'Hare International Airport and a short distance from the vibrant village of Oak Park. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat is spacious and comfortable, comfortably accommodating up to four guests. It comes fully equipped with a modern kitchen, including a fridge, freezer, and microwave oven, along with air conditioning, free internet, and private parking.
Appartement-d'exception-salle De Bain Privée-vue S - Oak Park, IL
9.9 88 reviews
Oak Park, IL
17/07 – 27/07
£287/nighttotal: Â£2870 (10 )

Appartement-d'exception-salle De Bain Privée-vue S

3 1
apartment , Oak Park
This three-bedroom flat is situated in the heart of Oak Park, just a short walk from Ernest Hemingway's birthplace and a number of Frank Lloyd Wright studios, offering a unique opportunity to explore the area's rich architectural heritage. The property has excellent ratings for location, cleanliness and user experience.
The flat has a spacious layout and can accommodate up to six guests, making it ideal for families or groups of friends. It comes with a well-equipped kitchen, two garages, high-speed internet, a garden and air conditioning, offering everything you need for a comfortable stay.
Classic Oak Park Home, 11 Mi To Downtown Chicago! - Oak Park, IL
9.2 95 reviews
Oak Park, IL
11/10 – 21/10
£420/nighttotal: Â£4200 (10 )

Classic Oak Park Home, 11 Mi To Downtown Chicago!

4 2
house , Oak Park
This four-bedroom house is situated in Oak Park, just 17 kilometres from downtown Chicago and 16 kilometres from Union Station, offering a peaceful setting within easy reach of the city's attractions. The property has received very good user ratings and excellent location and cleanliness ratings.
The 165 square metre house comfortably accommodates up to eight guests. It features a fully equipped kitchen with a dishwasher and oven, air conditioning, free Wi-Fi, a washing machine, a garden, a spa, and parking.

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 12 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.
Urban Oasis In The Heart Of Oak Park - Oak Park, IL
Oak Park, IL
28/06 – 03/07
£232/nighttotal: Â£1160 (5 )

Urban Oasis In The Heart Of Oak Park

2 2
apartment , Oak Park
This beautifully renovated two-bedroom, two-bathroom flat is located in Oak Park, offering convenient access to downtown amenities and transit, with easy connections to central Chicago.
This 93 square metre residence accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace or balcony, and on-site paid laundry facilities.
Spacious 3br Rogers Park Town House Budget-friendly - Oak Park, IL
8.0 3 reviews
Oak Park, IL
28/06 – 05/07
£327/nighttotal: Â£2289 (7 )

Spacious 3br Rogers Park Town House Budget-friendly

3 5
apartment , Chicago
This West Ridge townhouse in Chicago offers convenient access to attractions such as the Chicago Theatre and Art Institute of Chicago, though precise distances aren't specified.
The three-bedroom property, sleeping up to five guests, includes a queen bed, two twin beds, air conditioning, Wi-Fi, and a bathroom with a bathtub; nearby amenities include Michigan Avenue and Navy Pier.
The Avondale Lower Level - Oak Park, IL
9.7 435 reviews
Oak Park, IL
11/10 – 21/10
£149/nighttotal: Â£1490 (10 )

The Avondale Lower Level

2 2
apartment , Chicago
This garden flat is located in the Irving Park neighbourhood, just 5km from Wrigley Field and 11km from downtown Chicago. It benefits from excellent user, location and cleanliness ratings, making it a great choice for travellers.
The property is a 93 square metre, two-bedroom flat with a guest capacity of four. It offers a private entrance, free parking, a well-equipped kitchen, comfortable bedding, a laundry facility, and a garden.

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.

Sage Modern Apartments Near Union Park In West Loop - Oak Park, IL
8.9 41 reviews
Oak Park, IL
28/06 – 05/07
£505/nighttotal: Â£3535 (7 )

Sage Modern Apartments Near Union Park In West Loop

2 5
apartment , Chicago
This two-bedroom apartment is situated in the Union Park neighbourhood, just 1.6 km from Union Station and within walking distance of popular attractions like Willis Tower, United Center, and the Art Institute of Chicago. The surrounding area offers a mix of residential streets and local shops and restaurants.
This comfortable flat offers 100 square metres of space and can accommodate up to 5 guests. You will enjoy a range of amenities including a fully equipped kitchen, a private terrace, a fitness centre, and air conditioning.
Garage Parking - Vintage Charm - And A Fabulous Location! Easily Enjoy The Best Of Chicago! - Oak Park, IL
9.6 306 reviews
Oak Park, IL
11/10 – 21/10
£350/nighttotal: Â£3500 (10 )

Garage Parking - Vintage Charm - And A Fabulous Location! Easily Enjoy The Best Of Chicago!

2 2
apartment , Chicago
This two-bedroom Chicago apartment is situated in a neighbourhood a 1.6km walk from Chicago's best bars and restaurants.
The property offers a fully equipped kitchen, including a fridge, microwave, and dishwasher, accommodates four guests, and includes a private garage parking space, plus access to a shared garden.
1 #31 - 4 Bedroom Condo - Mccormick Place, Wintrust Arena, Chinatown - Oak Park, IL
9.7 1018 reviews
Oak Park, IL
28/06 – 05/07
£386/nighttotal: Â£2702 (7 )

1 #31 - 4 Bedroom Condo - Mccormick Place, Wintrust Arena, Chinatown

5 5
apartment , Chicago
This newly renovated dual-suite apartment is located in Chicago's Chinatown, just a short walk from public transport and a 5-kilometre drive from downtown and other attractions like Millennium Park. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment has two separate living spaces, each with its own kitchen, dining room, and living room, making it ideal for larger groups. Each suite is fully equipped with modern appliances, including a fridge, freezer, microwave, dishwasher, and air conditioning, along with a terrace, garden, and spa.
Stunning 2 Floor Apt With Rooftop - View Of Loop! - Oak Park, IL
9.4 353 reviews
Oak Park, IL
17/07 – 27/07
£737/nighttotal: Â£7370 (10 )

Stunning 2 Floor Apt With Rooftop - View Of Loop!

3 1
apartment , Chicago
This Noble Square/West Town duplex apartment is ideally situated within walking distance of many Chicago attractions.
This spacious 149-square-metre (1600 sq ft) three-bedroom, two-and-a-half-bathroom property boasts a rooftop deck with city skyline views, a private backyard, and accommodates up to twelve guests, featuring a fully equipped kitchen, in-unit laundry, and on-site management.

Best Oak Park, IL holiday rentals with air conditioning

Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location! - Oak Park, IL
9.8 152 reviews
Oak Park, IL
10/07 – 12/07
£2836/nighttotal: Â£5672 (2 )

Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!

6 14
apartment , Chicago
Loft606 Chicago is situated in a former factory district, just 2.4km from the Magnificent Mile and 3.2km from Millennium Park, offering a unique blend of industrial charm and modern luxury. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This spacious apartment spans 493 square metres and features a 26-foot timber beamed ceiling, skylights, and a massive gourmet kitchen. Guests can enjoy a full-size bar, a fireplace, a sound system, a garden patio, a rooftop deck, a spa, a fitness centre, a tennis court, and parking.
3 Stylish 2brs Steps From Magnificent Mile - Oak Park, IL
Oak Park, IL
10/07 – 12/07
£3392/nighttotal: Â£6784 (2 )

3 Stylish 2brs Steps From Magnificent Mile

1 14
apartment , Chicago
This luxurious six-bedroom, six-bathroom apartment in Chicago's Gold Coast offers stunning city skyline views and is situated close to Lake Michigan, with easy access to ice skating rinks and the city's upscale shopping and dining.
The 24th, 25th or 26th-floor flat boasts a spacious layout sleeping up to 15 guests, featuring a fully equipped kitchen, a fitness centre, swimming pool, and extensive building amenities including a social club, gaming centre, and meditation lounges.
Grove Flat - Oak Park, IL
10 13 reviews
Oak Park, IL
06/09 – 07/09
£724/nightfor 1 night

Grove Flat

1 2
apartment , Oak Park
This two-bedroom flat in Oak Park's Hemingway District offers excellent access to Chicagoland, being just a 4-minute walk from the Green Line.
This pet-friendly rental provides space for four guests with a private covered porch, shared garden access, a dedicated parking spot, and modern kitchen and bathroom facilities, all within an excellent user-rated property.
Studio Apartment In Oak Park - Oak Park, IL
9.9 108 reviews
Oak Park, IL
06/09 – 07/09
£686/nightfor 1 night

Studio Apartment In Oak Park

1 2
studio , Oak Park
This Oak Park studio apartment is ideally situated in the historic district, mere steps from Ernest Hemingway's birthplace and a short walk (less than 0.5 km) from Frank Lloyd Wright's Home and Studio.
The self-contained unit, sleeping up to two guests, features a queen-sized bed, a compact kitchenette with fridge, freezer and microwave, a newly updated bathroom, and a private garden; nearby attractions include numerous cafes, shops, restaurants, a cinema and convenient access to CTA/Metra public transport.
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