This Elmwood Park apartment is located just 1.4 km from the Frank Lloyd Wright Historic District and 2.4 km from the Ernest Hemingway Museum and House, offering easy access to these popular attractions. The apartment consistently receives excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The flat has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private garden, and a terrace, providing everything you need for a relaxing and enjoyable stay.
Oak Park, IL
16/07 – 19/07
A$360/nighttotal: A$1080 (3 )
The Urban Oasis
1 2
apartment , Chicago (IL)
Accommodation. You will stay in Chicago (IL). Services and facilities: a kitchen, a fridge and free parking.
9.7 60 reviews
Oak Park, IL
23/10 – 25/10
A$636/nighttotal: A$1272 (2 )
Sweet Home Oak Park
1 5
apartment , Oak Park
This Oak Park apartment rental is conveniently located near Oak Park train station, offering easy access to Chicago city centre. The three-bedroom, two-bathroom property sleeps six, includes in-unit laundry, free parking, and a private porch and yard, all within walking distance of local pubs and coffee shops.
10 14 reviews
Oak Park, IL
28/06 – 05/07
A$337/nighttotal: A$2359 (7 )
Charming 3br Getaway 10min From Midway Airport
3 5
apartment , Cicero
This Cicero flat offers easy access, being a mere 1600 metres from Midway Airport and a short walk to shops and public transport, with downtown Chicago just 3200 metres away. This 3-bedroom residence accommodates up to 5 guests and features a fully equipped kitchen, air conditioning, a garden, and in-unit laundry, plus shared use of a backyard and garage parking.
9.9 133 reviews
Oak Park, IL
06/09 – 07/09
A$1215/nightfor 1 night
O'malley Oasis!
1 2
house , Oak Park
This charming coach house studio is located in a central Oak Park neighbourhood, just a short walk from the bustling downtown area and within a few blocks of public transport links. Guests have consistently praised its excellent location, cleanliness, and overall experience. The studio has one bedroom and one bathroom, comfortably accommodating two guests. It features a well-equipped kitchen, a relaxing living area with a big-screen TV, a private porch, and a dedicated parking space.
9.8 97 reviews
Oak Park, IL
10/07 – 12/07
A$5405/nighttotal: A$10810 (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.
9.8 50 reviews
Oak Park, IL
23/10 – 25/10
A$487/nighttotal: A$974 (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.
10 134 reviews
Oak Park, IL
06/09 – 07/09
A$1360/nightfor 1 night
Cheerful Oak Park Apartment
1 2
apartment , Oak Park
This Oak Park flat is situated above a piano restoration shop, within a 0.8 km radius of cafes, restaurants, and grocery stores, and close to the Frank Lloyd Wright Home and Studio and the Oak Park Conservatory. The one-bedroom apartment, sleeping two guests, offers a spacious open-plan living area with a king-size bed, private deck, fully equipped kitchen, and access to a fitness centre; enjoy complimentary coffee, tea, and snacks.
9.8 48 reviews
Oak Park, IL
25/06 – 25/07
A$584/nighttotal: A$17520 (30 )
Luxury Oasis With Parking Only 10min From Chicago
1 3
apartment , Forest Park
This Forest Park apartment is conveniently located near Madison Street, a short drive (approximately 16km) from downtown Chicago and within walking distance of public transport, including the Chicago Green/Blue Line and Metra. Sleeping 8-12 guests, this two-bedroom, one-bathroom dwelling boasts a full kitchen, private garden, free on-site parking, and a modern interior; a 24/7 host is available.
9.9 178 reviews
Oak Park, IL
20/07 – 27/07
A$324/nighttotal: A$2268 (7 )
Custom Apartment In The Heart Of Avondale
1 1
apartment , Chicago
This two-bedroom Chicago apartment is situated a short 0.32-kilometre walk from the Belmont Blue Line station, providing easy access to the city centre, Wrigley Field, and O'Hare International Airport. The second-floor flat offers a fully equipped kitchen, Netflix, cable TV, and sleeps up to six guests in two bedrooms and a pull-out sofa bed, complemented by on-site amenities including a garden, fitness centre, and parking.
9.6 22 reviews
Oak Park, IL
10/07 – 12/07
A$5519/nighttotal: A$11038 (2 )
:: The Wolcott :: Modern Elegance At Its Finest
6 14
apartment , Chicago
This exquisite 6000 sq ft (557 sq m) single-family home is situated in Chicago's Wicker Park neighbourhood, offering easy access to the city's attractions. The property boasts a spacious layout with four ensuite bedrooms and additional sleeping space for up to 16 guests, featuring a private 800 sq ft (74 sq m) garden, rooftop decks with Chicago skyline views, a jacuzzi, a fitness centre, and parking; other amenities include a wine cellar, pool table, and keyless entry.
Oak Park, IL
06/09 – 07/09
A$471/nightfor 1 night
Coach Casa Penthouse - Minutes From Downtown
1 2
apartment , Chicago
The Coach Casa Penthouse is located in Chicago, 4.2 kilometres from the United Center and 6.9 kilometres from the Willis Tower. This 60 square metre flat offers one bedroom, one bathroom, and can accommodate up to seven guests, featuring air conditioning, free private parking, and complimentary high-speed WiFi.
Best family friendly Oak Park, IL holiday rentals
Among the 269 accommodations in Oak Park, IL, here are the 4 best family friendly rentals
10 18 reviews
Oak Park, IL
20/07 – 27/07
A$615/nighttotal: A$4305 (7 )
Downtown Chicago - Spa Bath, Patio, 3 Blocks To L
1 1
apartment , Chicago
This apartment is located in downtown Chicago, just a short walk from Navy Pier and Michigan Avenue, making it easy to explore the city’s attractions and vibrant nightlife. It has received excellent reviews from previous guests. The one-bedroom apartment spans 88 square metres and comfortably accommodates up to four guests. It boasts a fully equipped kitchen, a spa bathroom with a jetted tub and a rain shower, and a terrace where you can relax and enjoy the city views.
9.6 163 reviews
Oak Park, IL
23/10 – 25/10
A$545/nighttotal: A$1090 (2 )
Urban Chic 3beds W/2bath + Free Parking & W/d
3 5
apartment , Oak Park
This Oak Park house, boasting three bedrooms and one bathroom, offers convenient access to Chicago's city centre via public transport. Sleeping six guests, the property features a fully equipped kitchen, garden, air conditioning, and excellent guest reviews, providing a comfortable and peaceful stay near Oak Park's shops and restaurants.
9.9 49 reviews
Oak Park, IL
16/07 – 19/07
A$354/nighttotal: A$1062 (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.
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.
Best Oak Park, IL holiday rentals with parking
9.9 379 reviews
Oak Park, IL
23/10 – 25/10
A$778/nighttotal: A$1556 (2 )
Family-friendly, Stylish Chicago Apartment In Logan Square
3 5
apartment , Chicago
This charming Chicago flat is situated in Logan Square, a popular neighbourhood known for its trendy restaurants, bars, and art galleries, and is within easy reach of the 606 Bloomingdale Trail and the Logan Square Farmers Market. The apartment has received excellent ratings for its location, cleanliness, and overall experience. This three-bedroom home offers 111 square metres of space and can comfortably accommodate up to seven guests. It comes equipped with a well-stocked kitchen, a private garden, laundry facilities, and a range of amenities for families, including a baby-friendly pack-and-play and toys.
Oak Park, IL
25/06 – 25/07
A$708/nighttotal: A$21240 (30 )
139 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 3
house , Cicero
Accommodation for up to 6 guests. Your accommodation will be based in Cicero. Services and facilities: a washing machine, a kitchen and a freeze.
9.2 12 reviews
Oak Park, IL
10/07 – 12/07
A$2736/nighttotal: A$5472 (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.
10 164 reviews
Oak Park, IL
23/10 – 25/10
A$778/nighttotal: A$1556 (2 )
100 Yr. Old Chicago Brick Craftsman With Yard, Near Beach And Loyola!
3 5
apartment , Chicago
This charming three-bedroom flat is situated in a historic Chicago neighbourhood, just 3 kilometres from Lake Michigan and a 2.4 kilometre walk to Wrigleyville. The property has received excellent ratings for location, cleanliness, and overall user experience. The 139 square metre apartment comfortably accommodates up to eight guests and features a spacious layout with a sunroom and a dining room that can seat up to 10 people. Guests can enjoy a fully equipped kitchen, a charming backyard, parking facilities, and family-friendly amenities such as a baby gate and toddler dishes.
Frequently asked questions about holiday rentals in Oak Park, IL
What are the top family-friendly attractions in Oak Park, IL?
Oak Park has plenty for families! The Oak Park Conservatory is a great place to visit, with its beautiful gardens and educational exhibits. The Oak Park River Forest Museum is also a popular choice, with interactive exhibits that are fun for all ages. And don't forget the Oak Park Farmers Market, which is held every Saturday from May to October.
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 in the spring or autumn. The weather is mild, and the crowds are smaller. You'll be able to enjoy all that Oak Park has to offer without the summer heat or the winter chill.
What are the most popular Airbnbs in Oak Park, IL?
What are the best restaurants with local dishes in Oak Park, IL?
Oak Park has a fantastic food scene. For a taste of local cuisine, try The Purple Pig for its creative dishes and The Map Room for its classic American fare. And don't forget to grab a slice of pizza at Pizzeria Bebu, a local favourite.
What are the best holiday rentals with a pool in Oak Park, IL?
What are the best walking or cycling routes in Oak Park, IL?
Oak Park has a great network of walking and cycling trails. The Forest Trails are a popular choice for a scenic stroll or bike ride. You can also explore the Oak Park River Forest Trail, which winds its way through the village and offers beautiful views of the Des Plaines River.
What are the best rentals for families and kids in Oak Park, IL?
Are there pet-friendly attractions in Oak Park, IL?
Oak Park is a very dog-friendly town! Many of the parks and restaurants welcome furry friends. The Oak Park Conservatory has a designated dog-walking area, and the Forest Trails are perfect for a leisurely stroll with your pup.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?
What are the benefits of choosing a vacation rental in Oak Park, IL?
Choosing a vacation rental in Oak Park can be a great option for families or groups who want more space and privacy than a hotel room. You'll also have access to a kitchen, so you can save money by cooking your own meals. And many vacation rentals are located in quiet neighbourhoods, offering a more peaceful experience than a hotel in the heart of the city.
Destinations nearby
Best Oak Park, IL holiday rentals with a balcony
9.7 239 reviews
Oak Park, IL
23/10 – 25/10
A$763/nighttotal: A$1526 (2 )
Wrigley Oasis! Steps From The Field! - 3bd 1ba
3 5
apartment , Chicago
This apartment is located in the Lakeview neighbourhood of Chicago, just 0.5km from Wrigley Field and a short drive from Montrose Beach, making it ideal for exploring the city's vibrant atmosphere and attractions. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This three-bedroom flat with one bathroom is 111 square metres in size and can accommodate up to six guests. It comes with a fully equipped kitchen, a terrace, a garden, a spa, and parking, as well as air conditioning and free Wi-Fi, making it perfect for families or groups travelling to 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.
9.4 50 reviews
Oak Park, IL
23/10 – 25/10
A$873/nighttotal: A$1746 (2 )
3br Modern Condo Near Wrigley/dwtn +Free Parking
3 5
apartment , Chicago
This fully furnished apartment is located in Lincoln Park, a lively Chicago neighbourhood, just 8 kilometres from Wrigley Field, 12 kilometres from downtown Chicago, and 40 kilometres from O'Hare airport. The property has received excellent user ratings and is ideal for families and groups. The apartment spans 111 square metres and comfortably accommodates up to 7 guests in its 4 bedrooms. It features a fully equipped kitchen, a private study, a washer and dryer, free parking, and a garden.
8.0 1 review
Oak Park, IL
06/09 – 07/09
A$1109/nightfor 1 night
Stay Chic In Chicago: River North Suites W/ Luxe Amenities & Prime Location!
1 2
apartment , Chicago
This Level River North apartment, situated in Chicago's River North district, is minutes from the Magnificent Mile and the Loop, offering easy access to the Chicago River and its cultural attractions. The 48-square-metre studio flat features a sofa bed, sleeping space for four guests, a fully equipped kitchen (fridge, microwave, dishwasher), and access to a swimming pool, sauna, and parking; nearby water activities include motor boating.
Best Oak Park, IL holiday rentals with air conditioning
9.2 10 reviews
Oak Park, IL
25/06 – 25/07
A$399/nighttotal: A$11970 (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.
10 20 reviews
Oak Park, IL
28/06 – 05/07
A$503/nighttotal: A$3521 (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.
9.5 232 reviews
Oak Park, IL
23/10 – 25/10
A$527/nighttotal: A$1054 (2 )
Free Parking & Wifi In Bucktown/logan Square Apt, Close To Everything!
2 5
apartment , Chicago
This Chicago apartment, ideally located three blocks (approximately 0.24 km) from a train station providing easy access to the city centre, is also within walking distance or a short drive of numerous restaurants, shops, and theatres. The 93 square metre (1000 sq ft) property boasts two bedrooms, one bathroom, and sleeps five, featuring a fully equipped kitchen, in-unit laundry, a jacuzzi, and optional free parking; tennis courts are also available.
9.9 128 reviews
Oak Park, IL
28/06 – 05/07
A$723/nighttotal: A$5061 (7 )
Oak Park Victorian By Flw Studio
1 5
apartment , Oak Park
This Oak Park studio apartment is situated in the Frank Lloyd Wright district, a short walk from the Frank Lloyd Wright Home and Studio and Ernest Hemingway's home. The newly renovated Victorian property offers four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, high-speed internet, smart TVs, and free private parking for up to three vehicles.