Best Holiday rentals and Airbnb offers in Oak Park, IL
8.0 1 review
Oak Park, IL
20/07 – 27/07
SG$402/nighttotal: SG$2814 (7 )
Explore Chicago! / King Bd Near Train / Near Shops
1 1
apartment , Oak Park
This Oak Park flat is situated a short walk from the Frank Lloyd Wright Historic District (704 metres) and the Ernest Hemingway Museum and House (893 metres), with two metro stations also within a 13-minute walk for convenient travel. This one-bedroom flat accommodates two guests and includes a kitchenette with a fridge and microwave, air conditioning, on-site parking, and in-unit laundry facilities, offering easy access to Chicago's major attractions.
8.9 215 reviews
Oak Park, IL
28/06 – 05/07
SG$470/nighttotal: SG$3290 (7 )
Modern 2br Loft With Amazing City Skyline View And Optional Parking For 8 Guests Near Mccormick Place And Soldier Field
3 5
apartment , Chicago
This modern apartment is located in Chicago's McCormick Place district, just a short distance from the Field Museum of Natural History and the Art Institute of Chicago. The property has received excellent ratings for location, cleanliness, and overall user experience. The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, a fitness centre, a terrace, and on-site parking, making it perfect for families or groups of friends exploring the city.
9.5 145 reviews
Oak Park, IL
20/07 – 27/07
SG$235/nighttotal: SG$1645 (7 )
1br/1ba City Comfort
1 1
apartment , Chicago
This Chicago one-bedroom apartment, ideal for couples or solo travellers, is situated in an upper-level unit accessible only via stairs, its precise neighbourhood unspecified but likely in a denser area of the city. The self-contained flat offers a fully equipped kitchen, including a fridge and dishwasher, sleeps two guests, features reliable Wi-Fi, a smart TV, and requires a government-issued ID for security verification.
9.1 621 reviews
Oak Park, IL
06/09 – 07/09
SG$1189/nightfor 1 night
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2br Apts
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.
9.5 232 reviews
Oak Park, IL
23/10 – 25/10
SG$476/nighttotal: SG$952 (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.
9.5 55 reviews
Oak Park, IL
16/07 – 19/07
SG$340/nighttotal: SG$1020 (3 )
1 Bedroom Apartment In Lovely Victorian House
1 2
apartment , Oak Park
This apartment is conveniently located in Oak Park, just 2km from the train station, offering a quick 20-minute commute to Chicago, and is situated in a peaceful, family-friendly neighbourhood. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment is ideal for couples, with one bathroom and a well-equipped kitchen. You can enjoy amenities such as Wi-Fi, air conditioning, and a fridge, freezer, and microwave.
Oak Park, IL
20/07 – 27/07
SG$440/nighttotal: SG$3080 (7 )
Oak Park Gem Next To Green Line In Unit Laundry
2 1
apartment , Oak Park
This Oak Park flat offers convenient access, located approximately 24 kilometres from Chicago and a short distance from local attractions such as Frank Lloyd Wright's Home and Studio. This spacious 93 square metre apartment features two bedrooms and two bathrooms, accommodating up to four guests, and includes in-unit laundry, a fully equipped kitchen, air conditioning, a balcony, and access to a fitness centre and rooftop deck.
8.9 17 reviews
Oak Park, IL
25/06 – 25/07
SG$328/nighttotal: SG$9840 (30 )
Chic City Escape
1 3
apartment , Berwyn
This three-bedroom Berwyn apartment, sleeping five, boasts an excellent location offering easy access to Berwyn's attractions; precise distances to specific landmarks require further detail. The property features a fully equipped kitchen including fridge, freezer, and microwave, air conditioning, parking, and is centrally located for convenient exploration of the town.
Oak Park, IL
10/07 – 12/07
SG$1826/nighttotal: SG$3652 (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.
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.
Oak Park, IL
28/06 – 05/07
SG$251/nighttotal: SG$1757 (7 )
Great Area Logan Square Apt Games Pets - Sleeps 5
1 5
apartment , Chicago
This private top-floor flat is situated in Chicago's Avondale/Logan Square district, approximately 12.8 to 16 kilometres from downtown landmarks such as the Merchandise Mart and Cloud Gate. This 58-square-metre accommodation allows pets, offers high-speed internet, air conditioning, parking, and features a PacMan arcade machine and wall-sized Connect 4 for entertainment, with a capacity for five guests.
9.8 72 reviews
Oak Park, IL
16/07 – 19/07
SG$235/nighttotal: SG$705 (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.
Best family friendly Oak Park, IL holiday rentals
Among the 269 accommodations in Oak Park, IL, here are the 4 best family friendly rentals
Oak Park, IL
28/06 – 05/07
SG$555/nighttotal: SG$3885 (7 )
Spacious 3br Condo With Skyline Views Near Mccormick Place & Soldier Field
3 5
apartment , Chicago
This three-bedroom Chicago apartment, situated in the Near South Side, is ideally located near McCormick Place convention centre and a short walk from a subway station, offering easy access to the Museum Campus and the city centre. The 88-square-metre (947 square feet) property boasts a spacious layout, comfortably sleeping up to eight guests, and includes amenities such as a fully equipped kitchen, on-site gym, and EV charging stations; nearby attractions include Soldier Field and the Art Institute of Chicago.
9.0 2 reviews
Oak Park, IL
23/10 – 25/10
SG$502/nighttotal: SG$1004 (2 )
Modern Oak Park Getaway 3br 2ba With Yard, 20 Mins To Chicago Loop, Near Train
3 5
apartment , Oak Park
This luxurious three-bedroom apartment is situated in downtown Oak Park, offering convenient access to Chicago's attractions such as the Art Institute of Chicago, the Chicago Theatre, the Willis Tower, and the Merchandise Mart, though precise distances aren't specified. The 139 square metre (1496 square foot) property features two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, in-unit laundry, and a private garden with parking.
9.9 30 reviews
Oak Park, IL
28/06 – 05/07
SG$466/nighttotal: SG$3262 (7 )
Paradise In The Park
1 5
apartment , Berwyn
This Berwyn flat offers excellent access to Chicago's central business district (32 kilometres), Midway Airport (16 kilometres), hospitals (16 kilometres), and Brookfield Zoo (16 kilometres), with direct garden access to a park featuring new playgrounds, soccer fields, and a walking trail. This family-friendly accommodation for up to nine guests boasts four bedrooms, two bathrooms, air conditioning, Wi-Fi, and a well-equipped kitchen, with ample parking and a garden making it ideal for stays in Berwyn.
9.4 191 reviews
Oak Park, IL
23/10 – 25/10
SG$341/nighttotal: SG$682 (2 )
Entire Modern 2 Bedroom Apartment
2 5
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.
Best Oak Park, IL holiday rentals with parking
Oak Park, IL
25/06 – 25/07
SG$256/nighttotal: SG$7680 (30 )
2br Near Ohare Oak Park Coffee Nook
2 3
apartment , Elmwood Park
This Elmwood Park apartment, conveniently located 8km from Chicago O'Hare International Airport and within 16-18km of attractions such as Wrigley Field, Lincoln Park Zoo, and the United Center, offers easy access to Chicago's highlights. The 500 square metre property boasts two bedrooms, one bathroom, and sleeps up to ten guests, featuring a fully equipped kitchen, garden, complimentary Wi-Fi, and in-unit laundry facilities.
This Brighton Park flat, situated on a main road with a bus stop directly outside, offers easy access to Chicago's attractions. Sleeping up to six guests, this ground-floor apartment boasts a fully equipped kitchen including a large fridge, oven, microwave and Keurig machine, plus a 50" Smart TV, free Wi-Fi, keyless entry, and an in-unit safety deposit box; optional garage parking is available at an extra cost.
Oak Park, IL
28/06 – 05/07
SG$466/nighttotal: SG$3262 (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.
10 170 reviews
Oak Park, IL
23/10 – 25/10
SG$516/nighttotal: SG$1032 (2 )
Gather In Spacious 3 Bedroom 2 Bath Retreat
3 5
apartment , Forest Park
Mohr Cottage, a recently renovated house in a quiet Forest Park residential neighbourhood, is located a short walk from local restaurants and shops, and a short drive from downtown Chicago. This three-bedroom, two-bathroom property sleeps up to ten guests, offering a fully equipped kitchen with modern appliances, a garden, and parking, plus amenities such as high chairs and travel cots for families.
Frequently asked questions about holiday rentals in Oak Park, IL
Which neighborhood in Oak Park, IL should you consider for a vacation rental?
The area around the Oak Park Avenue and Lake Street intersection is a great choice, lots of shops, restaurants and cafes, and it's close to the train station for easy access to Chicago.
What are the best Airbnb and vacation rentals in Oak Park, IL?
What are the top family-friendly attractions in Oak Park, IL?
The Oak Park Conservatory is a great place for kids to learn about plants and nature, and the park has a fantastic playground. The Scoville Park is also a great option, it has a splash pad and a playground, perfect for a family day out.
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 is during the shoulder seasons, April-May and September-October, as prices are typically lower and the weather is still pleasant.
What are the best vacation rentals with a pool in Oak Park, IL?
What events or festivals should visitors check out in and around Oak Park, IL?
The Oak Park Festival of the Arts is a popular event held in August, with art displays, live music and food stalls. The Chicago Blues Festival, held in June, is a short train ride away and is a great way to experience the city's vibrant music scene.
What are the best rentals for families and kids in Oak Park, IL?
What are the best budget-friendly activities in Oak Park, IL?
The Oak Park River Forest Museum is free to enter and offers a fascinating glimpse into the history of the area. The Oak Park Public Library is another great option, with free events and activities throughout the year.
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?
The Purple Pig is a popular spot for locally sourced ingredients and creative dishes. Maya Del Sol is a great option for authentic Mexican cuisine.
What are the best walking or cycling routes in Oak Park, IL?
The 1.5km long Oak Park River Forest Trail is a great option for a walk or cycle, running along the Des Plaines River. The area around the Frank Lloyd Wright Home and Studio is also a nice area for a stroll, with many beautiful historic buildings to admire.
Are there pet-friendly attractions in Oak Park, IL?
The Oak Park Conservatory welcomes well-behaved dogs on leash, so you can enjoy the beauty of the gardens with your furry friend. The Scoville Park also has a designated off-leash dog area.
What are the benefits of choosing a vacation rental in Oak Park, IL?
Vacation rentals offer more space and privacy than a hotel, and often come with a kitchen, which can be useful for families or those on a budget. They can also be a good option for longer stays.
What are the top sports attractions and facilities in Oak Park, IL?
The Oak Park Recreation Department offers a range of sports facilities, including tennis courts, basketball courts, and a swimming pool. The nearby Forest Park, just a short drive away, also has a large park with sports fields and a golf course.
Destinations nearby
Best Oak Park, IL holiday rentals with a balcony
10 1 review
Oak Park, IL
16/07 – 19/07
SG$1351/nighttotal: SG$4053 (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.
10 3 reviews
Oak Park, IL
16/07 – 19/07
SG$2043/nighttotal: SG$6129 (3 )
Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12
3 2
apartment , Chicago
This West Town apartment, situated in Chicago, is conveniently located within a 5-8km radius of attractions such as Fulton Market, the United Centre, Grant Park, Michigan Avenue, and Lake Michigan. Sleeping up to 12 guests, this three-bedroom, three-bathroom dwelling boasts a king suite with fireplace and steam shower, a queen suite with private roof deck access, a fully equipped kitchen with balcony, a private garage, and a stunning roof deck with Willis Tower views.
9.6 685 reviews
Oak Park, IL
06/09 – 07/09
SG$1664/nightfor 1 night
4 Bedroom Home In Best Location Parking Fireplace Back Yard Pets Welcome
4 2
house , Chicago
This four-bedroom holiday home is located in Chicago's Old Town district, just a short walk from Oak Street Beach and Lincoln Park Zoo, offering easy access to the city's attractions and restaurants. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. The house is spacious and comfortable, accommodating larger groups with ease. Guests can enjoy a range of amenities, including a fully equipped kitchen, a patio, a garden, a spa, a fitness centre, and a tennis court.
9.9 32 reviews
Oak Park, IL
16/07 – 19/07
SG$2888/nighttotal: SG$8664 (3 )
Avenir West Loop Penthouses With Iconic City Views
3 2
apartment , Chicago
Cloud9 - 730, a presidential penthouse apartment in Chicago, is situated approximately 2.6 to 3 km from Union Station, Water Tower Place, the Museum of Contemporary Art, and the Shops at Northbridge. This pet-friendly dwelling boasts a terrace, garden, free parking, and Wi-Fi, offering comfortable accommodation with air conditioning, a seating area, and wardrobe in each unit.
Best Oak Park, IL holiday rentals with air conditioning
10 20 reviews
Oak Park, IL
28/06 – 05/07
SG$455/nighttotal: SG$3185 (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
10/07 – 12/07
SG$2618/nighttotal: SG$5236 (2 )
4br Modern Urban Escape Walk To Zoo Lakefront & Red Line
2 14
house , Chicago
This 4-bedroom modern urban escape is located in Chicago, offering city views and convenient access, approximately 2.7 kilometres from North Avenue Beach and 3.2 kilometres from Water Tower Chicago and 360 Chicago. This detached house spans 112 square metres and accommodates up to 16 guests, featuring air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, as well as an on-site water park and patio.
9.5 21 reviews
Oak Park, IL
25/06 – 25/07
SG$224/nighttotal: SG$6720 (30 )
Lory’s Cozy Place! Safe,convinient,15 Min To Loop!
3 3
apartment , Chicago
This apartment is situated in the Central Park neighbourhood of Chicago, just 1.6 kilometres from the Chicago Loop and a 15-minute commute by train. The apartment has received excellent reviews for its cleanliness, location, and user experience. This three-bedroom flat comfortably accommodates five guests and features a fully equipped kitchen with a fridge, freezer, and microwave oven. The apartment also boasts air conditioning, a garden, parking, and high-speed Wi-Fi.
Oak Park, IL
06/09 – 07/09
SG$425/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.
