Best Holiday rentals and Airbnb offers in Oak Park, IL
10 3 reviews
Oak Park, IL
28/06 – 03/07
SG$358/nighttotal: SG$1790 (5 )
Cozy Extended Stay: King Bed/fully Equipped/train
1 2
apartment , Oak Park
This Oak Park flat is ideally situated for exploring local landmarks, with the Frank Lloyd Wright Historic District a 11-minute walk and the Ernest Hemingway Museum and House a 14-minute walk away. This one-bedroom flat accommodates two guests and offers on-site parking, a fully equipped kitchen, and in-unit laundry, with excellent public transport links to Chicago's attractions.
9.4 71 reviews
Oak Park, IL
17/07 – 27/07
SG$341/nighttotal: SG$3410 (10 )
Mins To Dt & Frank Lloyd Wright
1 1
apartment , Oak Park
This Oak Park studio apartment is ideally located near Petersen's Ice Cream and Broken Tart, less than 0.6km from Frank Lloyd Wright's Home and Studio, and a 1km walk from Oak Park's town centre. The self-contained unit sleeps three guests, offering a kitchen with fridge, freezer, and microwave, plus air conditioning, Wi-Fi, parking, a garden, and is within easy reach of Giordano's and other restaurants.
10 157 reviews
Oak Park, IL
06/09 – 07/09
SG$1072/nightfor 1 night
Stylish Coachhouse In Lovely Oak Park!
1 2
house , Oak Park
This one-bedroom coach house is situated in Oak Park, a short walk from the L train and a local brewery, and a short drive from central Chicago. The property features a full kitchen, a private patio, and a fenced-in parking spot, accommodating up to four guests.
10 1 review
Oak Park, IL
25/06 – 25/07
SG$159/nighttotal: SG$4770 (30 )
Perfect Location By Everything!
2 3
apartment , Dunning
This Dunning apartment, centrally located within the town, offers easy access to Dunning's attractions, although precise distances are not specified. The three-bedroom, one-bathroom flat sleeps seven guests and includes a kitchen, air conditioning, and internet access; further interior details are unavailable.
9.5 110 reviews
Oak Park, IL
06/09 – 07/09
SG$649/nightfor 1 night
Pulaski Point Properties
1 2
apartment , Chicago
Apartment rental with an excellent rating of 95% based on 110 reviews. Your accommodation will be located in Chicago. Facilities and services include 24-hour entry, a kitchen and air conditioning.
9.8 68 reviews
Oak Park, IL
11/10 – 21/10
SG$196/nighttotal: SG$1960 (10 )
Cozy Garden Unit In Historic Mayfair
1 2
apartment , Chicago
This Chicago Mayfair garden flat is conveniently located approximately 1.6 kilometres from the Interstate 90/94 expressway and within 1.6 kilometres of the Montrose Blue Line station, offering easy access to public transport and O'Hare International Airport. The ground-floor, one-bedroom apartment sleeps two guests and includes a fully equipped kitchen, a modern bathroom, and unique access to fresh eggs from the on-site chickens; nearby attractions include the North Branch Trail, a 22.5-kilometre cycling path.
9.8 67 reviews
Oak Park, IL
11/10 – 21/10
SG$559/nighttotal: SG$5590 (10 )
Oak Park Home W/ Grill - 5 Mi To Garfield Park!
3 2
house , Oak Park
This charming Oak Park house is situated just 14 kilometres from the United Center, 16 kilometres from Lincoln Park Zoo, and 18 kilometres from Union Station, offering easy access to Chicago's attractions. It is located in a quiet neighbourhood within the historic village of Oak Park, known for its beautiful architecture and vibrant arts scene. The house has received excellent ratings for cleanliness, location, and user experience. The property has three bedrooms and one bathroom, spanning 167 square metres and comfortably accommodating up to six guests. Enjoy amenities such as a fully equipped kitchen, free Wi-Fi, a private fire pit, and a peaceful setting, perfect for a relaxing getaway.
9.9 158 reviews
Oak Park, IL
10/07 – 12/07
SG$2410/nighttotal: SG$4820 (2 )
Chicago Bootlegger House Sleeps 10-20
6 14
bungalow , Chicago
This six-bedroom house is located in a lively neighbourhood, just a short walk from Lake Michigan, Lincoln Park Zoo, Wrigley Field, and the Red Line train. It has received excellent ratings for location, cleanliness, and overall user experience. This spacious property can comfortably accommodate up to sixteen guests and features a fully equipped kitchen, a private rooftop deck, and a range of entertainment options including a foosball table, vintage slot machine, board games, and a working fireplace.
9.9 31 reviews
Oak Park, IL
28/06 – 05/07
SG$280/nighttotal: SG$1960 (7 )
Modern 2 Bd Near The 606 Trail | W&d | Luxtel
1 5
apartment , Chicago
This centrally located Chicago apartment, ideal for families, offers easy street parking with a provided permit and is conveniently situated within the city, though precise proximity to specific landmarks is not detailed. The 2-bedroom, 1-bathroom flat sleeps up to six guests, boasting a newly renovated interior with modern furnishings, a fully equipped kitchen including Samsung appliances, and amenities such as a 55" flat-screen TV with Netflix, complimentary snacks, and a private ground-floor entrance.
9.8 8 reviews
Oak Park, IL
17/07 – 27/07
SG$175/nighttotal: SG$1750 (10 )
Nice Place On The West Side Of Chicago
1 1
apartment , Chicago
This one-bedroom flat in Chicago's tranquil district offers a peaceful escape with convenient access to local attractions. This property accommodates up to four guests and provides essential amenities including air conditioning, Wi-Fi, a kitchen, and parking, with pets welcome.
9.4 65 reviews
Oak Park, IL
28/06 – 03/07
SG$411/nighttotal: SG$2055 (5 )
Spacious Oak Park Home, 11 Mi To Downtown Chicago!
3 2
house , Oak Park
This comfortable house is situated in Oak Park, just 18 kilometres from downtown Chicago and 14 kilometres from the United Center, offering easy access to the city's attractions. The property has received excellent ratings for its location, cleanliness, and overall experience. This spacious three-bedroom home, spanning 223 square metres, comfortably accommodates up to six guests. The house boasts a well-equipped kitchen, laundry facilities, a garden, and parking, ensuring a comfortable and enjoyable stay.
9.8 36 reviews
Oak Park, IL
11/10 – 21/10
SG$290/nighttotal: SG$2900 (10 )
A Quiet Stay While You Are Away
2 2
apartment , Oak Park
This apartment is in the Frank Lloyd Wright historic district, a short walk from Unity Temple and the town centre. It has excellent user ratings and is popular with families. The home has two bedrooms and can comfortably sleep four people. Guests can enjoy a garden, a terrace, a fully-equipped kitchen and parking.
Best family friendly Oak Park, IL holiday rentals
Among the 269 accommodations in Oak Park, IL, here are the 4 best family friendly rentals
9.9 170 reviews
Oak Park, IL
11/10 – 21/10
SG$376/nighttotal: SG$3760 (10 )
Historic Coach House In Evanston One Block To Beach And Close To Town And Nu!
1 2
apartment , Evanston
This historic manor house is situated in Evanston's Lakeshore Historic District, just 0.8 kilometres from Lake Michigan's beaches and a short walk from downtown Evanston and Northwestern University. The property has received excellent ratings for its location, cleanliness, and overall user experience. The house has one bedroom and one bathroom spread over 84 square metres, comfortably accommodating up to three guests. The property offers a range of amenities, including a fully equipped kitchen, a private garden, a spa, parking, and complimentary bicycles and beach passes for exploring the area and enjoying the lake.
10 1 review
Oak Park, IL
17/07 – 27/07
SG$400/nighttotal: SG$4000 (10 )
Studio Near Wrigley Sleeps 4 Games + Fireplace
1 1
studio , Chicago
This Irving Park apartment is situated approximately 3.2 kilometres from Wrigley Field and offers straightforward access to Chicago's attractions, including Lincoln Park Zoo and the Field Museum. This 74 square metre studio apartment accommodates up to four guests and features a fully equipped kitchen, a Smart TV, complimentary Wi-Fi, and on-site laundry facilities, with pets welcome for an additional fee.
10 104 reviews
Oak Park, IL
17/07 – 27/07
SG$607/nighttotal: SG$6070 (10 )
Modern 3-bed Stay W/ Patio, Firepit, & Garage Parking Spot
3 1
apartment , Chicago
This three-bedroom flat is situated in Logan Square, a lively neighbourhood in Chicago, a 15-minute walk from the CTA Blue Line train, 15 minutes by car to the city centre, and 20 minutes by car to O'Hare International Airport. The property has excellent user, location, and cleanliness ratings. The apartment is 93 square metres and can accommodate up to six guests. It has a modern and stylish interior with a spacious backyard, a fully equipped kitchen, a private entrance, high-speed internet, a smart TV, a parking space, and a gas fire pit.
8.5 9 reviews
Oak Park, IL
28/06 – 05/07
SG$399/nighttotal: SG$2793 (7 )
The Karlov. Gorgeous ,Spacious 2bd/ 1ba W/ Parking
2 5
apartment , Chicago
The Karlov apartment in Chicago is conveniently located a short drive (approximately 6.3 km) from the United Centre, and within reasonable driving distance of Lincoln Park Zoo, the Museum of Contemporary Art Chicago, and 360 Chicago Observation Deck. This 102 square metre two-bedroom, one-bathroom flat sleeps up to nine guests and offers free parking, Wi-Fi, a fully equipped kitchen, and amenities including a patio, seating area, and fireplace.
Best Oak Park, IL holiday rentals with parking
Oak Park, IL
28/06 – 05/07
SG$481/nighttotal: SG$3367 (7 )
Modern 3br South Loop Living Family Unit Near Adler Planetarium & Mccormick Convention Center
3 5
apartment , Chicago
This three-bedroom Chicago apartment, near the Museum Campus, is 2.3km from the Field Museum and under 3.2km from Grant Park and the Art Institute of Chicago. The 88-square-metre property boasts two bathrooms, sleeps eight guests, includes free Wi-Fi, private parking (optional), a fitness centre, and a patio with city views; a fully equipped kitchen and family-friendly features are also available.
9.6 55 reviews
Oak Park, IL
28/06 – 03/07
SG$234/nighttotal: SG$1170 (5 )
Quiet West Loop 1br W/backyard Near Cta, Greenline
1 2
apartment , Chicago
This newly renovated basement flat in Chicago offers a peaceful retreat on a quiet street, just 10 minutes by public transport from the West Loop, with the Green Line station a mere 100 metres away. This one-bedroom flat accommodates up to three guests and features a full kitchen, in-unit laundry, and a shared patio with a barbecue, providing all the necessary amenities for a comfortable stay.
10 1 review
Oak Park, IL
25/06 – 25/07
SG$384/nighttotal: SG$11520 (30 )
Charming Oak Park Retreat
2 3
apartment , River Forest
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.
10 11 reviews
Oak Park, IL
10/07 – 12/07
SG$3159/nighttotal: SG$6318 (2 )
Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar
6 14
apartment , Chicago
This six-bedroom home is situated in Jefferson Park, a quiet neighbourhood in Chicago, just 10 kilometres from Navy Pier and Michigan Avenue, and within easy reach of the airport and downtown. The property has received excellent reviews from previous guests. The apartment offers 297 square metres of space, comfortably accommodating up to 16 guests. It features a fully equipped kitchen, a games room, a spa, a garden, a terrace, parking, and a Super Mario-themed bunk room for kids.
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
9.7 124 reviews
Oak Park, IL
28/06 – 03/07
SG$423/nighttotal: SG$2115 (5 )
Family Apartment W/ Deck + Yard Near Northwestern
1 2
apartment , Evanston
This apartment is located in Evanston, Illinois, just 8.2 kilometres from Wrigley Field and 17.7 kilometres from Lincoln Park Zoo, making it a convenient base for exploring the city. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. The property has two bedrooms and can accommodate up to six guests in its 111 square metres of space. Amenities include a fully equipped kitchen, a private deck and yard, air conditioning, free Wi-Fi, and parking, ensuring a comfortable and enjoyable stay.
10 3 reviews
Oak Park, IL
17/07 – 27/07
SG$710/nighttotal: SG$7100 (10 )
Artsy West Town Flat Near Downtown
2 1
apartment , Chicago
This West Town flat is centrally located in Chicago, offering easy access to attractions such as the Art Institute of Chicago and Michigan Avenue. The 93-square-metre (1000 sq ft) property boasts two bedrooms, two bathrooms, a private deck, and in-unit laundry facilities, comfortably accommodating six guests and featuring a fully equipped kitchen and smart TV.
9.4 3 reviews
Oak Park, IL
11/10 – 21/10
SG$504/nighttotal: SG$5040 (10 )
Irving Park/avondale Updated Vintage Top Unit In 2-flat
2 2
apartment , Chicago
This Irving Park flat is situated 2.4 kilometres from Milwaukee Avenue, offering easy access to the Addison and Irving Park Blue Line stations and is within 9.6 kilometres of Wrigley Field and the Walt Disney House. The two-bedroom, one-bathroom apartment sleeps six, features a terrace, fully equipped kitchen including a dishwasher, free Wi-Fi, and on-site barbecue facilities.
Oak Park, IL
28/06 – 03/07
SG$266/nighttotal: SG$1330 (5 )
Trendy Unit-15mins To Downtown!
1 2
apartment , Chicago
This stylish one-bedroom flat in Bronzeville offers excellent access to McCormick Place (1.5 km), Wintrust Arena, and the Illinois Institute of Technology, with the Field Museum and Art Institute of Chicago a short journey away. This apartment accommodates up to four guests and includes internet, air conditioning, a balcony, and parking, making it ideal for exploring Chicago's cultural attractions and shopping districts.
Best Oak Park, IL holiday rentals with air conditioning
9.3 51 reviews
Oak Park, IL
25/06 – 25/07
SG$299/nighttotal: SG$8970 (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.
Oak Park, IL
17/07 – 27/07
SG$267/nighttotal: SG$2670 (10 )
The Urban Oasis
1 1
apartment , Chicago (IL)
Book this vacation rental. You will be in Chicago (IL). Services and facilities: free parking, a kitchen and a dish washer. Take advantage of the air conditioning in this apartment in Chicago (IL).
9.9 31 reviews
Oak Park, IL
28/06 – 05/07
SG$324/nighttotal: SG$2268 (7 )
Modern & Comfy Gem Near Transit
1 5
apartment , Chicago
This apartment is situated in East Garfield Park, a short distance from the Garfield Park Conservatory and public transport links. This 3-bedroom flat accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, high-speed Wi-Fi, and Smart TVs, with easy access to local amenities and Chicago landmarks.
9.8 175 reviews
Oak Park, IL
17/07 – 27/07
SG$505/nighttotal: SG$5050 (10 )
Cozy, Comfortable And Convenient Apartment. Close To Everything!
2 1
apartment , Oak Park
This charming studio apartment is situated in Oak Park's Arts District, just a short walk from the Frank Lloyd Wright Home and Studio, and a mere 400 feet from the CTA Blue Line, making it easy to explore both Oak Park and downtown Chicago. The studio consistently receives excellent ratings for its location, cleanliness, and overall experience. This comfortable apartment offers two bedrooms and one bathroom across 86 square metres. Guests can enjoy a fully equipped kitchen, a private garden, a spa, and parking, as well as keyless access and a patio with a grill for warm weather enjoyment.
