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.
9.1 16 reviews
Oak Park, IL
25/06 – 25/07
$356/nighttotal: $10680 (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.
9.5 4 reviews
Oak Park, IL
10/07 – 12/07
$4329/nighttotal: $8658 (2 )
Six-bedrooms In Wrigleyville
1 14
apartment , Chicago
This Wrigleyville apartment rental sleeps up to 16 guests and is situated near Wrigley Field in Chicago's North Side, offering easy access to Wrigleyville's restaurants and bars. The six-bedroom, two-bathroom property features two combined apartments with spacious living areas, a shared back deck, parking permits available upon request, and includes all necessary amenities such as a fully equipped kitchen and air conditioning.
10 13 reviews
Oak Park, IL
25/06 – 25/07
$372/nighttotal: $11160 (30 )
“The Sunflower Suite” 420 Friendly - Free Parking
2 3
apartment , Chicago
This Northwest Chicago flat is situated in a culturally diverse neighbourhood, conveniently located steps from the 77 CTA bus route offering easy access to the city's attractions. The two-bedroom apartment, sleeping up to six guests, boasts a fully equipped kitchen, shared garden, fitness centre, parking, and 420-friendly designated areas; laundry facilities are available for stays exceeding five days.
9.8 51 reviews
Oak Park, IL
28/06 – 03/07
$226/nighttotal: $1130 (5 )
Serene One Bedroom One Bath Apartment Near Chicago
1 2
apartment , Forest Park
This Forest Park flat is situated near the Interstate 290, a short walk from public transport links, and 13 kilometres from Chicago city centre. The one-bedroom apartment, sleeping two, boasts a kitchen with fridge, freezer and microwave, air conditioning, a garden, parking, and proximity to six tennis courts in a nearby park; guests enjoy excellent cleanliness and location ratings.
9.7 23 reviews
Oak Park, IL
25/06 – 25/07
$411/nighttotal: $12330 (30 )
Modern 2br Near O’hare • Parking • Private Yard
1 3
apartment , Franklin Park
This Franklin Park flat is conveniently located near Franklin Park’s train station, offering easy access to O'Hare International Airport (approximately 16 km away) and Interstate 294. The newly refurbished two-bedroom apartment, sleeping four, boasts a fully equipped kitchen, in-unit laundry, fast Wi-Fi, a dedicated workspace, and a private fenced deck; free on-site parking is also provided.
9.7 42 reviews
Oak Park, IL
28/06 – 03/07
$206/nighttotal: $1030 (5 )
New Jade Haven In Berwyn/riverside
1 2
apartment , Berwyn
Jade Haven, a one-bedroom apartment in Berwyn, offers pet-friendly accommodation with convenient amenities including free parking and internet access. This self-catering flat sleeps four guests and features a fully equipped kitchen, a restful bedroom, and a luxurious bathroom; precise location within Berwyn is unspecified.
9.4 42 reviews
Oak Park, IL
17/07 – 27/07
$405/nighttotal: $4050 (10 )
Explore Chicago! | King Bd Near Train | Near Shops
1 1
apartment , Oak Park
This Oak Park flat, a short walk (0.8km) from the Green Line CTA train station and a few blocks from Historic Downtown Oak Park, offers easy access to Chicago and Frank Lloyd Wright's architecture (a 1.6km drive). The first-floor apartment, sleeping two guests in a king-size bed, features a fully equipped kitchen, 50" smart TV, fast Wi-Fi, radiant floor heating (68-71°F), and is ideal for those with mobility concerns due to its only three steps to access.
9.6 676 reviews
Oak Park, IL
06/09 – 07/09
$1809/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.
10 11 reviews
Oak Park, IL
10/07 – 12/07
$3435/nighttotal: $6870 (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.
10 6 reviews
Oak Park, IL
10/07 – 12/07
$1798/nighttotal: $3596 (2 )
Giant 5br W/ Pool Table, 15 Min To Cubs & Mag Mile
1 14
apartment , Chicago
This substantial five-bedroom residence in Chicago's Irving Park district offers convenient access to major attractions, situated a 15-25 minute Uber journey from landmarks such as Wrigley Field, the city centre, The Bean sculpture, Soldier Field, the United Center, and the Riverwalk. This early 1900s Craftsman Foursquare property accommodates up to 14 guests with its five bedrooms featuring hotel-quality bedding, three bathrooms, a fully equipped kitchen with a large peninsula, and a dedicated games room complete with a pool table and a 75-inch smart television, all supported by high-speed Wi-Fi.
9.9 43 reviews
Oak Park, IL
11/10 – 21/10
$262/nighttotal: $2620 (10 )
Large Unit In Prime Logan Square
1 2
apartment , Chicago
This garden flat is located in Chicago's Logan Square district, a short walk to numerous bars, restaurants, and the 606 trail. This one-bedroom flat accommodates up to three guests and features a kitchenette, air conditioning, and free street parking, with smart lock entry for convenience.
Best family friendly Oak Park, IL vacation rentals
Among the 269 accommodations in Oak Park, IL, here are the 4 best family friendly rentals
9.0 17 reviews
Oak Park, IL
11/10 – 21/10
$467/nighttotal: $4670 (10 )
Rustic Apt /Near Hosp/ 25mins To Ord/mdw/dt/free Parking & Wifi
1 2
apartment , Berwyn
This one-bedroom flat in Berwyn is ideally located just a two-minute walk from restaurants and local entertainment, and a five-minute walk from the BNSF Metra station. It has received excellent ratings from previous guests. The apartment can accommodate up to four guests and includes a fully equipped kitchen, a comfortable queen-size bed, and a 50-inch TV with streaming services. Guests can enjoy free parking and Wi-Fi, as well as access to a spa and other amenities.
10 4 reviews
Oak Park, IL
10/07 – 12/07
$2372/nighttotal: $4744 (2 )
Bootlegger House Sleeps 10-20 Free Tv & Parking
6 14
apartment , Chicago
This Chicago apartment, ideal for large groups, is situated in a peaceful neighbourhood near Lincoln Park, 2.7km from Lincoln Park Zoo and 5.5km from the 360 Chicago Observation Deck, offering easy access to Fullerton Beach and Wrigley Field. The 325 square metre property boasts six bedrooms, two bathrooms, sleeps 10-20 guests, and includes a garden, tennis court, parking, and a balcony; nearby activities include fishing.
10 4 reviews
Oak Park, IL
06/09 – 07/09
$142/nightfor 1 night
Lower Level Luxury
2 2
apartment , Chicago
This Chicago flat is located in a prime district, offering convenient access to major landmarks and attractions. This family-friendly 255 square meter apartment features one bedroom, one bathroom, air conditioning, WiFi, and a kitchenette, accommodating up to seven guests with private check-in and check-out.
9.9 158 reviews
Oak Park, IL
10/07 – 12/07
$2621/nighttotal: $5242 (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.
Best Oak Park, IL vacation rentals with parking
10 2 reviews
Oak Park, IL
17/07 – 27/07
$419/nighttotal: $4190 (10 )
Mid-century Posh Meets Urban Charm
1 1
apartment , Oak Park
This 2-bedroom, 1-bathroom flat is located in a well-connected district of Oak Park, offering convenient access to local attractions and business areas. This fully equipped apartment accommodates up to 6 guests, providing a comfortable, home-away-from-home experience with extras in the kitchen and bathroom, ideal for both business and leisure stays.
Oak Park, IL
28/06 – 05/07
$507/nighttotal: $3549 (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 6 reviews
Oak Park, IL
28/06 – 05/07
$578/nighttotal: $4046 (7 )
Comfy 3br Chicago Retreat 420 Friendly Unit Near Mccormick Place & Soldier Field
3 5
apartment , Chicago
This three-bedroom apartment is situated in Chicago's South Loop, a 7-9 minute walk from McCormick Place convention centre and a 5-6 minute walk from a Green Line station, offering easy access to the Field Museum, Shedd Aquarium, and Adler Planetarium. The 107 square metre (1150 square foot) property sleeps six, features a fully equipped kitchen with dishwasher, in-unit laundry, 250 Mbps internet, and optional daily parking for £23 (approx. $30 USD).
Oak Park, IL
25/06 – 25/07
$457/nighttotal: $13710 (30 )
Modern 3br Apt Near United Center
3 3
apartment , Chicago
This Lawndale flat is situated in a secure district, offering a 10-minute drive to the United Center, a 15-minute drive to Cook County Hospital, and a 15-minute drive to downtown Chicago. This 3-bedroom, 2-bathroom residence accommodates up to 6 guests and features in-unit laundry, a flat-screen TV, and a coffee machine, with Grant Park and Lake Michigan within easy reach for outdoor pursuits.
Frequently Asked Questions about vacation rentals in Oak Park, IL
What should a first-time visitor not miss in Oak Park, IL?
A first-time visitor to Oak Park should definitely check out the Frank Lloyd Wright Trust sites, like the iconic Unity Temple and the beautiful Home and Studio. You can't go wrong with a stroll down the charming streets of the village, and a visit to the Oak Park Public Library is a must for any book lover.
What are the best Airbnb and vacation rentals in Oak Park, IL?
Which neighborhood in Oak Park, IL should you consider for a vacation rental?
The village is pretty compact, but if you want to be close to the action, consider the area around the Oak Park Avenue and Lake Street intersection. It's close to the train station, shops, restaurants, and the vibrant downtown area.
What are the most popular Airbnbs in Oak Park, IL?
What are the top family-friendly attractions in Oak Park, IL?
Oak Park has plenty for families! The park district has fantastic playgrounds, like the one at Scoville Park. The Oak Park Conservatory is a great place for a family outing, and the nearby Brookfield Zoo is always a hit with kids.
What are the best vacation rentals with a pool 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 usually during the shoulder seasons, from April to May and September to October, when the weather is mild and the crowds are smaller. Prices tend to be lower during these months too.
What are the best rentals for families and kids in Oak Park, IL?
What events or festivals should visitors check out in and around Oak Park, IL?
Oak Park has a lively events calendar! The Oak Park Festival of the Arts is a highlight in July, and the annual Taste of Oak Park is a great way to sample local cuisine. You can also catch the vibrant farmers' market at the Oak Park Public Library.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?
What are the best budget-friendly activities in Oak Park, IL?
Oak Park is great for budget-conscious travellers. Take a stroll through the beautiful residential streets and admire the architecture, visit the free Oak Park Public Library, or enjoy a picnic in one of the many parks. There are also several free events throughout the year.
What are the best restaurants with local dishes in Oak Park, IL?
For local fare, head to Maya Del Sol for authentic Mexican cuisine or try the classic American dishes at The Purple Pig. If you're looking for something more casual, grab a pizza at the popular Lou Malnati's Pizzeria.
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 village is known for its beautiful tree-lined streets, so a walk along Forest Avenue or a bike ride along the Des Plaines River Trail is a must. There's also a paved trail along the Chicago Sanitary and Ship Canal.
Are there pet-friendly attractions in Oak Park, IL?
Oak Park is very dog-friendly! Most parks welcome dogs on leash, and many restaurants have outdoor seating where you can enjoy a meal with your furry companion. The Oak Park Conservatory also has a dog-friendly area.
What are the benefits of choosing a vacation rental in Oak Park, IL?
Vacation rentals offer more space and privacy compared to hotels. They are also often more affordable, especially for larger groups or families. You can also enjoy the convenience of having a kitchen and laundry facilities.
What are the top sports attractions and facilities in Oak Park, IL?
Oak Park is home to the Oak Park and River Forest High School, which boasts a state-of-the-art athletic complex. The village also has a number of public parks with sports fields and courts, and the nearby Ridgeland Common offers a variety of recreational activities.
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.
9.7 826 reviews
Oak Park, IL
17/07 – 27/07
$813/nighttotal: $8130 (10 )
Mich Ave Downtown 2bd, Grant Park Museums #25
2 1
apartment , Chicago
This Chicago apartment is located in the Grant Park district, a short walk from the Museum Campus, Soldier Field, and Grant Park, making it ideal for exploring the city's cultural attractions. The apartment has received excellent ratings for location, cleanliness, and user experience. The apartment is a spacious two-bedroom flat with two bathrooms, comfortably accommodating up to six guests. The apartment has a fully equipped kitchen, a balcony, a garden, and parking, offering a comfortable and convenient stay.
10 53 reviews
Oak Park, IL
11/10 – 21/10
$642/nighttotal: $6420 (10 )
Chic Urban Retreat Near Wrigley Field W/parking
2 2
apartment , Chicago
This Lakeview/Southport flat is situated a short distance from Wrigley Field, offering easy access to Lake Michigan and other Chicago attractions. The 111-square-metre (1194 square feet) property boasts two bedrooms, two bathrooms, and sleeps six, including a fully equipped kitchen, high-speed Wi-Fi, air conditioning, laundry facilities, and complimentary parking.
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.
Best Oak Park, IL vacation rentals with air conditioning
10 14 reviews
Oak Park, IL
28/06 – 05/07
$331/nighttotal: $2317 (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.
10 315 reviews
Oak Park, IL
06/09 – 07/09
$1572/nightfor 1 night
Urban Luxury 1br/2ba Logan Square Condo W/garage
1 2
apartment , Chicago
This one-bedroom flat is situated in the Logan Square district, a 1.6 km walk from the Logan Square Monument and a short distance from the Logan Square Blue Line Station, providing easy access to Chicago's city centre. The property boasts a large garden with a patio and fire pit, perfect for relaxing, and comes with a fully equipped kitchen, a Jacuzzi, free on-site parking, and high-speed Wi-Fi.
9.9 108 reviews
Oak Park, IL
06/09 – 07/09
$1285/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.
10 3 reviews
Oak Park, IL
28/06 – 03/07
$390/nighttotal: $1950 (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.
