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Best Short term and Weekly rentals in Oak Park, IL
9.3 3 reviews
Oak Park, IL
06/28 – 07/03
$258/nighttotal: $1290 (5 )
Wonderful 1br Retreat With Balcony In Oak Park
1 2
apartment , Oak Park
This 2-bedroom, 2-bathroom apartment in Oak Park offers comfortable accommodations for up to 4 guests, featuring a stylish interior, a garden, and a fitness center, with convenient access to Oak Park's renowned landmarks. This well-appointed residence includes a full kitchen with a fridge, freezer, microwave, and dishwasher, along with air conditioning and internet, making it ideal for group travel and exploring the community.
9.6 301 reviews
Oak Park, IL
07/17 – 07/27
$95/nighttotal: $950 (10 )
Comfortable Room With Easy Access To Chicago
1 1
apartment , Oak Park
This charming bed and breakfast is located just south of Oak Park in Berwyn, a quiet suburb with easy access to downtown Chicago via the train station just six blocks away. Guests consistently praise the property's excellent location, cleanliness, and overall experience. The apartment features a unique loft design, providing a spacious feel with a queen-sized bed and a private bathroom. Guests can enjoy amenities like a fully equipped kitchen, laundry access, a community table, and a TV with Firestick, as well as the friendly cats and the owner's warm hospitality.
9.9 227 reviews
Oak Park, IL
06/28 – 07/05
$270/nighttotal: $1890 (7 )
The Evergreen House
1 5
apartment , Chicago
This comfortable Chicago apartment is located in a quiet neighborhood, offering easy access to public transportation and major highways. It consistently receives excellent ratings for cleanliness, location, and overall guest experience. The apartment has two bedrooms and one bathroom, comfortably accommodating up to five guests. Amenities include free street parking, a private backyard, a fully equipped kitchen, a washer and dryer, and three televisions with Wi-Fi and Netflix.
9.9 31 reviews
Oak Park, IL
06/28 – 07/05
$252/nighttotal: $1764 (7 )
Modern & Comfy Gem Near Transit
1 5
apartment , Chicago
This 3-bedroom East Garfield Park residence is minutes from the Garfield Park Conservatory and offers convenient public transit access for exploring Chicago. This apartment accommodates up to 7 guests with a fully equipped gourmet kitchen, central air conditioning, high-speed Wi-Fi, and Smart TVs in all bedrooms.
9.9 88 reviews
Oak Park, IL
07/17 – 07/27
$385/nighttotal: $3850 (10 )
Appartement-d'exception-salle De Bain Privée-vue S
3 1
apartment , Oak Park
This three-bedroom apartment is located in Historic Oak Park, just three blocks from the L-line, next to Hemingway's birthplace, and within walking distance of Frank Lloyd Wright studios. The apartment has received excellent user, location, and cleanliness ratings. The 1,800 square foot apartment can accommodate up to six guests with a spacious dining room, living room, top-of-the-line kitchen, generous office space, and inviting TV room. The apartment also offers amenities like air conditioning, a garden, parking, high-speed internet, and two garages.
10 2 reviews
Oak Park, IL
07/10 – 07/12
$6000/nighttotal: $12000 (2 )
Private Inn And Event Space
1 14
B&B , Chicago
The Ruby Room, a boutique inn in Chicago's Wicker Park neighborhood, offers easy walking access to the area's restaurants and bars. This Chicago guesthouse features eight bedrooms, ten bathrooms, and accommodates up to sixteen guests, boasting luxurious king rooms with marble baths, a serene garden, stylish event spaces, and a spa-like atmosphere—note the absence of televisions.
9.7 158 reviews
Oak Park, IL
06/25 – 07/25
$159/nighttotal: $4770 (30 )
Kng + Qn 2bdrm/1 Free Parking By O’hare/allstate
1 3
apartment , Melrose Park
This Melrose Park apartment is conveniently located near Oak Park and O'Hare International Airport, offering easy access to both downtown Chicago and the airport. It has consistently received excellent ratings for its cleanliness, location, and overall user experience. The apartment features two bedrooms and one bathroom, comfortably accommodating up to four guests. It comes equipped with a full kitchen, air conditioning, parking, and internet access, ensuring a comfortable and convenient stay.
9.2 49 reviews
Oak Park, IL
09/06 – 09/07
$322/nightfor 1 night
The Polo Inn Bridgeport U.s.a.
2 2
B&B , Chicago
This Chicago bed and breakfast is located just six miles south of the city center, close to U.S. Cellular Field and McCormick Place, offering easy access to both major attractions and the city's heart. This property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. Each suite features a unique design, a full-size refrigerator, a flat-screen cable TV, and fingerprint security locks for added safety. Guests can enjoy a complimentary breakfast voucher, free parking, and shuttle service to McCormick Place and nearby train stations.
9.5 21 reviews
Oak Park, IL
06/25 – 07/25
$174/nighttotal: $5220 (30 )
Lory’s Cozy Place! Safe,convinient,15 Min To Loop!
3 3
apartment , Chicago
This 3-bedroom apartment is conveniently located near the Central Park Pink Line train station, providing easy access to the Chicago Loop in just 15 minutes. Guests have consistently rated the apartment excellent for location, cleanliness, and overall experience. The apartment has one bathroom and comfortably sleeps up to 5 guests. It includes amenities such as free Wi-Fi, a fully equipped kitchen, air conditioning, and a private garden. You can also enjoy free street parking or opt for private parking for an additional fee.
Oak Park, IL
06/28 – 07/03
$278/nighttotal: $1390 (5 )
The King's Corner / Ground Level / Train Access
1 2
apartment , Oak Park
This Oak Park studio apartment is conveniently located 0.6 miles from the Frank Lloyd Wright district and 0.8 miles from the Ernest Hemingway Museum and House, with two nearby metro stations offering access to Chicago attractions. This rental includes a kitchenette, air conditioning, on-site parking, and accommodates up to two guests.
Oak Park, IL
07/10 – 07/12
$1095/nighttotal: $2190 (2 )
Four Pet-friendly 1br Suites, Free Airport Shuttle
4 14
B&B , Schiller Park
Located just 3 minutes from O'Hare International Airport, this B&B is the perfect place to stay for travelers visiting Schiller Park. The B&B has 4 bedrooms and 4 bathrooms, and can accommodate up to 16 guests. Guests can enjoy a variety of amenities, including a fitness center, free WiFi, and a complimentary airport shuttle. The B&B is also conveniently located within walking distance of Oak Hill Park, Kampen Family Aquatic Center, and Rosewood Park. A short drive will take you to Brookfield Zoo, White Pines Golf Course, and Schiller Theater. In-room amenities include microwaves, refrigerators, and coffee makers. The B&B also offers a 24-hour fitness center, complimentary WiFi, and a business center. Self-parking is available with low extra fees, and complimentary coffee is served in the lobby.
9.9 31 reviews
Oak Park, IL
06/28 – 07/05
$218/nighttotal: $1526 (7 )
Modern 2 Bd Near The 606 Trail | W&d | Luxtel
1 5
apartment , Chicago
This centrally located Chicago apartment offers easy access to the city's attractions, though the specific neighborhood isn't disclosed. The ground-floor unit features two queen beds (one with a Purple mattress), a sleeper sofa, a fully equipped kitchen with Samsung appliances, a 55" smart TV with Netflix, and accommodates up to six guests.
Search Luxury Short-Term Rentals in Oak Park, IL
Experience the pulse of the city from a luxury rental in central Oak Park, IL, where every urban convenience is at your fingertips.
9.6 265 reviews
Oak Park, IL
07/17 – 07/27
$446/nighttotal: $4460 (10 )
The Neighborhood Hotel-little Italy
1 1
aparthotel , Chicago
This 3.5-star Chicago Near West Side apartment hotel is located less than a mile from Rush University Medical Center and within three miles of the United Center and Millennium Park, offering easy access to public transportation. Each apartment features a kitchenette with a refrigerator, stovetop, microwave, and dishwasher, plus a smart TV with satellite channels, a sitting area, and coffee/tea maker; on-site laundry facilities are also available.
9.4 3083 reviews
Oak Park, IL
07/17 – 07/27
$492/nighttotal: $4920 (10 )
Kasa South Loop Chicago
1 1
aparthotel , Chicago
Kasa South Loop Chicago is located in the South Loop neighborhood, just a short walk from DePaul University and a quick drive from attractions like Willis Tower and the Art Institute of Chicago. The aparthotel has excellent ratings for location, cleanliness, and overall user experience. The apartments are spacious and well-equipped with kitchens, seating areas, and private bathrooms. Guests can enjoy amenities like a swimming pool, fitness center, and a sun terrace, along with free Wi-Fi and a business center.
9.2 1381 reviews
Oak Park, IL
06/28 – 07/05
$637/nighttotal: $4459 (7 )
Kasa Magnificent Mile Chicago
2 5
aparthotel , Chicago
Kasa Magnificent Mile Chicago is located on the Magnificent Mile, a bustling shopping and dining district, just a short walk from the Shops at Northbridge, CIBC Theatre, and Millennium Station. This aparthotel boasts excellent user ratings for its location, cleanliness, and overall experience. The apartment features modern amenities like a flat-screen TV, air conditioning, and a private bathroom. Guests can enjoy a terrace or balcony, a garden, a fitness center, and a restaurant.
Best Oak Park, IL Short term rentals with a jacuzzi
Among the 233 accommodations in Oak Park, IL, here are the 4 best rentals with a jacuzzi
10 315 reviews
Oak Park, IL
09/06 – 09/07
$1125/nightfor 1 night
Urban Luxury 1br/2ba Logan Square Condo W/garage
1 2
apartment , Chicago
This one-bedroom garden-level condo is located in Logan Square, just one block from the Logan Square Blue Line station and a short walk from the neighborhood's restaurants and nightlife. The apartment offers free on-site garage parking, a fully equipped kitchen, and a spacious backyard with a patio and fire pit.
9.1 68 reviews
Oak Park, IL
06/28 – 07/03
$966/nighttotal: $4830 (5 )
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile
2 2
apartment , Chicago
This apartment is located in the heart of the Magnificent Mile, a short walk from Oak Street Beach and Ohio Street Beach, making it ideal for exploring Chicago's vibrant downtown and relaxing by the lake. The apartment has excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The apartment is fully furnished and equipped with a kitchen, making it perfect for families or groups. Amenities include a rooftop pool, free Wi-Fi, and private parking, offering a range of options for relaxation and entertainment.
10 3 reviews
Oak Park, IL
06/28 – 07/03
$912/nighttotal: $4560 (5 )
Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12
3 2
apartment , Chicago
This West Town Chicago apartment boasts a prime location, just five minutes from Fulton Market's restaurants and the United Center, and seven minutes from Grant Park and Michigan Avenue. The three-bedroom, three-bathroom unit sleeps up to twelve guests and features a king suite with a fireplace and steam shower, a queen suite with private roof deck access, a fully stocked kitchen with a balcony, super-fast WiFi, a private car garage, and a fenced-in backyard; enjoy stunning Willis Tower views from the roof deck.
Oak Park, IL
07/17 – 07/27
$1680/nighttotal: $16800 (10 )
The Bernadin- Designer 3br City Center With Balcony
3 1
apartment , Chicago
This casino-equipped condo is located centrally in Chicago, a 17-minute walk from Oak Street Beach and close to Water Tower Chicago, 360 Chicago, and the Museum of Contemporary Art. This 1600 square foot, 3-bedroom residence accommodates up to 9 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a swimming pool, jacuzzi, garden, and fitness center.
Frequently Asked Questions about short term rentals in Oak Park, IL
Which top landmarks you shouldn't miss in Oak Park, IL?
Oak Park is known for its beautiful architecture, so definitely check out Frank Lloyd Wright's Home and Studio, the Unity Temple, and the Pleasant Home. You can also wander through the historic districts to see other beautiful homes.
What are the best short term rentals in Oak Park, IL?
What kind of weather can travelers expect in Oak Park, IL?
Oak Park has a humid continental climate, so you can expect hot, humid summers and cold, snowy winters. Spring and fall are usually mild and pleasant, perfect for exploring the town.
What are the best short term rentals with a pool in Oak Park, IL?
What are the most popular festivals and events in Oak Park, IL?
Oak Park has a lot going on! The Oak Park Festival of the Arts is a big one in June, and the Oak Park Music Festival in August is always popular. The farmers market is also a great place to visit on Saturdays during the summer.
What are the best short term rentals with a jacuzzi in Oak Park, IL?
Are there any famous stadiums or sports arenas in Oak Park, IL?
Oak Park doesn't have any major stadiums or sports arenas, but there are some great places to catch a game in nearby Chicago, like Wrigley Field or Guaranteed Rate Field.
What are the best short term rentals for families and kids in Oak Park, IL?
What part of Oak Park, IL is ideal for finding lodging?
The downtown area near the Oak Park Avenue and Lake Street intersection is a great place to stay. You'll be close to shops, restaurants, and public transportation.
Destinations nearby
Discover Family Short-Term Rentals in Oak Park, IL
Family trips to Oak Park, IL are made simple with urban rentals that keep city attractions within easy walking distance.
10 4 reviews
Oak Park, IL
09/06 – 09/07
$102/nightfor 1 night
Lower Level Luxury
2 2
apartment , Chicago
This Chicago apartment is located in a district with convenient access to local attractions and amenities. This spacious 2740 square foot residence offers a 1-bedroom layout, accommodating up to 7 guests with a fully equipped kitchenette, complimentary WiFi, and an outdoor seating area.
10 1 review
Oak Park, IL
06/28 – 07/03
$286/nighttotal: $1430 (5 )
South Loop 2br Chicago 420-friendly Near Mccormick & Chinatown
2 2
apartment , Chicago
This South Loop apartment is situated near McCormick Place and Chinatown, offering convenient access to Chicago landmarks such as the Field Museum and the Art Institute of Chicago, all within 1.6 to 2.1 miles. This family-friendly rental features a fully equipped kitchen, air conditioning, a private terrace, and on-site parking, accommodating up to 11 guests with complimentary WiFi.
9.8 39 reviews
Oak Park, IL
06/28 – 07/03
$192/nighttotal: $960 (5 )
Artful Abode: Cozy & Stylish Stay
1 2
apartment , Berwyn
This Berwyn apartment rental boasts a convenient location near Midway and O'Hare International Airports, offering a quick 20-minute commute to downtown Chicago. The two-bedroom, one-bathroom unit sleeps six guests and features a fully equipped kitchen, internet access, and a unique artistic interior design.
9.9 165 reviews
Oak Park, IL
09/06 – 09/07
$608/nightfor 1 night
Eddy Street Upstairs Apartment
1 2
B&B , Chicago
This one-bedroom apartment is located in the Portage Park neighborhood of Chicago, about 25 minutes from downtown and 20 minutes from O'Hare Airport, offering a quiet and convenient location. It has received excellent ratings for cleanliness, location, and overall user experience. The apartment comfortably accommodates up to five guests with a queen bed, a comfy couch, and an additional queen air mattress. Guests can enjoy amenities like a shared washer and dryer, a kitchen with a fridge, freezer, and microwave, and a fitness center.
Best Oak Park, IL lodging with parking
9.4 21 reviews
Oak Park, IL
07/17 – 07/27
$248/nighttotal: $2480 (10 )
Comfy Bed/free Parking&wifi /Nearhosp/ord/mdw/dt
1 1
apartment , Oak Park
This apartment is located in Berwyn, a short drive from Oak Park and just a 25-minute drive from downtown Chicago. The property has earned an excellent user rating, making it a popular choice for travelers. This one-bedroom unit comfortably accommodates up to 5 guests. The apartment features a fully equipped kitchen, free Wi-Fi, parking, and is close to local attractions, including restaurants and gambling slot machines.
8.0 1 review
Oak Park, IL
09/06 – 09/07
$479/nightfor 1 night
Mins To Dt & Frank Lloyd Wright
1 2
apartment , Oak Park
This 1-bedroom rental in Oak Park is located adjacent to Petersen's Ice Cream and Broken Tart, a 4-minute walk from the Frank Lloyd Wright Home and Studio, and a 10-minute walk from Downtown Oak Park. This pet-friendly apartment sleeps up to 4 guests and offers a full kitchen with a fridge and microwave, air conditioning, a garden, and parking, with optional early check-in and late check-out services available.
8.0 1 review
Oak Park, IL
06/25 – 07/25
$310/nighttotal: $9300 (30 )
Walkable Downtown Forest Park Apartment
1 3
apartment , Forest Park
This vintage bungalow is located in a quiet residential block of Forest Park, a few blocks from Madison Street's dining and shopping, and offers easy access to downtown Chicago. This 2-bedroom, 1-bathroom rental sleeps 4 guests and features hardwood floors, a sunroom, a private backyard, WiFi, a dishwasher, and parking for one vehicle.
9.2 298 reviews
Oak Park, IL
07/17 – 07/27
$382/nighttotal: $3820 (10 )
1br Modern Apartment In Lincoln Square - Eastwood 3s Rep
1 1
apartment , Chicago
This Chicago apartment is conveniently located in the Ravenswood district, just a short distance from Lincoln Park Zoo and United Center, offering easy access to attractions and public transportation. The apartment consistently receives excellent ratings for its cleanliness, location, and overall user experience. The apartment features two bedrooms and a fully equipped kitchen, providing ample space for a comfortable stay. Guests can enjoy amenities like free Wi-Fi, air conditioning, a dishwasher, and parking, making it ideal for both short and long-term stays.