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Best Short term and Weekly rentals in Oak Park, IL
9.8 51 reviews
Oak Park, IL
06/28 – 07/03
$162/nighttotal: $810 (5 )
Serene One Bedroom One Bath Apartment Near Chicago
1 2
apartment , Forest Park
This Forest Park apartment rental is conveniently located near public transportation, the Interstate 290, and is within 8 miles of downtown Chicago, Oak Park, River Forest, and Oak Brook Mall. The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen (fridge, freezer, microwave), air conditioning, a private garden, parking, and access to nearby tennis courts.
9.4 449 reviews
Oak Park, IL
06/28 – 07/03
$252/nighttotal: $1260 (5 )
Cabin 201 By 747 Lofts
1 2
apartment , Chicago
This studio apartment is conveniently located near the Blue Line L station, making it easy to explore both downtown Chicago and the trendy West Loop neighborhood with its many restaurants, bars, and shops. The apartment has received excellent ratings for location, cleanliness, and overall user experience. The studio has a modern kitchen, in-unit laundry, and a spa-like bathroom, offering a comfortable and convenient stay for up to 3 guests. You'll also enjoy easy access to top restaurants, bars, and shops, all within walking distance.
9.4 42 reviews
Oak Park, IL
07/17 – 07/27
$290/nighttotal: $2900 (10 )
Explore Chicago! | King Bd Near Train | Near Shops
1 1
apartment , Oak Park
This Oak Park apartment rental is conveniently located a short walk from the Green Line CTA train and Historic Downtown Oak Park, offering easy access to Frank Lloyd Wright's architecture and major medical centers. The first-floor unit, accessible by elevator or a short flight of stairs, features a king-size bed, 50-inch smart TV, fully equipped kitchen, and accommodates two guests; free parking passes (up to 3) are included.
9.9 59 reviews
Oak Park, IL
07/17 – 07/27
$222/nighttotal: $2220 (10 )
Restored Mid-century 4 Square
1 1
apartment , Oak Park
This Oak Park apartment rental offers easy access to downtown Oak Park's shops and restaurants, and is a short drive or public transportation ride from Chicago attractions. The first-floor unit features a spacious four-room layout with a king-size bed, sofa sleeper, full kitchen including a dishwasher, and off-street parking, comfortably sleeping four guests.
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.
9.7 69 reviews
Oak Park, IL
06/25 – 07/25
$253/nighttotal: $7590 (30 )
Exquisite Rogers Park 1bd/1bath Apt. Near Evanston
1 3
apartment , Chicago
This apartment is located in Rogers Park, a diverse neighborhood just a short drive from the Howard Station, which connects you to the Red, Yellow, and Purple Lines for easy access to the city. It's also close to Evanston and Northwestern University, making it a great choice for those looking to explore the area. The apartment boasts excellent ratings for location, cleanliness, and user satisfaction. The apartment has one bedroom and one bathroom, comfortably accommodating up to 3 guests. It offers modern finishes, a well-equipped kitchen with a fridge and microwave, air conditioning, parking, and shared laundry facilities. This apartment is perfect for families or small groups looking for a comfortable and convenient stay in Chicago.
9.9 87 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.
9.6 21 reviews
Oak Park, IL
07/10 – 07/12
$3880/nighttotal: $7760 (2 )
:: The Wolcott :: Modern Elegance At Its Finest
6 14
apartment , Chicago
This exquisite 6,000-square-foot single-family home is located in Chicago's Wicker Park neighborhood, offering easy access to the area's restaurants, shops, and public transportation. The spacious residence boasts four ensuite bedrooms, additional sleeping space for eight, a custom kitchen with Bosch and Thermador appliances, a private backyard, rooftop decks with Chicago skyline views, a wine cellar, pool table, and fitness room, accommodating up to sixteen guests.
9.2 64 reviews
Oak Park, IL
07/17 – 07/27
$258/nighttotal: $2580 (10 )
Charming Loft: King Bd/elevator/train/bus/shops
1 1
apartment , Oak Park
This cozy Oak Park loft is located a short walk from Historic Downtown Oak Park, offering easy access to shops and restaurants. The one-bedroom, one-bathroom unit sleeps three guests comfortably, featuring a king-size bed, 50-inch smart TV, fast Wi-Fi, a fully equipped kitchen, and weekly/monthly discounts.
9.8 152 reviews
Oak Park, IL
07/10 – 07/12
$3800/nighttotal: $7600 (2 )
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
6 14
apartment , Chicago
Loft606 Chicago is a 5,307 sq. ft. loft located in the heart of Chicago's Wicker Park neighborhood, just a short walk from the 606 Bloomingdale Trail and the Blue Line CTA station. With excellent user, location, and cleanliness ratings, this apartment offers a unique and appealing experience for guests visiting Chicago. The apartment features a massive open space with a 26' timber beamed ceiling and skylights, accommodating up to 20+ guests with 7 bedrooms, 11 beds, and 2 large couches. Guests can enjoy a state-of-the-art gourmet kitchen, full-size bar, fireplace, and sound system, as well as a garden patio and rooftop deck for outdoor relaxation. The apartment also includes a fitness center, tennis court, spa, and three off-street parking spots.
10 12 reviews
Oak Park, IL
06/25 – 07/25
$176/nighttotal: $5280 (30 )
Top Floor Irving Park Chicago Great Location!
1 3
apartment , Chicago
This newly remodeled, top-floor condo is located in Chicago's Irving Park neighborhood, offering a peaceful and centrally-located base for exploring the city's attractions. This 2-bedroom, 1-bathroom residence accommodates up to 4 guests and features air conditioning, internet, and a kitchen, with access to a shared backyard in a quiet building.
Oak Park, IL
07/10 – 07/12
$1117/nighttotal: $2234 (2 )
4 Units | River North Location | Parking
4 14
B&B , Chicago
This Chicago bed and breakfast is located in the River North district, offering convenient access to the Magnificent Mile for shopping and dining, and is within 1,000 feet of Navy Pier. This B&B accommodates up to 16 guests across four bedrooms and features amenities such as internet, air conditioning, a year-round indoor heated swimming pool, a fitness center, and on-site parking.
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 3084 reviews
Oak Park, IL
06/28 – 07/05
$599/nighttotal: $4193 (7 )
Kasa South Loop Chicago
2 5
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 1379 reviews
Oak Park, IL
07/17 – 07/27
$420/nighttotal: $4200 (10 )
Kasa Magnificent Mile Chicago
1 1
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
Oak Park, IL
08/10 – 08/15
$1139/nighttotal: $5695 (5 )
Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park
5 2
apartment , Chicago
This spacious 2,200 sq ft luxury residence is situated in Chicago's Portage Park neighborhood, offering 5 bedrooms and 3 bathrooms for up to 16 guests, located 8-10 miles from downtown attractions such as Millennium Park and Skydeck Chicago. This family-friendly apartment features a dedicated entertainment basement with a home theater and arcade, a hot tub, a gym, and is close to local dining and shopping.
10 111 reviews
Oak Park, IL
07/10 – 07/12
$3934/nighttotal: $7868 (2 )
Luxurious Four-level Home With Personal Touches Everywhere
6 14
apartment , Chicago
This apartment is located in the Lakeview neighborhood, just steps from Wrigley Field, the Lake, Zoo, 606, and Southport Corridor. With excellent user, location, and cleanliness ratings, this 6-bedroom apartment can accommodate up to 16 guests in its 5010 square feet of floor area. The apartment features a chef's kitchen with a dazzling center island, a private courtyard and balcony on each level with skyline views, an outdoor fire pit for cozy evenings, a Jacuzzi, a sauna, a spa, a fitness center, and parking. It is also family-friendly, pet-friendly, and has internet access.
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 34 reviews
Oak Park, IL
06/28 – 07/03
$362/nighttotal: $1810 (5 )
Calm+stylish Oak Park Garden Apt 20min To Downtown
1 2
apartment , Oak Park
This Oak Park garden apartment is situated on a quiet cul-de-sac, minutes from downtown Oak Park, the Arts District, and Frank Lloyd Wright sites, offering easy access to public transportation (Green Line/Metra) and major highways (Highway 290). This fully renovated three-bedroom rental boasts a modern-vintage design, a private garden entrance, in-unit laundry, high-speed WiFi, and a spacious backyard with a retro camper, accommodating up to five guests.
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.
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.
9.4 3 reviews
Oak Park, IL
08/10 – 08/15
$1136/nighttotal: $5680 (5 )
8 Bedrooms, 3 Full Bathrooms, 2 Kitchens And 2 Parking Spaces
8 2
apartment , Oak Park
This Oak Park vacation home, near the Green and Blue CTA lines, provides easy access to downtown Chicago (approximately a 15-minute drive without traffic) and is within walking distance of local shops and restaurants. This 3200-square-foot residence features two separate apartments, sleeping up to 12 guests across eight bedrooms and three bathrooms, complete with a fully fenced backyard, ample parking, and convenient amenities including a dishwasher, microwave, and air conditioning.
Oak Park, IL
06/28 – 07/05
$401/nighttotal: $2807 (7 )
Skyline View 3br/2ba Family Heaven With Optional Parking
3 5
apartment , Chicago
This Near South Side Chicago apartment, a short walk from State Street and McCormick Place, offers easy access to Soldier Field and Lake Michigan (all within 2 miles). The 1100-square-foot unit features three bedrooms, two bathrooms, sleeps eight, and includes a fully equipped kitchen, free Wi-Fi, a patio, and on-site fitness center.
8.8 5 reviews
Oak Park, IL
06/28 – 07/05
$334/nighttotal: $2338 (7 )
Great Location. 5min To Mccormick Place. Downtown. Chinatown
3 5
apartment , Chicago
This Bridgeport apartment rental is conveniently located near Chinatown, a short five-minute drive from McCormick Place, Guaranteed Rate Field, and downtown Chicago. The three-bedroom, one-bathroom unit sleeps eight guests and features a full kitchen with dishwasher, in-unit laundry, a private backyard with cornhole, and free street parking; nearby attractions include the Willis Tower and Cloud Gate.
Best Oak Park, IL lodging with parking
8.8 26 reviews
Oak Park, IL
07/17 – 07/27
$146/nighttotal: $1460 (10 )
2br Airy & Tidy Apt With Free Covered Parking - Central Modern
1 1
apartment , Chicago
This Chicago apartment is conveniently located about 8 miles from Lincoln Park Zoo and Loyola University Chicago, making it a great choice for travelers interested in exploring those areas. It has received very good user ratings and excellent ratings for location and cleanliness. The apartment features two bedrooms, perfect for families or groups. Guests will enjoy amenities like free covered garage parking, a fully equipped kitchen, a washing machine, free Wi-Fi, and streaming services on the TV.
Oak Park, IL
07/17 – 07/27
$208/nighttotal: $2080 (10 )
The Urban Oasis
1 1
apartment , Chicago (IL)
Apartment listing. You will stay in Chicago (IL). Services and facilities: air conditioning, a kitchen and an iron. Enjoy free parking with this accommodation in Chicago (IL)!
9.8 8 reviews
Oak Park, IL
06/28 – 07/05
$370/nighttotal: $2590 (7 )
Archer #2 | New 3 Bedroom Near Mccormick Place, Wintrust Arena, Chinatown
3 5
apartment , Chicago
This 3-bedroom, 2-bathroom apartment is located near McCormick Place, Downtown, and Chinatown, offering easy access to Chicago's attractions. It has excellent user, location, and cleanliness ratings. The 900-square-foot apartment features a modern and inviting decor with comfortable memory foam mattresses and a spacious living area. It comes with amenities such as high-speed Wi-Fi, smart TVs, and a well-stocked kitchen. Guests can also enjoy the convenience of in-unit laundry, complimentary toiletries, and a laptop-friendly workspace.
10 66 reviews
Oak Park, IL
06/28 – 07/03
$435/nighttotal: $2175 (5 )
Oak Park - Wine House!
1 2
apartment , Oak Park
This Oak Park house, a newly remodeled single-family home, is ideally located a two-minute walk from the Blue Line EL station and 30 steps from Buzz Cafe, with several highly-rated restaurants, including Mora Sushi and Publican Bread, within a block. The three-bedroom, one-bathroom residence comfortably sleeps six, features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and internet access; guests can enjoy easy access to Chicago via public transportation.