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Best Vacation rentals and Airbnb offers in Oak Park, IL
9.9 43 reviews
Oak Park, IL
10/11 – 10/21
$188/nighttotal: $1880 (10 )
Large Unit In Prime Logan Square
1 2
apartment , Chicago
This garden-level unit is located in Chicago's Logan Square neighborhood, offering private entrance access and placing you a short walk from the 606 trail and numerous dining and bar options. This one-bedroom, one-bathroom apartment accommodates up to three guests and features a full kitchenette, smart lock entry, air conditioning, and free street parking.
10 252 reviews
Oak Park, IL
06/28 – 07/03
$236/nighttotal: $1180 (5 )
Chic Retreat In Historic Victorian House-park Free
1 2
apartment , Oak Park
This charming one-bedroom apartment is located in downtown Oak Park, just a short walk from public transportation, restaurants, shops, and grocery stores. Guests consistently rate this rental excellent for its location, cleanliness, and overall experience. This comfortable dwelling features a fully equipped kitchen, a clawfoot tub, and a shared veranda. Guests can enjoy free parking, laundry facilities, and a quiet location.
9.5 4 reviews
Oak Park, IL
07/10 – 07/12
$3097/nighttotal: $6194 (2 )
Six-bedrooms In Wrigleyville
1 14
apartment , Chicago
This Wrigleyville rental is steps from Wrigley Field and numerous restaurants in Chicago's nightlife district. This two-unit apartment sleeps sixteen guests, offering six bedrooms, two bathrooms, a shared deck, parking permits, and a full kitchen including a dishwasher and microwave.
10 17 reviews
Oak Park, IL
06/28 – 07/05
$354/nighttotal: $2478 (7 )
3 Bedroom Apartment, 15 Min Drive To Wrigley Field
1 5
apartment , Chicago
This 3-bedroom house in Chicago is conveniently located near Lincoln Square and Albany Park, with downtown Chicago accessible via CTA and Wrigley Field a 15-minute drive away. This family-friendly rental accommodates up to 5 guests with a fully equipped kitchen, in-unit laundry, air conditioning, and free street parking, offering a smart TV and board games for entertainment.
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 15 reviews
Oak Park, IL
07/10 – 07/12
$1895/nighttotal: $3790 (2 )
The Jackpot | Hot Tub · Cinema · Bar · Sleeps 14
6 14
apartment , Chicago
This 6-bedroom, 3-bathroom Chicago rental home offers excellent access to the city, with a 9-minute walk to the Blue Line providing a 13-mile drive to O'Hare Airport and a 16-mile drive to downtown, plus it's a 15-mile drive to Wrigley Field. This spacious vacation rental accommodates 14 guests and features a backyard oasis with a hot tub and fire pit, a game room with ping pong and foosball, a 120-inch 4K home theater, a sunroom, and a fully equipped kitchen, complemented by free garage parking for two vehicles.
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.
Oak Park, IL
07/10 – 07/12
$4546/nighttotal: $9092 (2 )
3 Stylish 2brs Steps From Magnificent Mile
1 14
apartment , Chicago
This Gold Coast Chicago rental comprises three luxurious apartments on floors 24, 25, and 26, offering stunning city views and proximity to Lake Michigan and its winter activities, including ice skating. Each 2-bedroom, 2-bathroom unit sleeps up to 5 guests, boasts private balconies, and provides access to a resort-style sundeck with a pool, a 2,600-square-foot fitness center, and extensive building amenities including a social club, gaming center, and meditation lounges.
9.4 54 reviews
Oak Park, IL
07/17 – 07/27
$266/nighttotal: $2660 (10 )
Urban Oasis: 1st Level/ King Bd/train/bus/shops
1 1
apartment , Oak Park
This first-floor Oak Park apartment, located a few blocks from Historic Downtown Oak Park, offers easy access to shops and restaurants. The one-bedroom unit sleeps two guests and features a king-size bed, 50-inch smart TV, fully equipped kitchen with microwave and coffee maker, and fast Wi-Fi; weekly and monthly discounts are available.
9.8 59 reviews
Oak Park, IL
08/10 – 08/15
$210/nighttotal: $1050 (5 )
A Luxury Stay While You're Away
1 2
apartment , Oak Park
This Oak Park apartment rental sleeps six guests and includes three bedrooms, two bathrooms, a kitchen, air conditioning, internet, parking, and allows pets. The unit offers ample space for a comfortable stay, boasting convenient amenities and a location in Oak Park, though precise address and proximity to landmarks requires further details.
9.8 39 reviews
Oak Park, IL
08/10 – 08/15
$164/nighttotal: $820 (5 )
Darling Flat Walk To Op
1 2
apartment , Oak Park
This newly remodeled Oak Park apartment rental is located within blocks of downtown Oak Park and the Green Line station, offering easy access to Chicago and proximity to Frank Lloyd Wright's architectural masterpieces. The one-bedroom, one-bathroom unit sleeps two guests and includes a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus in-unit laundry, air conditioning, and parking.
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.
Compare Vacation Rentals for Families in Oak Park, IL
These family-friendly vacation rentals in Oak Park, IL offer spacious layouts and easy access to top city attractions.
9.8 175 reviews
Oak Park, IL
07/17 – 07/27
$393/nighttotal: $3930 (10 )
Cozy, Comfortable And Convenient Apartment. Close To Everything!
2 1
apartment , Oak Park
This studio apartment is located in Oak Park's Arts District, just a short walk from the Frank Lloyd Wright Home and Studio. It has excellent user, location, and cleanliness ratings. The studio comfortably sleeps four guests and features a spacious 930 square foot layout. Amenities include a fully equipped kitchen, a private backyard patio, a spa, and secure parking.
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.
9.0 1119 reviews
Oak Park, IL
07/10 – 07/12
$3127/nighttotal: $6254 (2 )
The Hotel & Athletic Club At Midtown
6 14
resort , Chicago
The Hotel & Athletic Club at Midtown is located in Chicago's Midtown neighborhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The resort has received very good ratings for its location, cleanliness, and overall experience. This hotel offers spacious and modern rooms, each equipped with comfortable amenities. Guests can enjoy a wide range of activities and features, including a fitness center, swimming pool, spa, tennis courts, and a variety of dining options.
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 vacation rentals with parking
10 8 reviews
Oak Park, IL
06/28 – 07/03
$163/nighttotal: $815 (5 )
King Comfort Apartment, Quiet, Clean, Ac & Wifi
1 2
apartment , Chicago
This Austin, Chicago vacation rental is conveniently located near Humboldt Park and the Frank Lloyd Wright Historic District, within 3 miles, and offers easy access to the United Center (6 miles away). The one-bedroom, one-bathroom home sleeps three guests and includes a fully equipped kitchen with modern amenities such as a Smart TV and is close to the Chicago Grand-Cicero train station (7-minute walk).
8.0 3 reviews
Oak Park, IL
06/28 – 07/05
$438/nighttotal: $3066 (7 )
Spacious 3br Rogers Park Town House Budget-friendly
3 5
apartment , Chicago
This West Ridge Chicago townhome offers easy access to attractions like the Chicago Theatre, Art Institute of Chicago, Michigan Avenue, Navy Pier, Wrigley Field, and the United Center, though precise distances aren't provided. The three-bedroom, one-bathroom rental sleeps five guests comfortably, featuring one queen bed and two twin beds, air conditioning, Wi-Fi, and a relaxing bathtub.
10 9 reviews
Oak Park, IL
06/28 – 07/05
$372/nighttotal: $2604 (7 )
The Neighborhood Hotel - Little Italy Two Bedroom
2 5
apartment , Chicago
This stylish apartment in Chicago's Near West Side offers a unique mid-century Italian design with soaring ceilings and terrazzo-inspired floors. It's conveniently located near Navy Pier, Michigan Avenue, and other attractions, and has an excellent user rating. The apartment has two bedrooms, one bathroom, and can accommodate up to six guests. It features a well-equipped kitchenette, modern amenities like a smart TV and high-speed Wi-Fi, and a no-smoking policy for a fresh and clean environment.
9.8 5 reviews
Oak Park, IL
06/28 – 07/03
$255/nighttotal: $1275 (5 )
Chic 1 Br W Parking
1 2
apartment , Chicago
This one-bedroom Chicago apartment near the United Center offers easy access to the arena, Union Station, and attractions like the Cloud Gate, CIBC Theatre, and DePaul University. The 820-square-foot flat features a fully equipped kitchen, in-unit laundry, a private patio, free Wi-Fi, on-site casino access, and accommodates up to seven guests.
Frequently Asked Questions about vacation rentals in Oak Park, IL
When is the best time to book a vacation rental in Oak Park, IL?
You'll want to book your vacation rental in advance, especially during peak season, which runs from May to October. If you're looking for a more affordable trip, consider visiting in the shoulder seasons, like April or November.
What are the best Airbnb and vacation rentals in Oak Park, IL?
What are the best restaurants with local dishes in Oak Park, IL?
For a classic Oak Park experience, try Hemingway's Bistro. They've got great American comfort food, and it's a local favorite. If you're looking for something a little more upscale, try The Purple Pig in Chicago, just a short drive from Oak Park.
What are the most popular Airbnbs in Oak Park, IL?
What are the best walking or cycling routes in Oak Park, IL?
The Oak Park River Forest Trail is a great option for a leisurely bike ride or walk. It's a paved trail that runs for about 10 miles along the Des Plaines River. For a shorter walk, try the Oak Park Conservatory's gardens.
What are the best vacation rentals with a pool in Oak Park, IL?
Are there pet-friendly attractions in Oak Park, IL?
The Oak Park River Forest Trail is great for walking your dog, and there are plenty of dog parks in the area. You can also check out the Oak Park Farmers Market, which is pet-friendly.
What are the best rentals for families and kids in Oak Park, IL?
What are the benefits of choosing a vacation rental in Oak Park, IL?
Vacation rentals offer more space and privacy than a hotel, and they're often more affordable, especially for families or groups. You'll also have access to a kitchen, which is great for saving money on meals.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?
What are the top sports attractions and facilities in Oak Park, IL?
Oak Park is home to the Oak Park-River Forest High School, which has a great athletic program. You can also find several parks and recreation centers with sports fields and courts.
Destinations nearby
Choose the Right Vacation Rentals with a Terrace in Oak Park, IL
Enjoy stunning views from your private terrace when you book one of these vacation rentals in Oak Park, IL.
8.0 1 review
Oak Park, IL
07/17 – 07/27
$219/nighttotal: $2190 (10 )
Apartment ∙ 1 Bedroom ∙ 2 Guests
1 1
apartment , Forest Park
This Forest Park apartment rental is conveniently located near major highways, providing easy access to both Midway and O'Hare International Airports within a 30-minute drive. The one-bedroom, one-bathroom unit sleeps two guests and features a modern kitchen with a refrigerator and microwave, a terrace, and on-site parking.
9.8 152 reviews
Oak Park, IL
10/11 – 10/21
$346/nighttotal: $3460 (10 )
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 Mi From Wrigley!
2 2
apartment , Chicago
This charming bed and breakfast is located in Roscoe Village, a lively neighborhood just a short walk from Wrigley Field and the Brown Line. It's also close to restaurants, shops, and parks, making it a great base for exploring the city. The bed and breakfast has consistently received excellent ratings from guests. The spacious suite offers 1100 square feet of living space, comfortably accommodating up to 6 guests. It includes modern amenities like a full kitchen, a gas fireplace, a washer and dryer, and access to bike rentals for exploring the neighborhood.
9.7 297 reviews
Oak Park, IL
06/28 – 07/05
$483/nighttotal: $3381 (7 )
Cozy Downtown Mich Ave #7 | Gym+rooftop
2 5
apartment , Chicago
This penthouse apartment is located on Michigan Avenue, directly across from Grant Park and Lake Michigan, putting you in the heart of downtown Chicago's vibrant scene. The apartment enjoys excellent ratings for location, cleanliness, and user experience. The apartment offers 900 square feet of modern living space with two bedrooms and two bathrooms. Enjoy a fully equipped kitchen, a shared rooftop deck with city views, a fitness center, and easy access to public transportation and nearby attractions.
9.6 9 reviews
Oak Park, IL
06/28 – 07/05
$1325/nighttotal: $9275 (7 )
Stylish River North Suites: Luxury Living Near Chicagos Best Shopping&nightlife
2 5
apartment , Chicago
This Level River North two-bedroom apartment rental in Chicago's River North neighborhood offers easy access to the Magnificent Mile and the Loop, placing you minutes from iconic attractions like Millennium Park and Navy Pier. The 1,080-square-foot suite comfortably accommodates six guests and features two bathrooms, a fully equipped kitchen with a dishwasher, in-unit laundry, a balcony, and access to a swimming pool and sauna.
Best Oak Park, IL vacation rentals with air conditioning
9.9 34 reviews
Oak Park, IL
10/11 – 10/21
$274/nighttotal: $2740 (10 )
Walk To Dining & L Train • King Bed • Patio
1 2
apartment , Forest Park
This Forest Park rental offers a private backyard with a pergola and gas grill, ideal for enjoying the local climate, and is within walking distance of downtown Forest Park's dining, bars, and shops, with convenient Green and Blue Line 'L' train access to Chicago attractions. This WFH-ready home features two desks and high-speed Wi-Fi, an electric fireplace and Smart TVs in every room, and accommodates up to 6 guests with free driveway parking for one vehicle and family-friendly amenities like board games and books.
10 4 reviews
Oak Park, IL
06/25 – 07/25
$277/nighttotal: $8310 (30 )
3br Modern Apt • Gym • Workspace • Quiet Location
3 3
apartment , Dunning
This newly furnished 3-bedroom, 2-bathroom apartment is located in Dunning, a 15-minute drive from Chicago O'Hare International Airport and 25 minutes from Logan Square. This pet-friendly residence accommodates up to 9 guests and features a full kitchen with a dishwasher, central air conditioning, and a well-equipped gym with a Peloton bike, treadmill, and weights, plus a dedicated workspace with a dual-screen monitor.
9.6 30 reviews
Oak Park, IL
08/10 – 08/15
$275/nighttotal: $1375 (5 )
Downtown Oak Park/fast Wifi/free Parking/ Victorian Home/sleeps 6
2 2
apartment , Oak Park
This two-bedroom Oak Park apartment is located in downtown Oak Park, a two-minute walk from the Metra and "L" train stations, providing easy access to downtown Chicago, and is within walking distance of shops, restaurants, Target, Trader Joe's, and Frank Lloyd Wright homes. The 900-square-foot rental features two queen beds, a full-size sofabed, and a queen air mattress, accommodating up to six guests, and includes a kitchen with a fridge, microwave, and dishwasher, plus free garage parking, a terrace, a garden, and shared laundry facilities.
10 133 reviews
Oak Park, IL
08/10 – 08/15
$190/nighttotal: $950 (5 )
Cheerful Oak Park Apartment
1 2
apartment , Oak Park
This Oak Park apartment rental sits above a piano restoration shop, a five-minute walk from cafes, restaurants, and grocery stores, near the Frank Lloyd Wright Historic District and the Oak Park Conservatory. The one-bedroom unit sleeps two (with a third guest option for an extra fee), offering a king-size bed, Roku TV with Netflix, a private deck, and a fully equipped kitchen with complimentary coffee, tea, and snacks.