This private top-floor flat is situated in Chicago's Avondale/Logan Square district, approximately 12.8 to 16 kilometres from downtown landmarks such as the Merchandise Mart and Cloud Gate. This 58-square-metre accommodation allows pets, offers high-speed internet, air conditioning, parking, and features a PacMan arcade machine and wall-sized Connect 4 for entertainment, with a capacity for five guests.
9.6 55 reviews
Oak Park
06/28 – 07/03
HK$1427/nightTotal: HK$7135 (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.
9.8 18 reviews
Oak Park
09/06 – 09/07
HK$5338/nightfor 1 night
Chic 3bed 2bath Home With Free Parking Close To United Center
3 2
apartment , Oak Park
This family-friendly Oak Park house, situated within 5km of both the Frank Lloyd Wright Historic District and Concordia University Chicago, offers convenient access to local attractions and public transport. The 139 square metre property boasts three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private garden, parking, and free Wi-Fi.
10 16 reviews
Oak Park
06/28 – 07/05
HK$2437/nightTotal: HK$17059 (7 )
New Boho 3br | King Bed, Firepit/close To Downtown
1 5
apartment , Chicago
This three-bedroom apartment is located in the Kilbourn Park/Logan Square neighbourhood of Chicago, approximately 16km from Millennium Park and 12km from Wrigley Field, offering easy access to the Blue Line for travel to the city centre and O'Hare International Airport. The 3-bedroom property sleeps up to 8 guests, features a king-size bed, two double beds and a fold-away single bed, a fully equipped kitchen, private garden with fire pit, high-speed Wi-Fi, and free on-street parking; baby amenities and EV charging are also available.
9.6 10 reviews
Oak Park
06/28 – 07/05
HK$1613/nightTotal: HK$11291 (7 )
Chicago Boutique Hideaway • Private Deck, Fire Pit
1 5
apartment , Chicago
This Chicago flat, located in a quiet district, offers convenient access to various dining and coffee establishments, Sister Lavender Spa (274 metres away), REPS Fitness & The Garage gym (366 metres away), and park trails for running and biking (457 metres away). This private, tranquil retreat accommodates up to six guests, featuring a fully stocked kitchen, in-unit washer and dryer, keyless entry, and a private outdoor deck with a fire pit, ensuring a comfortable stay.
9.9 49 reviews
Oak Park
06/28 – 07/05
HK$1833/nightTotal: HK$12831 (7 )
Karlov Inn | Stylish Chicago 2br Retreat
2 5
apartment , Chicago
This Humboldt Park flat is conveniently located near the 606 Trail and CTA buses, offering easy access to downtown Chicago, approximately a few kilometres away. The two-bedroom, one-bathroom apartment sleeps five guests, features a well-equipped kitchen, a dedicated workspace with high-speed Wi-Fi, and a garden, plus a jacuzzi and parking.
10 6 reviews
Oak Park
06/28 – 07/05
HK$2351/nightTotal: HK$16457 (7 )
Charming Oak Park Retreat
1 5
apartment , Oak Park
This Oak Park flat is ideally situated near public transport links, offering easy access to Chicago's city centre and within walking distance of Oak Park's Frank Lloyd Wright Historic District. The two-bedroom, one-bathroom apartment sleeps six, features free Wi-Fi, a dedicated workspace, on-site parking, a fully equipped kitchen and a smart TV, perfect for families or groups exploring the area.
9.5 264 reviews
Oak Park
06/28 – 07/03
HK$1559/nightTotal: HK$7795 (5 )
Cozy Modern Unit W/ Easy Access To Downtown Chi
2 2
apartment , Oak Park
This two-bedroom flat is located in Oak Park, just 1.9 kilometres from the Frank Lloyd Wright Historic District and 3.5 kilometres from Concordia University Chicago, offering a peaceful retreat close to local attractions. The property has received excellent ratings for location, cleanliness, and overall user experience. The flat comfortably accommodates up to five guests and features a well-equipped kitchen, a private garden, a terrace, and free Wi-Fi. Guests can enjoy easy access to public transport, with Oak Park Station just an 8-minute walk away, making exploring Oak Park and Chicago a breeze.
10 609 reviews
Oak Park
09/06 – 09/07
HK$8628/nightfor 1 night
Modern Victorian With Old World Charm
1 2
apartment , Oak Park
This charming flat is located in Oak Park's historic district, just a short walk from public transport, restaurants, shops and grocery stores. It has received excellent ratings for its location, cleanliness and overall experience. The two-bedroom, two-bathroom apartment is situated on the second floor and has a private balcony. Guests can enjoy a fully equipped kitchen, free parking, access to a shared laundry facility, and a range of amenities, including shampoo, conditioner, body wash, hair dryers and fresh towels.
9.0 1120 reviews
Oak Park
07/10 – 07/12
HK$18133/nightTotal: HK$36266 (2 )
The Hotel & Athletic Club At Midtown
4 14
resort , Chicago
The Hotel & Athletic Club at Midtown is conveniently located in Chicago's Midtown neighbourhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The hotel consistently receives high ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. The hotel offers a range of comfortable and modern rooms, each equipped with amenities such as air conditioning, flat-screen TVs, and private bathrooms. Guests have access to a wide array of facilities including indoor and outdoor swimming pools, a spa, a fitness centre, tennis courts, and a variety of fitness classes, making it a great choice for those seeking a wellness-focused getaway.
10 9 reviews
Oak Park
06/25 – 07/25
HK$2068/nightTotal: HK$62040 (30 )
O'hare,2 Bedq K/washerd/parking.
1 3
apartment , Franklin Park
This Franklin Park apartment, ideally located near public transport, restaurants, and parks, offers easy access to local amenities. The two-bedroom, one-bathroom flat sleeps four guests comfortably, boasting a king and queen bed, plus sofas, a dedicated office, in-unit laundry, parking, and high-speed internet with Netflix.
9.9 132 reviews
Oak Park
06/25 – 07/25
HK$2053/nightTotal: HK$61590 (30 )
Beautiful (No Chores No Cleaning Fees)
1 3
apartment , Chicago
This stylish two-bedroom Chicago apartment, near Humboldt Park, offers easy access to the park's amenities. The 50-inch TV, Netflix, Prime Video, in-unit laundry, and private patio with grill, accommodate four guests comfortably in this well-equipped flat.
Best family friendly Oak Park holiday rentals
Among the 269 accommodations in Oak Park, here are the 4 best family friendly rentals
This charming Victorian home is located in Oak Park, just 8 kilometres from downtown Chicago, offering easy access to parks, the Oak Park Conservatory and a pool/water park. The property consistently receives excellent ratings for location, cleanliness and user experience. This three-bedroom property comfortably accommodates up to seven guests. Enjoy a blend of vintage and contemporary design with modern conveniences including a fully equipped kitchen, Wi-Fi speakers and a spacious garden with a patio, fire pit and Weber gas grill.
This apartment is situated in the trendy Pilsen neighbourhood, just 10 kilometres from the city centre and close to Chinatown, offering easy access to Chicago's attractions. The property boasts excellent user, location and cleanliness ratings. This spacious flat has four bedrooms and two bathrooms, comfortably accommodating up to 16 guests. The apartment is fully equipped with a kitchen, air conditioning, free street parking, and high-speed Wi-Fi, ensuring a comfortable and convenient stay.
8.8 5 reviews
Oak Park
06/28 – 07/05
HK$2616/nightTotal: HK$18312 (7 )
Great Location. 5min To Mccormick Place. Downtown. Chinatown
3 5
apartment , Chicago
This Bridgeport, Chicago flat is situated near Chinatown, approximately 0.8 km from McCormick Place and the city centre, offering easy access to Guaranteed Rate Field. The three-bedroom property sleeps eight, includes a full kitchen with dishwasher, in-unit laundry, and a private backyard with cornhole and barbecue facilities; long-term stays are welcome.
8.2 35 reviews
Oak Park
09/06 – 09/07
HK$2309/nightfor 1 night
Bright Garden Studio
1 2
studio , Evanston
This Evanston studio apartment, located in a quiet, family-friendly upper-middle-class neighbourhood with easy access to CTA bus and train lines for travel to Chicago attractions, offers a convenient base for exploring the city. The 74-square-metre (approximately 796 square feet) self-catering apartment features a sophisticated open-plan design, accommodating up to four guests and boasting amenities including a Jacuzzi, garden, and parking.
Best Oak Park holiday rentals with parking
9.8 139 reviews
Oak Park
10/11 – 10/21
HK$1576/nightTotal: HK$15760 (10 )
Cheerful Remodel Prime Location
1 2
apartment , Oak Park
This Oak Park flat is situated a short distance from the Green Line, offering easy access to Chicago city centre and is within 0.8 km of Whole Foods and Trader Joe's. The one-bedroom, one-bathroom apartment sleeps two guests and includes parking, Wi-Fi, air conditioning, and a fully equipped kitchen; nearby attractions include Oak Park's shops and restaurants, easily accessible within a 0.8 km walk.
8.2 5 reviews
Oak Park
06/25 – 07/25
HK$2765/nightTotal: HK$82950 (30 )
Exquisite Rogers Park 1 Bedroom, 1 Bath Apartment Near Evanston
1 3
apartment , Chicago
This Rogers Park flat in Chicago is situated 3.5km from Loyola University Chicago and within a reasonable driving distance of Wrigley Field and Lincoln Park Zoo. The 93 square metre self-catering apartment sleeps two, offering a fully equipped kitchen, free Wi-Fi, private parking, and a private entrance.
Oak Park
09/06 – 09/07
HK$7729/nightfor 1 night
Comfortable Living, Within Reach!
2 2
apartment , Oak Park
This Oak Park flat is located 8.5 kilometres from the United Centre, providing easy access to downtown Chicago landmarks within an 8.5-kilometre radius and is 9.9 kilometres from Midway International Airport. This one-bedroom flat offers accommodation for up to 11 guests, featuring air conditioning, complimentary Wi-Fi, a fully equipped kitchen with a dishwasher and oven, and an in-unit washing machine, with parking available and pets permitted.
9.6 676 reviews
Oak Park
09/06 – 09/07
HK$10144/nightfor 1 night
Designer Themed 4 Bedroom In Best Location With Patio And Fireplace
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.
Frequently asked questions about holiday rentals in Oak Park
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 Home and Studio. It's a must-see for architecture enthusiasts and gives you a glimpse into the life of this famous architect. You should also visit the Oak Park River Forest Museum, which tells the story of the area's history and culture.
What are the best Airbnb and vacation rentals in Oak Park?
Which neighborhood in Oak Park, IL should you consider for a vacation rental?
The heart of Oak Park is the village centre, and it's a great place to stay. It's walkable to many restaurants, shops, and attractions, including the Oak Park Public Library. If you prefer a quieter neighbourhood, consider the area around the Forest Park station, which has a more residential feel.
What are the top family-friendly attractions in Oak Park, IL?
The Oak Park Conservatory is a great spot for families, with its beautiful gardens and interactive exhibits. The park also has a playground and a splash pad. The Scoville Park is another great option, with its large green space, playground, and tennis courts.
What are the best vacation rentals with a pool in Oak Park?
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 during the shoulder seasons, which are spring and autumn. The weather is pleasant, and the crowds are smaller. You'll find good deals on accommodation during these periods.
What are the best rentals for families and kids in Oak Park?
What are the best budget-friendly activities in Oak Park, IL?
Oak Park has many free or low-cost activities, such as visiting the Oak Park Public Library, taking a walk or cycle along the Des Plaines River Trail, or enjoying a picnic in one of the many parks. The village also has a number of free concerts and events throughout the year.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park?
What are the best restaurants with local dishes in Oak Park, IL?
Oak Park has a vibrant culinary scene, with many restaurants serving local and regional dishes. Some of the best include Maya Del Sol, which serves Mexican cuisine, and the Oak Park Brewing Company, which serves craft beers and pub fare.
What are the best walking or cycling routes in Oak Park, IL?
Oak Park has a network of walking and cycling paths, including the Des Plaines River Trail, which runs along the river for over 100 km. The village also has a number of parks and green spaces, which are great for a leisurely stroll or bike ride.
Are there pet-friendly attractions in Oak Park, IL?
Many of Oak Park's parks and green spaces are pet-friendly, including Scoville Park and the Oak Park Conservatory. You can also find dog-friendly restaurants and cafes in the village.
What are the benefits of choosing a vacation rental in Oak Park, IL?
Vacation rentals in Oak Park offer more space and privacy than hotels, and they are often located in more residential areas. They can also be a more affordable option, especially for families or groups.
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 has a number of athletic facilities, including a football stadium, a baseball field, and a swimming pool. The village also has a number of parks and green spaces with tennis courts, basketball courts, and playgrounds.
Destinations nearby
Best Oak Park holiday rentals with a balcony
10 162 reviews
Oak Park
10/11 – 10/21
HK$13722/nightTotal: HK$137220 (10 )
Fantastic Home In Wicker Park
5 2
apartment , Chicago
This five-bedroom apartment is conveniently located in Wicker Park, just a short walk from the trendy shops, bars, and restaurants of this popular Chicago neighbourhood. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travellers. The spacious home has three living areas, a dedicated dining space, and 12 beds, making it ideal for large groups or families. The apartment offers modern amenities, including a fully equipped kitchen, washer and dryer, secure parking, a terrace, and a garden, ensuring a comfortable and enjoyable stay.
9.6 383 reviews
Oak Park
06/28 – 07/05
HK$14235/nightTotal: HK$99645 (7 )
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
4 5
apartment , Chicago
This apartment is located in Wrigleyville, just steps away from Wrigley Field, a lively area with a bustling atmosphere. It has excellent user, location and cleanliness ratings. The flat accommodates up to 9 guests in four bedrooms, ideal for families or groups. It offers a fully equipped kitchen, two bathrooms, a terrace, a garden, and a fireplace, plus a washer and dryer, Smart TVs, and a Keurig coffee maker.
Oak Park
10/11 – 10/21
HK$3199/nightTotal: HK$31990 (10 )
Elegant Retreat In Historic Oak Park
2 2
apartment , Oak Park
This recently refurbished two-bedroom, two-bathroom flat is situated in Oak Park, providing convenient access to local shops, cafes, and parks, with public transport links to Chicago. Spanning 93 square meters, this accommodation for four includes a fully equipped kitchen, air conditioning, a terrace, spa, and parking, with paid laundry facilities available in the building and nearby opportunities for swimming, cycling, and hiking.
This two-bedroom flat is situated in the Norwood Park/Edison Park neighbourhood of Chicago, a quiet area located 12 kilometres from Loyola University Chicago and 15 kilometres from Wrigley Field. The 85 square metre property can accommodate up to four guests and features a fully equipped kitchen, a patio, a garden, and outdoor play equipment, ideal for families with children.
Best Oak Park holiday rentals with air conditioning
Oak Park
07/17 – 07/27
HK$1627/nightTotal: HK$16270 (10 )
The Urban Oasis
1 1
apartment , Chicago (IL)
Apartment rental. You will be in Chicago (IL). Services and facilities include a dish washer, a fridge and an iron. Take advantage of the air conditioning in this apartment!
9.8 135 reviews
Oak Park
07/10 – 07/12
HK$15478/nightTotal: HK$30956 (2 )
7b 3ba Private Unit In Lincoln Park Near Wrigley
7 14
apartment , Chicago
This seven-bedroom, three-bathroom Lincoln Park duplex in Chicago offers convenient access to Lincoln Park itself and Chicago's attractions, though precise distances aren't specified. Sleeping fourteen guests, this spacious two-storey property features a fully equipped kitchen with outdoor grill, fast Wi-Fi, and free overnight street parking for two cars; additional paid parking is available nearby.
9.9 227 reviews
Oak Park
06/28 – 07/05
HK$2115/nightTotal: HK$14805 (7 )
The Evergreen House
1 5
apartment , Chicago
This first-floor flat is located in a quiet residential area of Chicago, just a short distance from the city centre and within easy reach of public transport. The apartment has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience. The flat is ideal for families or groups of up to 5 people, with two bedrooms and one bathroom. It comes with a well-equipped kitchen, multiple TVs with access to Netflix, free street parking, a private backyard and a washer and dryer in the basement.
9.5 4 reviews
Oak Park
07/10 – 07/12
HK$24270/nightTotal: HK$48540 (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.