This newly remodelled private, top-floor flat in Irving Park, Chicago, offers an authentic city living experience within a traditional two-flat building, providing a peaceful and central base for exploring the city's attractions. This 2-bedroom, 1-bathroom apartment accommodates up to 4 guests, featuring air conditioning and a kitchen, with exclusive use of the entire top-floor unit and backyard, ensuring modern comfort within a character-filled building.
9.5 55 reviews
Oak Park, IL
17/07 – 27/07
A$317/nighttotal: A$3170 (10 )
1 Bedroom Apartment In Lovely Victorian House
1 1
apartment , Oak Park
This apartment is conveniently located in Oak Park, just 2km from the train station, offering a quick 20-minute commute to Chicago, and is situated in a peaceful, family-friendly neighbourhood. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment is ideal for couples, with one bathroom and a well-equipped kitchen. You can enjoy amenities such as Wi-Fi, air conditioning, and a fridge, freezer, and microwave.
9.7 387 reviews
Oak Park, IL
28/06 – 03/07
A$276/nighttotal: A$1380 (5 )
Small But Mighty 700 Sqft Cottage Apt (1br/1ba)
1 2
apartment , Oak Park
This ground floor flat is located in Oak Park, just 1 kilometre from the Blue Line Station and a 2-kilometre drive to downtown Chicago. It has consistently received excellent ratings for location, cleanliness and user experience. The flat has one bathroom and can comfortably accommodate up to 4 guests. It comes equipped with a fully fitted kitchen, high-speed internet, a washing machine and dryer, and a private garage.
9.9 59 reviews
Oak Park, IL
17/07 – 27/07
A$316/nighttotal: A$3160 (10 )
Restored Mid-century 4 Square
1 1
apartment , Oak Park
This Oak Park apartment, situated in a central location offering easy access to Chicago's attractions (though precise distances aren't provided), is ideal for exploring both Oak Park and the city. The first-floor, four-room flat features a king-size bedroom, sofa bed, private parking, a three-season porch, and accommodates up to four guests, boasting a fully equipped kitchen including a dishwasher.
10 80 reviews
Oak Park, IL
10/07 – 12/07
A$2713/nighttotal: A$5426 (2 )
Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar
1 14
apartment , Chicago
This apartment is located on a peaceful, tree-lined street in a neighbourhood just a few kilometres from Chicago's city centre, offering easy access to major highways and public transportation. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience. This spacious property can comfortably accommodate up to 16 guests and features a unique speakeasy-style basement with a full bar, game room and retro popcorn machine. The apartment also boasts a fully equipped kitchen, multiple king and queen beds, a dedicated workspace, a spacious back deck with a fire table and a free covered garage and street parking.
9.8 39 reviews
Oak Park, IL
11/10 – 21/10
A$271/nighttotal: A$2710 (10 )
Darling Flat Walk To Op
1 2
apartment , Oak Park
This newly refurbished one-bedroom flat in Oak Park is situated within a few hundred metres of Oak Park's downtown area and the Green Line station, offering easy access to Chicago. The 1-bathroom apartment, sleeping up to two guests, includes a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, parking, internet access, and is close to Frank Lloyd Wright's architectural masterpieces.
9.8 36 reviews
Oak Park, IL
11/10 – 21/10
A$321/nighttotal: A$3210 (10 )
A Quiet Stay While You Are Away
2 2
apartment , Oak Park
This apartment is in the Frank Lloyd Wright historic district, a short walk from Unity Temple and the town centre. It has excellent user ratings and is popular with families. The home has two bedrooms and can comfortably sleep four people. Guests can enjoy a garden, a terrace, a fully-equipped kitchen and parking.
Oak Park, IL
11/10 – 21/10
A$646/nighttotal: A$6460 (10 )
The King's Corner / Ground Level / Train Access
1 2
apartment , Oak Park
This Oak Park flat is ideally situated for exploring the area's architectural heritage, with the Frank Lloyd Wright Historic District 880 metres away and the Ernest Hemingway Museum and House 1.1 kilometres distant. This one-bedroom flat accommodates two guests and includes a kitchenette with a fridge and microwave, air conditioning, and on-site parking, with shared laundry facilities available.
9.8 67 reviews
Oak Park, IL
11/10 – 21/10
A$618/nighttotal: A$6180 (10 )
Oak Park Home With Grill - 5 Mi To Garfield Park!
3 2
house , Oak Park
This charming Oak Park house is situated just 14 kilometres from the United Center, 16 kilometres from Lincoln Park Zoo, and 18 kilometres from Union Station, offering easy access to Chicago's attractions. It is located in a quiet neighbourhood within the historic village of Oak Park, known for its beautiful architecture and vibrant arts scene. The house has received excellent ratings for cleanliness, location, and user experience. The property has three bedrooms and one bathroom, spanning 167 square metres and comfortably accommodating up to six guests. Enjoy amenities such as a fully equipped kitchen, free Wi-Fi, a private fire pit, and a peaceful setting, perfect for a relaxing getaway.
9.9 132 reviews
Oak Park, IL
25/06 – 25/07
A$373/nighttotal: A$11190 (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.
9.3 3 reviews
Oak Park, IL
28/06 – 03/07
A$367/nighttotal: A$1835 (5 )
Wonderful 1br Retreat With Balcony In Oak Park
1 2
apartment , Oak Park
This Oak Park flat offers a stylish base for four guests, situated within a short walk of the Frank Lloyd Wright Home and Studio and easily accessible to the Ernest Hemingway Museum and downtown amenities, with convenient public transport links for exploring Chicago. This two-bedroom, two-bathroom apartment features air conditioning, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, and access to a garden and fitness centre, making it ideal for group travel and experiencing Oak Park's unique culture.
Oak Park, IL
28/06 – 03/07
A$287/nighttotal: A$1435 (5 )
Free Parking+20 Min To Downtown Chicago
2 2
apartment , Oak Park
This two-bedroom, two-bathroom flat in Oak Park offers excellent access to the Frank Lloyd Wright Historic District, a mere 5-minute walk away, and is conveniently situated 400 metres from Ridgeland metro station for straightforward travel to Chicago's Millennium Park (14-minute drive) and Grant Park (15-minute drive). This accommodation for up to six guests provides Wi-Fi, air conditioning, and essential amenities, with easy access to public transport and attractions such as the United Centre (10-minute drive) and Michigan Avenue.
Best family friendly Oak Park, IL holiday rentals
Among the 269 accommodations in Oak Park, IL, here are the 4 best family friendly rentals
9.9 158 reviews
Oak Park, IL
10/07 – 12/07
A$2667/nighttotal: A$5334 (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.
9.9 170 reviews
Oak Park, IL
11/10 – 21/10
A$416/nighttotal: A$4160 (10 )
Historic Coach House In Evanston One Block To Beach And Close To Town And Nu!
1 2
apartment , Evanston
This historic manor house is situated in Evanston's Lakeshore Historic District, just 0.8 kilometres from Lake Michigan's beaches and a short walk from downtown Evanston and Northwestern University. The property has received excellent ratings for its location, cleanliness, and overall user experience. The house has one bedroom and one bathroom spread over 84 square metres, comfortably accommodating up to three guests. The property offers a range of amenities, including a fully equipped kitchen, a private garden, a spa, parking, and complimentary bicycles and beach passes for exploring the area and enjoying the lake.
9.9 375 reviews
Oak Park, IL
11/10 – 21/10
A$415/nighttotal: A$4150 (10 )
Family-friendly, Stylish Chicago Apartment In Logan Square
1 2
apartment , Chicago
This charming Chicago flat is situated in Logan Square, a popular neighbourhood known for its trendy restaurants, bars, and art galleries, and is within easy reach of the 606 Bloomingdale Trail and the Logan Square Farmers Market. The apartment has received excellent ratings for its location, cleanliness, and overall experience. This three-bedroom home offers 111 square metres of space and can comfortably accommodate up to seven guests. It comes equipped with a well-stocked kitchen, a private garden, laundry facilities, and a range of amenities for families, including a baby-friendly pack-and-play and toys.
9.8 10 reviews
Oak Park, IL
17/07 – 27/07
A$421/nighttotal: A$4210 (10 )
Chic & Cozy Near Ord>mdw>dt>hosp
2 1
apartment , Berwyn
This Berwyn apartment is situated 4.3km from the Frank Lloyd Wright Home and Studio, offering easy access to Loyola University Medical Centre and Concordia University Chicago (both within 9.6km). The two-bedroom, one-bathroom flat sleeps four, boasting a fully equipped kitchen, in-unit laundry, free Wi-Fi, a Smart TV, and parking, making it ideal for families visiting the area.
Best Oak Park, IL holiday rentals with parking
8.9 215 reviews
Oak Park, IL
28/06 – 05/07
A$520/nighttotal: A$3640 (7 )
Family Friendly 2br South Loop Suite With Optional Parking And Gym Access Sleeps Up To 8 Near Mccormick Place And Soldier Field
3 5
apartment , Chicago
This modern apartment is located in Chicago's McCormick Place district, just a short distance from the Field Museum of Natural History and the Art Institute of Chicago. The property has received excellent ratings for location, cleanliness, and overall user experience. The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, a fitness centre, a terrace, and on-site parking, making it perfect for families or groups of friends exploring the city.
9.2 5 reviews
Oak Park, IL
25/06 – 25/07
A$477/nighttotal: A$14310 (30 )
A Charming Modern Chic Basement Apartment
1 3
apartment , Chicago
This Chicago basement flat is located approximately 5.6km from Loyola University Chicago, 10.3km from Wrigley Field, and 17.7km from downtown attractions including the United Centre and the Museum of Contemporary Art. The 46 square metre self-contained apartment features one bedroom, one bathroom, sleeps up to 11 guests, and includes free Wi-Fi, air conditioning, parking, and all linen.
10 1 review
Oak Park, IL
28/06 – 05/07
A$468/nighttotal: A$3276 (7 )
South Loop 2br Chicago 420-friendly Near Mccormick & Chinatown
2 5
apartment , Chicago
This South Loop flat is situated 2.6 kilometres from the Field Museum of Natural History and 2.7 kilometres from DePaul University, offering convenient access to McCormick Place and Chinatown. This family-friendly apartment accommodates up to 11 guests, featuring air conditioning, a private terrace, a fully equipped kitchen, and on-site parking, with complimentary WiFi provided throughout.
Oak Park, IL
25/06 – 25/07
A$263/nighttotal: A$7890 (30 )
74 M² House ∙ 2 Bedrooms ∙ 4 Guests
2 3
house , Forest Park
House for up to 4 people. You will be based in Forest Park. Facilities and services: a kitchen, a freeze and a garden. Take advantage of the Free Parking with this accommodation in Forest Park!
Frequently asked questions about holiday rentals in Oak Park, IL
What are the top family-friendly attractions in Oak Park, IL?
Oak Park has plenty for families! The Oak Park Conservatory is a great place to visit, with its beautiful gardens and educational exhibits. The Oak Park River Forest Museum is also a popular choice, with interactive exhibits that are fun for all ages. And don't forget the Oak Park Farmers Market, which is held every Saturday from May to October.
What are the best Airbnb and holiday rentals 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 in the spring or autumn. The weather is mild, and the crowds are smaller. You'll be able to enjoy all that Oak Park has to offer without the summer heat or the winter chill.
What are the most popular Airbnbs in Oak Park, IL?
What are the best restaurants with local dishes in Oak Park, IL?
Oak Park has a fantastic food scene. For a taste of local cuisine, try The Purple Pig for its creative dishes and The Map Room for its classic American fare. And don't forget to grab a slice of pizza at Pizzeria Bebu, a local favourite.
What are the best holiday rentals with a pool in Oak Park, IL?
What are the best walking or cycling routes in Oak Park, IL?
Oak Park has a great network of walking and cycling trails. The Forest Trails are a popular choice for a scenic stroll or bike ride. You can also explore the Oak Park River Forest Trail, which winds its way through the village and offers beautiful views of the Des Plaines River.
What are the best rentals for families and kids in Oak Park, IL?
Are there pet-friendly attractions in Oak Park, IL?
Oak Park is a very dog-friendly town! Many of the parks and restaurants welcome furry friends. The Oak Park Conservatory has a designated dog-walking area, and the Forest Trails are perfect for a leisurely stroll with your pup.
What are the best rentals or Airbnbs with a jacuzzi in Oak Park, IL?
What are the benefits of choosing a vacation rental in Oak Park, IL?
Choosing a vacation rental in Oak Park can be a great option for families or groups who want more space and privacy than a hotel room. You'll also have access to a kitchen, so you can save money by cooking your own meals. And many vacation rentals are located in quiet neighbourhoods, offering a more peaceful experience than a hotel in the heart of the city.
Destinations nearby
Best Oak Park, IL holiday rentals with a balcony
8.5 2 reviews
Oak Park, IL
17/07 – 27/07
A$1415/nighttotal: A$14150 (10 )
New! Spacious Art Deco Modern 5 Bd/3ba Condo
5 1
apartment , Chicago
This spacious Chicago apartment, located near the United Center, Water Tower Place, and Union Station (all within a 3-5 km radius), offers easy access to major attractions. The 279 square metre property boasts a five-bedroom, three-bathroom layout sleeping up to 27 guests, complete with a fully equipped kitchen, free Wi-Fi, private parking, and a terrace.
Oak Park, IL
28/06 – 05/07
A$516/nighttotal: A$3612 (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.
9.8 309 reviews
Oak Park, IL
28/06 – 03/07
A$1390/nighttotal: A$6950 (5 )
Lincoln Park Single Family Home (4bdrm 3.5 Bth)-2 Car Garage 4200sqft Sleeps 24
4 2
apartment , Chicago
This spacious house in Lincoln Park is ideally located just 15 blocks from Wrigley Field, 5 blocks from the Kennedy Expressway, and 6 blocks from the EL, making it easy to explore the city. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience. This four-bedroom home spans 390 square metres and comfortably accommodates up to 24 guests. The house offers a range of amenities, including a private garage, a fully equipped kitchen, a jacuzzi, a terrace, a garden, and a spa, ensuring a relaxing and enjoyable stay.
10 2 reviews
Oak Park, IL
06/09 – 07/09
A$1140/nightfor 1 night
Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife
1 2
apartment , Chicago
This Level River North apartment, a stylish flat in Chicago's River North district, is minutes from the Magnificent Mile and across the river from the Loop. The 56 square metre (602 square foot) studio suite sleeps four, offering a fully equipped kitchen, in-suite laundry, complimentary Wi-Fi, and access to a swimming pool, sauna, and parking; nearby attractions include the Chicago Theatre and Art Institute of Chicago.
Best Oak Park, IL holiday rentals with air conditioning
9.9 49 reviews
Oak Park, IL
28/06 – 05/07
A$333/nighttotal: A$2331 (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.
Oak Park, IL
25/06 – 25/07
A$187/nighttotal: A$5610 (30 )
Great Area Logan Square Apt Games Pets - Sleeps 5
1 3
apartment , Chicago
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.
10 2 reviews
Oak Park, IL
28/06 – 03/07
A$327/nighttotal: A$1635 (5 )
Chic Retreat, 2 Queen Beds, Free Parking, Walk To Train
1 2
apartment , Oak Park
This Oak Park flat is situated 0.8km from the Frank Lloyd Wright Historic District and 2.6km from Concordia University Chicago, offering convenient access to public transport. The one-bedroom apartment, sleeping two guests, includes a fully equipped kitchen, in-unit laundry, parking, and a terrace; explore nearby attractions such as the Walt Disney House and Loyola University Medical Centre, both within 9.6km.
9.8 42 reviews
Oak Park, IL
11/10 – 21/10
A$288/nighttotal: A$2880 (10 )
Explore Oak Park & Chicago
1 2
apartment , Oak Park
This Oak Park flat is situated a two-minute walk from the Metra station, offering easy access to Chicago's city centre and is within walking distance of Oak Park's downtown area, including the Frank Lloyd Wright sites and Hemingway Museum. The two-bedroom, one-bathroom apartment sleeps three guests and includes a fridge, microwave, air conditioning, and internet access; nearby attractions include the Oak Park Festival Theatre and St Edmund's Parish.