Best apartment offers in Oak Park, IL

247 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Oak Park, IL apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

247 Holiday apartments Oak Park, IL

Best family friendly Oak Park, IL Holiday Apartments and Self Catering Accommodations

Among the 247 accommodations in Oak Park, IL, here are the 4 best family friendly holiday apartments

Top Floor Of Historic Oak Park Home /2 Car Garage - Oak Park, IL
9.5 32 reviews
Oak Park, IL
14/10 – 17/10
348 €/nighttotal: 1044 € (3 )

Top Floor Of Historic Oak Park Home /2 Car Garage

3 4
apartment , Oak Park
This family-friendly flat is located in Oak Park, just under 2km from the Frank Lloyd Wright Historic District and Concordia University Chicago. The apartment is highly rated, with guests consistently praising its excellent facilities and comfortable atmosphere.
The 3-bedroom property offers 121 square metres of living space, comfortably accommodating up to 6 guests. The apartment features a fully equipped kitchen, free Wi-Fi, a washing machine, and access to a shared arcade/game room, providing plenty of entertainment options for families.
3 Bedroom Apartment, 15 Min Drive To Wrigley Field - Oak Park, IL
10 17 reviews
Oak Park, IL
28/06 – 05/07
306 €/nighttotal: 2142 € (7 )

3 Bedroom Apartment, 15 Min Drive To Wrigley Field

1 5
apartment , Chicago
This three-bedroom flat is situated near Lincoln Square and Albany Park, offering direct CTA Blue Line access to central Chicago, with Wrigley Field a 15-minute drive away.
This family-friendly apartment accommodates up to five guests and features a fully equipped kitchen, in-unit laundry, central air conditioning, and a comfortable living space with a 55-inch smart TV, all within easy reach of local dining and cultural attractions.
Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown - Oak Park, IL
10 1 review
Oak Park, IL
10/07 – 12/07
1558 €/nighttotal: 3116 € (2 )

Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown

5 14
apartment , Chicago
This spacious 223 square metre five-bedroom, three-bathroom residence in Chicago's Irving Park district offers a classic early-1900s Craftsman Foursquare design and is a 3.2 to 4 kilometre Uber journey from landmarks including Wrigley Field, the city centre, and Soldier Field.
This family-friendly apartment accommodates up to 14 guests and features a fully-equipped chef's kitchen, a dedicated games room with a pool table and 75" smart TV, high-speed Wi-Fi, air conditioning, and parking, with a check-out time of 10:00 AM.
Music-inspired 2br Garden Flat In Historic Uptown Near Legendary Music Venues - Oak Park, IL
10 4 reviews
Oak Park, IL
11/10 – 21/10
300 €/nighttotal: 3000 € (10 )

Music-inspired 2br Garden Flat In Historic Uptown Near Legendary Music Venues

2 2
apartment , Chicago
This renovated garden flat is located in Chicago's historic Uptown/Sheridan Park district, within a 1915 brownstone in a City of Chicago Landmark District, offering walking access to the Aragon Ballroom and Green Mill, and situated within 1.6 kilometres of Andersonville and the lakefront.
This 111 square metre apartment accommodates up to four guests, featuring two bedrooms, one bathroom with a Kohler rain shower, a chef-ready kitchen with LG appliances, in-unit laundry, and central air conditioning, all within an 8-minute walk of the CTA Red Line and a 10-minute walk to the Metra Ravenswood stop.

Best Oak Park, IL holiday apartments with a balcony

Cozy Downtown Mich Ave #7 | Gym+rooftop - Oak Park, IL
9.7 297 reviews
Oak Park, IL
28/06 – 05/07
418 €/nighttotal: 2926 € (7 )

Cozy Downtown Mich Ave #7 | Gym+rooftop

2 5
apartment , Chicago
This penthouse apartment is situated on Michigan Avenue, just a short walk from Grant Park and Lake Michigan, offering easy access to Chicago's vibrant attractions. The apartment boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The two-bedroom, two-bathroom apartment offers 84 square metres of living space, providing ample room for relaxation and comfort. The apartment comes equipped with a modern kitchen, a spacious living area, a terrace, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.
Secret Gallery On The Park - 2bd/1ba - Oak Park, IL
10 1 review
Oak Park, IL
28/06 – 05/07
382 €/nighttotal: 2674 € (7 )

Secret Gallery On The Park - 2bd/1ba

2 5
apartment , Chicago
This three-bedroom Chicago apartment, ideal for families or groups of up to eight, is located in the Gallery District, a short walk from Oak Street Beach and the 'L' train, offering easy access to the John Hancock Center and Willis Tower.
The two-level dwelling boasts two upgraded kitchens and bathrooms, a private patio, Roku access, complimentary Wi-Fi, and is within easy reach of shops and a grocery store.
1br Near O'hare  Balcony  Workspace - Oak Park, IL
Oak Park, IL
28/06 – 03/07
148 €/nighttotal: 740 € (5 )

1br Near O'hare Balcony Workspace

1 2
apartment , Chicago
This one-bedroom flat in Cook County offers convenient access to O'Hare Airport, major motorways, and Rosemont, placing it within reach of entertainment and shopping districts.
This 56 square metre flat, suitable for up to three guests, features a private balcony, a dedicated workspace, a fully equipped galley kitchen with dining for four, in-building laundry, and one allocated parking space for a pet-friendly stay.
Aurelien Spacious Apartments In The Heart Of Gold Coast - Oak Park, IL
9.7 537 reviews
Oak Park, IL
17/07 – 27/07
1092 €/nighttotal: 10920 € (10 )

Aurelien Spacious Apartments In The Heart Of Gold Coast

2 1
apartment , Chicago
This two-bedroom apartment is conveniently located in Chicago, just a short walk from Oak Street Beach and a mile from the city centre. It has received excellent ratings for location, cleanliness and user experience.
The apartment comes with a fully equipped kitchen, private bathroom and free Wi-Fi. You can also enjoy a range of amenities including a swimming pool, sauna, fitness centre and parking.

Frequently asked questions about apartment rentals in Oak Park, IL

Destinations nearby

Best Oak Park, IL holiday apartments with parking

Historic Oak Park Home - Oak Park, IL
9.6 5 reviews
Oak Park, IL
14/10 – 17/10
341 €/nighttotal: 1023 € (3 )

Historic Oak Park Home

3 4
apartment , Oak Park
This Oak Park flat, situated within the historic Samuel A. Rothermel Houses, is approximately 11.3 km from the United Centre and 14-16 km from Chicago landmarks including the Water Tower and Lincoln Park Zoo.
The 167-square-metre property boasts three bedrooms, one bathroom, sleeps six guests, and includes a fully equipped kitchen, air conditioning, a garden, and free Wi-Fi.
Theparadise/8mmidway20mdowntownquietarea.freewiffi - Oak Park, IL
9.6 282 reviews
Oak Park, IL
06/09 – 07/09
469 €/nightfor 1 night

Theparadise/8mmidway20mdowntownquietarea.freewiffi

1 2
apartment , Chicago
This Brighton Park flat, situated on a main road with a bus stop directly outside, offers easy access to Chicago's attractions.
Sleeping up to six guests, this ground-floor apartment boasts a fully equipped kitchen including a large fridge, oven, microwave and Keurig machine, plus a 50" Smart TV, free Wi-Fi, keyless entry, and an in-unit safety deposit box; optional garage parking is available at an extra cost.
Cozy Extended Stay: King Bed/fully Equipped/train - Oak Park, IL
10 3 reviews
Oak Park, IL
28/06 – 03/07
241 €/nighttotal: 1205 € (5 )

Cozy Extended Stay: King Bed/fully Equipped/train

1 2
apartment , Oak Park
This Oak Park flat is ideally situated for exploring local landmarks, with the Frank Lloyd Wright Historic District a 11-minute walk and the Ernest Hemingway Museum and House a 14-minute walk away.
This one-bedroom flat accommodates two guests and offers on-site parking, a fully equipped kitchen, and in-unit laundry, with excellent public transport links to Chicago's attractions.
Prime Location - Close To Public Transit, Little Italy, The Medical District And Uic By Allset Turnover - Oak Park, IL
9.2 187 reviews
Oak Park, IL
11/10 – 21/10
392 €/nighttotal: 3920 € (10 )

Prime Location - Close To Public Transit, Little Italy, The Medical District And Uic By Allset Turnover

2 2
apartment , Chicago
This two-bedroom flat is located in Chicago's West Loop, just a short distance from the Loop, Pilsen, Little Italy, the Medical District, and UIC. It has received excellent ratings for cleanliness and user experience, and a very good rating for its location.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It includes a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, parking, and internet access.

Best Oak Park, IL holiday apartments with air conditioning

Chic Retreat, 2 Queen Beds, Free Parking, Walk To Train - Oak Park, IL
10 2 reviews
Oak Park, IL
28/06 – 03/07
199 €/nighttotal: 995 € (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.
Stylish Luxe King Bed W/free Parkng Near Dt Oak Pk - Oak Park, IL
9.6 100 reviews
Oak Park, IL
14/10 – 17/10
223 €/nighttotal: 669 € (3 )

Stylish Luxe King Bed W/free Parkng Near Dt Oak Pk

2 4
apartment , Oak Park
This family-friendly apartment in Oak Park is situated just a short distance from the Frank Lloyd Wright Historic District, making it ideal for those interested in architecture.
The 111 square metre property features two bedrooms, a fully equipped kitchen, and can accommodate up to six guests, offering a comfortable and convenient base for exploring Oak Park and its surrounding attractions.
1br Apartment - Walk To Shops - Downtown Oak Park - Oak Park, IL
9.2 42 reviews
Oak Park, IL
11/10 – 21/10
202 €/nighttotal: 2020 € (10 )

1br Apartment - Walk To Shops - Downtown Oak Park

2 2
apartment , Oak Park
This one-bedroom flat in Oak Park offers a prime location in a district celebrated for its Frank Lloyd Wright architecture, placing guests within easy reach of local shops and restaurants, and just a 4-minute drive from the train station for access to Chicago.
This accommodation provides dedicated WiFi, two Smart TVs, and a fully equipped kitchen and bathroom, with a Pack 'n Play available for families, and is conveniently located a 2-minute drive from grocery stores and shopping centres, and a 20-minute drive to Downtown Chicago.
:: The Wolcott ::  Modern Elegance At Its Finest - Oak Park, IL
9.6 21 reviews
Oak Park, IL
10/07 – 12/07
3356 €/nighttotal: 6712 € (2 )

:: The Wolcott :: Modern Elegance At Its Finest

6 14
apartment , Chicago
This exquisite 6000 sq ft (557 sq m) single-family home is situated in Chicago's Wicker Park neighbourhood, offering easy access to the city's attractions.
The property boasts a spacious layout with four ensuite bedrooms and additional sleeping space for up to 16 guests, featuring a private 800 sq ft (74 sq m) garden, rooftop decks with Chicago skyline views, a jacuzzi, a fitness centre, and parking; other amenities include a wine cellar, pool table, and keyless entry.
©2026 cozycozy.com