Holiday Rentals in Oak Park, IL

This Dunning family home, situated approximately 9.7 kilometres from the Frank Lloyd Wright Historic District and Copernicus Centre, offers easy access to Milwaukee Avenue's amenities.
Sleeping six guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, private patio, free Wi-Fi, and parking; nearby attractions include the Fashion Outlets of Chicago.

This Near South Side Chicago flat is conveniently located a short walk from State Street and McCormick Place, and within 3.2km of Soldier Field and Lake Michigan.
The 60 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, and Smart TV.

This apartment is situated in historic Oak Park, just a short walk from the L train and 30 minutes from the Loop, MDW, and ORD, making it an ideal base for exploring the area. It has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The three-bedroom apartment offers 167 square metres of space, comfortably accommodating up to six guests. It boasts a fully equipped kitchen, air conditioning, parking, and a shared laundry facility, ensuring a convenient and comfortable stay.

This Oak Park holiday home, near the expressway offering a 24km commute to Chicago city centre and within walking distance of the Blue and Green Line stations, is ideally located for exploring this historic suburb.
This eight-bedroom, three-bathroom property boasts 270 square metres of living space across two apartments, sleeping up to twelve guests and featuring a fully fenced garden, parking, and a concierge service.

This charming house is located in Oak Park's Frank Lloyd Wright Historic District, just 1.4km from the Ernest Hemingway Museum and House, offering easy access to the area's architectural gems and vibrant atmosphere. The property has received excellent reviews from previous guests, highlighting its comfortable amenities and convenient location.
The house spans 167 square metres and comfortably accommodates up to 6 guests across its 3 bedrooms and 1 bathroom. Guests can enjoy a fully equipped kitchen, a dining area, a TV, and internet access, ensuring a comfortable and enjoyable stay.

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.

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.

This Elmwood Park apartment is located just 1.4 km from the Frank Lloyd Wright Historic District and 2.4 km from the Ernest Hemingway Museum and House, offering easy access to these popular attractions. The apartment consistently receives excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The flat has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private garden, and a terrace, providing everything you need for a relaxing and enjoyable stay.

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.

This comfortable apartment is situated in Avondale, a neighbourhood in Chicago, just a few kilometres from Lake Michigan. The area offers a relaxed atmosphere, with easy access to local restaurants and shops. Guests consistently rate this apartment as excellent.
The apartment has three bedrooms and one bathroom, offering enough space for up to five guests. The apartment also comes with a range of amenities, including a kitchen with a fridge, microwave oven, and dishwasher, as well as a garden, terrace, and parking.

This newly renovated dual-suite apartment is located in Chicago's Chinatown, just a short walk from public transport and a 5-kilometre drive from downtown and other attractions like Millennium Park. The apartment has received excellent ratings for location, cleanliness, and user experience.
The apartment has two separate living spaces, each with its own kitchen, dining room, and living room, making it ideal for larger groups. Each suite is fully equipped with modern appliances, including a fridge, freezer, microwave, dishwasher, and air conditioning, along with a terrace, garden, and spa.

This four-bedroom corporate apartment in Chicago's Near North Side offers prime access to Old Town, Lincoln Park, and the Clybourn Corridor, situated just 500 meters from New City shopping plaza and a short walk from the Second City Theater, with the North Branch Trail leading to the lakefront and multiple public transport options including the Red Line train for direct routes downtown.
The 112 square meter dwelling accommodates up to ten guests with four bedrooms, including two en-suite suites, a fully equipped kitchen featuring stainless steel appliances, and in-unit laundry, all complemented by spectacular city views and high-speed internet.

This charming coach house is situated in historic Forest Park, just 8 miles west of downtown Chicago, offering a convenient location close to the Blue Line train and I-290. The apartment has received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers.
The self-catering property offers one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, complimentary refreshments, and the option to borrow bicycles or kayaks.

This charming studio apartment is situated in Oak Park's Arts District, just a short walk from the Frank Lloyd Wright Home and Studio, and a mere 400 feet from the CTA Blue Line, making it easy to explore both Oak Park and downtown Chicago. The studio consistently receives excellent ratings for its location, cleanliness, and overall experience.
This comfortable apartment offers two bedrooms and one bathroom across 86 square metres. Guests can enjoy a fully equipped kitchen, a private garden, a spa, and parking, as well as keyless access and a patio with a grill for warm weather enjoyment.

This Oak Park flat offers a tranquil base, located just 24 kilometres from downtown Chicago and close to local attractions.
This spacious four-bedroom residence accommodates up to eight guests and features a fully equipped kitchen, air conditioning, a garden, on-site parking, and an arcade for entertainment.

This Chicago basement flat, sleeping four, is situated in a four-unit building; precise location within the city is unspecified.
The renovated (2021) self-catering property boasts a Roku TV, shared laundry, a private backyard with fire pit and seasonal above-ground pool, and accommodates up to four guests for a pet-friendly stay (a £24 pet fee applies).