Villas and Holiday homes in Chicago, IL

This Chicago residence is situated in East Garfield Park, offering a 4-minute drive to the Illinois Medical District and a 6-minute drive to the University of Illinois Chicago, with the United Centre a mere 10-minute walk away.
This 140-square-meter dwelling accommodates up to six guests across three bedrooms and features a fully equipped kitchen, high-speed Wi-Fi, and a deck and garden for relaxation.

This spacious Chicago residence is located near McCormick Place and the South Loop districts, 13 kilometres from Midway International Airport, and 2.2 kilometres from Guaranteed Rate Field and 3.9 kilometres from Grant Park.
This property offers 167 square metres of living space with accommodation for 12 guests, featuring a fully equipped kitchen with a fridge, microwave and dishwasher, air conditioning, a fitness centre, and Wi-Fi, with nearby cycling trails for exploration.

This five-bedroom Chicago house, sleeping twelve comfortably, is situated approximately 12 kilometres from Midway International Airport and a few kilometres from attractions such as the Museum of Science and Industry and Guaranteed Rate Field.
The 139-square-metre property boasts a fully equipped kitchen, four bathrooms, a balcony, free Wi-Fi, parking, and is ideal for large families or groups visiting the city.

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.

This Skokie dwelling is situated in a prime neighbourhood, offering easy access to major shopping centres such as Costco and Target, diverse dining options including Stefani Prime and Psistaria Greek Taverna, and excellent transport links with I-94 expressway access, a Metra train station 800 metres away, and the CTA Yellow Line, all within 16 kilometres of O'Hare International Airport. This family-friendly property accommodates up to six guests in three bedrooms and two bathrooms, featuring high-speed internet, two 70-inch smart 4K televisions, a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, air conditioning, in-unit laundry, a ping pong table, a cardio bicycle, and free parking, with keyless entry for a seamless check-in.

This three-storey townhome is located in Chicago's Lincoln Park neighbourhood, a 1.1 km walk from Lincoln Park Zoo, 1.9 km from North Avenue Beach, and approximately 3.5 km from both the 360 Chicago observation deck and the Water Tower.
The 130 square metre property boasts two bedrooms, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, private patio, in-unit laundry, free parking, and Wi-Fi.

This 4-bedroom modern urban escape is located in Chicago, offering city views and convenient access, approximately 2.7 kilometres from North Avenue Beach and 3.2 kilometres from Water Tower Chicago and 360 Chicago.
This detached house spans 112 square metres and accommodates up to 16 guests, featuring air conditioning, a kitchen with a fridge, microwave oven, and dishwasher, as well as an on-site water park and patio.

This five-bedroom home is located in Chicago's Old Town district, a short walk from North Avenue Beach, Oak Street Beach, and Lincoln Park Zoo. The property has received excellent ratings for location, cleanliness, and user experience.
This spacious dwelling covers 279 square metres and offers a range of amenities, including a fully-equipped kitchen, a private terrace, a garden, a spa, a restaurant, a fitness centre, and free parking.

This downtown Chicago holiday home is located a 10-minute walk from the Field Museum of Natural History and 1.4 kilometres from Grant Park, placing it conveniently close to the Art Institute of Chicago (1.4 kilometres), the Chicago Symphony Orchestra, DePaul University, and the Adler Planetarium & Astronomy Museum.
This 98 square metre, 2-bedroom, 2-bathroom apartment accommodates up to 8 guests and features a private patio with lake views, a well-equipped kitchen, air conditioning, complimentary Wi-Fi, and access to a shared lounge and sun terrace.

This luxurious eight-bedroom Chicago residence is situated 3.9km from Guaranteed Rate Field, 5km from Union Station, and 5.1km from the Field Museum, offering convenient access to major attractions.
The 418 square metre property boasts a spacious layout sleeping up to 16 guests, featuring a fully equipped kitchen, free Wi-Fi, a garden, and parking; ideal for large families or groups visiting the city.

This custom-built residence is located directly opposite Humboldt Park, offering extensive views of its pond and lake within Chicago.
This spacious dwelling accommodates up to 12 guests, featuring 5 bedrooms, 3 bathrooms, air conditioning, a fully equipped kitchen, and on-site parking, with a fitness centre available.

This Chicago townhouse, situated approximately 8-13 kilometres from Wrigley Field, Lincoln Park Zoo, and the United Centre, offers convenient access to major attractions.
Sleeping up to 17 guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, private parking, a fireplace, and a terrace/balcony; nearby activities include exploring Lincoln Park Zoo and catching a Cubs game at Wrigley Field.