Villas and Holiday homes in Chicago, IL

This Wicker Park house, in Chicago, Illinois, is conveniently located near the CTA public transport system and within 3-5 km of the United Centre, Water Tower Place, and Union Station.
Sleeping up to 13 guests, this four-bedroom, three-bathroom property boasts free Wi-Fi, private parking, a fully equipped kitchen including a dishwasher and microwave, and a private entrance.

This apartment is located in Chicago, just 3.4 kilometres from Lincoln Park Zoo and 4.3 kilometres from United Center, offering easy access to attractions and a vibrant neighbourhood. It has received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom flat, spanning 139 square metres, comfortably accommodates up to 11 guests. It features a private speakeasy and garden, a bespoke travel lodge design, an outdoor fireplace, a spacious interior, a private entrance and patio, continental breakfast and BBQ facilities, and pet-friendly accommodations.

This West Town townhouse, situated 4km from downtown Chicago, offers easy access to the city's attractions.
Sleeping six guests, this three-bedroom, two-bathroom property boasts three outdoor spaces – a patio with fireplace, kitchen balcony, and rooftop deck – plus a high-end kitchen, private parking, and child-friendly amenities available on request.

This spacious four-bedroom apartment in Chicago offers convenient access to North Avenue Beach, located 2.7 kilometres away, and is within 3.4 kilometres of Water Tower Chicago and the Museum of Contemporary Art.
This property provides a fully equipped kitchen, air conditioning, free WiFi, a fitness centre, and on-site casino and water park facilities, with a floor area of 130 square metres and capacity for 15 guests.

This Foursquare property in Forest Park offers convenient access to the Blue Line, situated less than 1 kilometre away, providing straightforward journeys to downtown Chicago landmarks such as Union Station and the Willis Tower, both 16 kilometres distant, and the United Centre, 12.7 kilometres away.
This 104 square metre holiday home accommodates up to 13 guests with three bedrooms and two living rooms, featuring a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, free WiFi, a private patio, and an outdoor dining area, with Midway International Airport 13.9 kilometres distant.

This Skokie house enjoys a prime location near major shopping centres including Costco, Target and Walmart, a short 16km drive from O'Hare International Airport and 21km from downtown Chicago.
The three-bedroom, two-bathroom property sleeps six guests and offers a fully equipped kitchen, a furnished basement with ping pong table and exercise bike, two 70-inch smart TVs, keyless entry, and free parking.

This private coach house in Chicago's Lincoln Park district is located a short walk from DePaul University and Pequod's Pizza, offering convenient train access to Downtown and Wrigley Field.
This one-bedroom, one-bathroom cottage accommodates up to four guests and features a fully stocked kitchen, air conditioning, parking, and a patio, with easy access to public transport and local attractions.

House rental listing. You will be based in Chicago.
Facilities and services: a fridge, a terrace and a dish washer. Take advantage of the Free Parking with this accommodation.

This spacious home is located in a safe and convenient neighbourhood on the border of Andersonville, Edgewater, and Rogers Park, just a short distance from Little India, Loyola University, and Northwestern University. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment has five bedrooms, two kitchens, and two dining rooms, making it perfect for families or groups. Guests can enjoy a living room, a sunroom, a garden, a fitness centre, and parking, as well as access to the internet and air conditioning.

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 Wicker Park residence is situated just steps from shops and nightlife, offering a 10-20 minute drive or transit ride to downtown Chicago landmarks such as Millennium Park and the Magnificent Mile.
This spacious 5-bedroom property accommodates up to 16 guests, featuring a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a jacuzzi, terrace, sauna, and private parking, alongside an entertainment basement with air hockey and foosball.

This 2-bedroom, 2-bathroom apartment is located in Downtown Chicago, a 10-minute walk from the Field Museum of Natural History and 1.4 kilometres from the Art Institute of Chicago, offering direct lake views.
This 98 square metre property accommodates up to 8 guests and includes a kitchen with a fridge, microwave, and dishwasher, as well as complimentary WiFi and a shared lounge area.