Villas and Holiday homes in Chicago, IL

This luxury penthouse is located in Chicago's River North district, offering spectacular city views from a private roof deck and convenient access to downtown attractions.
This stylish accommodation spans 167 square meters and features three bedrooms, a fully equipped kitchen, air conditioning, parking, and is within walking distance of River North's dining and entertainment.

The Avondale Guesthouse is situated in the Avondale neighbourhood of Chicago, just a short distance from Wrigley Field and Lincoln Park Zoo, making it a great base for exploring the city. The guesthouse consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The property has three bedrooms, accommodating up to six guests, and is ideal for families or groups of friends. You can enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, and a private patio, as well as explore the neighbourhood by bike or relax in the garden.

This charming Chicago property is situated in a family-friendly neighbourhood, just 25 kilometres from O'Hare airport, with convenient access to public transport for exploring Wrigleyville and the city centre. It has consistently received excellent ratings for location, cleanliness, and overall experience.
This three-bedroom home comfortably accommodates up to six guests. It offers a range of amenities including a fully equipped kitchen, air conditioning, a garden, and parking, ensuring a comfortable and enjoyable stay.

This family-friendly holiday home in Brookfield is conveniently located 20.9 kilometres from Guaranteed Rate Field and United Center, and 10.9 kilometres from Midway International Airport.
This spacious 204 square metre property offers four bedrooms, two bathrooms, a fully equipped kitchen with a fridge and dishwasher, air conditioning, free WiFi, and on-site parking, with the added benefit of a garden and outdoor dining area.

This Chicago holiday home is located 9.6 kilometres from Wrigley Field, offering easy access to attractions such as Lincoln Park Zoo (14.2 km) and Union Station (15.1 km).
This spacious property spans 1000 square metres, accommodating up to 18 guests across 8 bedrooms, and features a dedicated gym, a games room with billiards and table tennis, and a cinema.

This Roscoe Village detached house is situated within easy walking distance of numerous eateries, shops, and a Starbucks, with the Brown Line train station a mere 500-meter stroll away for convenient access to downtown Chicago.
This residence offers two floors of living space, accommodating up to six guests with flexible bedding, and boasts a chef's kitchen, a spacious deck, and a grass yard complete with a full-size barbecue.

This Wicker Park townhouse is located on a historic, tree-lined street, 800 meters from the El train and a short drive from the motorway, providing convenient access to Chicago's attractions.
This family-friendly accommodation sleeps six and offers three bedrooms, two bathrooms, a fully equipped chef's kitchen, a Peloton, and two private rooftop terraces with city views.

This charming loft-style coach house is located in a former church rectory, a short distance from Chicago's bustling downtown area. It has consistently received excellent ratings for user experience, location, and cleanliness.
The property comfortably accommodates up to seven guests with two bedrooms and two bathrooms. Enjoy modern amenities including a washer and dryer, a "pack & play" for infants, street parking, and a basketball court and side yard available for guest use with prior permission.

This penthouse apartment offers a prime downtown Chicago location, situated 1.4 kilometres from the Field Museum and 1.4 kilometres from Cloud Gate, with Grant Park a 10-minute walk away.
This air-conditioned property features free WiFi, a fully equipped kitchen, one bedroom, one bathroom, and can accommodate up to three guests, with a fitness centre also available.

This Chicago flat is located near the University of Illinois Chicago (UIC) campus, offering convenient access within 3.4 kilometres of Willis Tower and 4 kilometres of Union Station.
This 116 square metre apartment accommodates up to seven guests with two bedrooms and two bathrooms, featuring air conditioning, a fully equipped kitchen, complimentary Wi-Fi, and an outdoor swimming pool.

This private coach house in Chicago provides a unique and exclusive stay, offering abundant natural light and a quiet atmosphere within a highly walkable district with easy Metra access for efficient travel.
This distinctive one-bedroom, one-bathroom dwelling accommodates up to four guests and includes a kitchen with a fridge, freezer, microwave, and dishwasher, plus complimentary garage parking.

This newly renovated coach house in Chicago's Wicker Park/Logan Square neighbourhood is a 7-minute walk from the CTA Blue Line 'L' train, offering easy access to O'Hare Airport and the city centre.
The 70 square metre property sleeps three adults comfortably, features a well-equipped kitchen, modern amenities including 100 Mbps fibre internet, keyless entry and a private balcony, and provides daily parking passes.