Villas and Holiday homes in Chicago, IL

This Chinatown townhome offers three bedrooms and two bathrooms, sleeping eight guests comfortably, and is located minutes from Chicago's city centre, McCormick Place, and Ping Tom Park.
The property includes a fully equipped kitchen, private patio, in-unit laundry, high-speed Wi-Fi, and private parking, with numerous restaurants within a short walking distance.

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 Lakeview townhouse, a 10-minute walk (1.6km) from the Southport Corridor and Diversey CTA station, offers easy access to Chicago's Wrigleyville and Jewel-Osco supermarket.
The four-bedroom, three-bathroom property sleeps eight guests and features a spacious layout with high ceilings, a well-equipped kitchen, and a family room; nearby attractions include the Southport Corridor's shops and restaurants.

This River North duplex apartment in Chicago is ideally located within walking distance of the 360 Chicago Observation Deck and a short drive from Oak Street Beach, offering easy access to the city's key attractions.
The 167 square metre (1800 square foot) property features two bedrooms, three bathrooms, and sleeps up to 19 guests, boasting a fully equipped kitchen, in-unit laundry, air conditioning, a patio, and free Wi-Fi.

This three-bedroom Chicago cottage, located in the Bridgeport neighbourhood, offers easy access to public transport (62 bus and subway within 2km) and is a short drive (approx. 8km) from Millennium Park and McCormick Place, with Chinatown a 5-minute drive away.
The single-storey house sleeps six, features a kitchen with fridge, freezer and microwave, air conditioning, a garden, free parking for two cars in a detached garage plus street parking with a permit, and offers step-free access.

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.

This comfortable home is located near the border of Chicago and Oak Park, just a short distance from Hemingway's birthplace and a few minutes from several nearby suburbs. The property has received excellent user, location, and cleanliness ratings, ensuring a pleasant stay.
The house has two bedrooms and one bathroom, accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and internet access, allowing for a relaxing and enjoyable stay.

This spacious Chicago house, ideal for groups, offers four bedrooms and two bathrooms sleeping up to twelve guests, and boasts a 251-square-metre floor area across three floors.
The property includes a fully equipped kitchen, rooftop deck with city views, and convenient access to Chicago's attractions, though precise distances to landmarks are not specified.

This one-bedroom coach house is situated in Oak Park, a short walk from the L train and a local brewery, and a short drive from central Chicago.
The property features a full kitchen, a private patio, and a fenced-in parking spot, accommodating up to four guests.

This Greystone flat in Chicago is a 17-minute walk from Wrigley Field and a few kilometres from Lincoln Park Zoo, Loyola University Chicago, and Water Tower Chicago.
This three-bedroom, one-bathroom flat offers 93 square metres of living space, accommodates up to 11 guests, and includes a fully equipped kitchen and free WiFi.

This five-bedroom Chicago bungalow is located in the Beverly Hills neighbourhood, a 24km train journey from Chicago's city centre.
Sleeping up to 12 guests, this self-catering house boasts a fully-equipped kitchen, three-and-a-half bathrooms, a games room with pool table and air hockey, private deck, and parking; close to local shops and restaurants.

This five-bedroom Chicago house, located centrally and approximately 5-6 km from Lincoln Park Zoo, the Water Tower, and the United Centre, offers convenient access to major attractions.
The 340 square metre property boasts a fully equipped kitchen, four bathrooms, a private garden, two rooftop terraces, and comfortably accommodates up to 26 guests.