Vacation Homes and Villa Rentals in Chicago, IL

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 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 modern house is situated in the RiverWest neighbourhood, a short walk from the Chicago Avenue Blue Line station and minutes from downtown Chicago. It has consistently received excellent ratings for location, cleanliness and user experience.
This spacious property offers four bedrooms and three and a half bathrooms, providing ample space for a group of travellers. The house features a fully equipped kitchen, a luxurious jacuzzi, a private garden and a terrace, ensuring a comfortable and enjoyable stay.

This six-bedroom property is situated in the trendy Logan Square neighbourhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and the United Center. The house has consistently received excellent ratings for its cleanliness, location, and overall experience.
The spacious home spans 300 square metres and can comfortably accommodate up to 16 guests. It includes a fully equipped kitchen, a garden, a terrace, air conditioning, and free parking, making it a perfect choice for families or groups exploring Chicago.

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 charming house is situated in the trendy Logan Square neighbourhood, just a short walk from Milwaukee Avenue and the 606 Trail. The property has received excellent ratings for location, cleanliness, and user experience.
This comfortable three-bedroom home comfortably sleeps up to eight guests. The property features a fully equipped kitchen, a private garden, and a secure parking space. Enjoy the convenience of self check-in, Netflix and Amazon Prime, as well as easy access to public transport.

This townhouse is perfectly situated in downtown Chicago, just a short walk from Oak Street Beach and 360 Chicago, with other popular attractions easily accessible. The property consistently receives excellent ratings for its location, cleanliness, and user experience.
The townhouse offers ample space with five bedrooms and three bathrooms, ideal for families or groups. Guests can enjoy modern amenities like a fully equipped kitchen, free Wi-Fi, air conditioning, and even a spa, making it a comfortable and convenient base for exploring the city.

This charming bungalow is situated in a peaceful, tree-lined neighbourhood in the south suburbs of Chicago, just 20 minutes from the city centre and close to major transport links. It consistently receives excellent ratings for cleanliness, location and overall user experience.
The property offers three bedrooms and one bathroom, comfortably accommodating up to eight guests. Amenities include a well-equipped kitchen, air conditioning, a sunny porch, a garden and on-site parking.

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 three-bedroom townhouse is situated in Edgewater, a lively neighbourhood in Chicago, just a short distance from the lakefront and within easy reach of several universities. The property has received excellent ratings for its cleanliness, location and overall experience.
The accommodation offers plenty of space for families or groups of up to 10 guests. The kitchen is well-equipped with modern appliances, and the living areas provide comfortable spaces for relaxing and socialising. Guests can enjoy a private garden, off-street parking and a range of amenities perfect for families, including a high chair, toys and a pack 'n' play.

This Oak Park bungalow is located on a peaceful street just a short drive from downtown Chicago and O'Hare Airport, making it a convenient base for exploring the city and beyond. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The spacious home features four bedrooms, sleeping up to nine guests, and a large kitchen with modern appliances. Guests can enjoy the convenience of a dishwasher, a washing machine and dryer, and a fully equipped kitchen, as well as the relaxing outdoor space with a gazebo.

This newly renovated house is located in East Garfield Park, a neighbourhood in Chicago, just 5 minutes from the United Center and 15 minutes from downtown. It has received excellent user ratings and is perfect for families visiting the city.
This comfortable home has three bedrooms and sleeps eight people. It offers modern amenities including internet, a fully equipped kitchen, air conditioning, a spa, and parking.

This charming bungalow is located in a quiet historic district in Chicago, just 15-20 minutes from the Lake, Downtown, Wrigley Field, United Center, Oak Park, Soldier Field, and Sox Park. The apartment consistently receives excellent ratings for cleanliness, location, and user experience.
This two-storey home offers 223 square metres of space, including three bedrooms, two bathrooms, and a large walk-in closet. The apartment is family-friendly, with amenities such as a pack-and-play, stroller, highchair, a pull-out bed in the living room, a private backyard with a deck, and a garage for one vehicle.

This tower is located in Downtown Chicago, just a short walk from Michigan Avenue and Navy Pier, making it ideal for exploring the city's best attractions. It has excellent user ratings, making it a popular choice for travellers.
The apartment has one bedroom and one bathroom, with a floor area of 30 square metres, comfortably accommodating up to two guests. It offers a range of amenities, including a swimming pool, gym, restaurant, bar, and sun terrace, ensuring a comfortable and enjoyable stay.

This tower is situated in Downtown Chicago, just a short walk from Michigan Avenue and Navy Pier, offering easy access to the city's main attractions. The area is vibrant and bustling, with plenty of shops, restaurants, and entertainment options.
The apartment is modern and stylish, with one bedroom, one bathroom, and a living area, providing comfortable accommodation for up to three guests. The apartment has a range of amenities, including a swimming pool, fitness centre, and parking, making it a great choice for families and groups.

This tower is situated in the heart of Downtown Chicago, just a short stroll from Michigan Avenue and Navy Pier, with Millennium Park and Lake Michigan easily accessible.
The one-bedroom apartment offers 59 square metres of space, comfortably accommodating up to three guests. The tower provides a range of amenities, including a rooftop pool, a fitness centre, a restaurant, a bar, and parking.

This modern house is located in the RiverWest neighbourhood, just a minute's walk from the Blue Line, offering easy access to downtown Chicago and its vibrant nightlife. The property has received excellent ratings for location, cleanliness and user experience.
The four-bedroom property spans 251 square metres and includes a gourmet kitchen, Jacuzzi tub, multiple decks with city views, and a natural gas grill. Guests can enjoy high-speed Wi-Fi, flat-screen TVs in every bedroom, and a built-in espresso machine, perfect for a relaxing stay.

This upscale residence is located in Chicago, just a short distance from Wrigley Field and Lincoln Park Zoo, offering easy access to the city's attractions and a peaceful neighbourhood atmosphere. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The home features five bedrooms and five bathrooms spread across 353 square metres of living space. Amenities include a fully equipped kitchen, a spa bath, a hot tub, a garden, a terrace, and parking, ensuring a comfortable and enjoyable stay for large groups or families.

This Chicago beach house is located in the Rogers Park neighbourhood, just a short walk from Lake Michigan and Loyola Park, offering a peaceful escape from the hustle and bustle of the city. The property has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The house has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. It boasts a fully equipped kitchen, a spacious garden with a fire pit, and a fitness room, ensuring a relaxing and enjoyable stay for families and groups.

This spacious house in Lincoln Park is ideally located just 15 blocks from Wrigley Field, 5 blocks from the Kennedy Expressway, and 6 blocks from the EL, making it easy to explore the city. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
This four-bedroom home spans 390 square metres and comfortably accommodates up to 24 guests. The house offers a range of amenities, including a private garage, a fully equipped kitchen, a jacuzzi, a terrace, a garden, and a spa, ensuring a relaxing and enjoyable stay.

This two-bedroom apartment is ideally located in the Southport Corridor, a lively neighbourhood just a short walk from Wrigley Field and the Brown and Red line trains. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably sleeps six guests with its three beds and a spacious deck. Guests can enjoy a fully equipped kitchen, a large TV with streaming services, a washer/dryer, and a private garage with an EV charger for an additional fee.

This three-bedroom townhouse is situated in Edgewater, a vibrant neighbourhood on Chicago's North Side, just four miles from Evanston and Northwestern University. The property has received excellent ratings for location, cleanliness, and user experience.
The townhouse offers ample space for families or groups, comfortably accommodating up to 10 guests. Amenities include a well-equipped kitchen, a fitness centre, a garden, parking, and a range of family-friendly extras such as a high chair and toys.

This four-storey townhouse is located in Chicago's East Village, a short walk from the Milwaukee 'L' station and a 12-minute subway ride from the Loop, Michigan Avenue, and the Lakefront. It has consistently received excellent user ratings for location, cleanliness, and overall experience.
The property offers 223 square metres of living space, comprising four bedrooms and five bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, private terraces, a spa-like bathroom, a fireplace, games, and a Sonos sound system.

This charming coach house is situated in Wicker Park, a popular neighbourhood known for its lively bars, restaurants, and shops, and is just a short walk from the Blue Line train station, providing easy access to downtown Chicago and O'Hare Airport. It has received excellent user ratings and is a great option for travellers looking for a comfortable and convenient base in the city.
The property offers 82 square metres of space, accommodating up to five guests in two bedrooms and one bathroom. Guests can enjoy a private deck with a Weber grill, a fully equipped kitchen with a fridge, microwave, and dishwasher, and a range of amenities including central air conditioning, WiFi, smart TVs, and a washer and dryer.

This comfortable home is situated in a convenient suburban area near Rosemont, just a short 10-minute drive from the Rosemont Convention Center and Fashion Outlet, making it ideal for both business and leisure travellers. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The house offers two bedrooms and one bathroom, comfortably accommodating up to four guests. Modern amenities include a fully equipped kitchen, air conditioning, parking, and high-speed internet, ensuring a comfortable and convenient stay.

This stylish townhouse is situated in Chicago's River West neighbourhood, just a short walk from the vibrant West Loop, River North, and the Loop, offering easy access to the city's best restaurants, bars, and attractions. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The property is spread across three floors, offering four bedrooms and five beds, comfortably accommodating up to 10 guests. The townhouse features a modern design, a private patio, a fully equipped kitchen, and a private garage, ensuring a comfortable and convenient stay.

This Gold Coast property is located in central Chicago, just a short walk from Oak Street Beach and North Avenue Beach, offering easy access to the vibrant Magnificent Mile shopping district and renowned restaurants. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The spacious four-bedroom house has a floor area of 223 square metres and can comfortably accommodate up to 10 guests. The house features a fully equipped kitchen, a private terrace with inner courtyard views, free parking in a garage, and a flat-screen TV with streaming services, providing everything you need for a comfortable and enjoyable stay.

This family-friendly house is located in central Berwyn, just six miles from the Frank Lloyd Wright Historic District, Anna and Frederick Douglass Park, and Concordia University Chicago. This property has received excellent ratings for location, cleanliness, and user experience.
The house has four bedrooms and can comfortably accommodate eight guests, offering 214 square metres of living space. You can enjoy a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and a fully equipped kitchen.

This three-bedroom house is situated in Chicago, just five miles from the city centre and a short distance from the United Center. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The house provides 139 square metres of space, accommodating up to five guests. It features a fully equipped kitchen, a private patio and garden, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay.

This charming townhome is located in the popular Old Town neighbourhood, just a short walk from Wells Street, North Avenue, Lincoln Park, and the lakefront. The property has excellent ratings for location, cleanliness, and user experience.
The two-level house comfortably accommodates up to six guests and features a fully equipped kitchen, dedicated workspaces in each bedroom, and on-site laundry facilities. Guests can enjoy the convenience of free parking, a terrace, a garden, and air conditioning.

This two-bedroom apartment is located in Lincoln Park, Chicago, a peaceful residential area just three miles from 360 Chicago and Water Tower Chicago. It has received excellent reviews from previous guests.
The apartment is 121 square metres and can accommodate up to four guests. Amenities include a fully equipped kitchen, free Wi-Fi, air conditioning, a terrace, a garden, and private parking.

This charming house, located in a former coach house just four miles from downtown Chicago's Loop, offers a unique glimpse into the city's history and is situated near Humboldt Park, a vibrant green space. It has consistently received excellent ratings for its location, cleanliness, and user experience.
The property provides comfortable accommodation for up to four guests, with two bedrooms and a bathroom. It features modern amenities, including a dishwasher, coffee maker, washer/dryer, and a smart TV, as well as a private garden patio for relaxing outdoors.