This restored coach house is located in Chicago's East Village, just a short walk from the shops and restaurants on Chicago Avenue and Damen Avenue. The property has received excellent ratings for cleanliness, location, and user experience. The house offers a spacious and open layout, perfect for up to four guests. It features a fully equipped kitchen, a dedicated office space, and a shared yard and patio, providing everything you need for a comfortable stay.
9.0 48 reviews
Chicago, IL
14/11 – 05/12
136 €/nighttotal: 2856 € (21 )
Lincoln Park Living - 3 Queen Beds - Sleeps 6
1 2
house , Chicago
This Lincoln Park holiday home in Chicago is ideally situated 1.9km from North Avenue Beach and 1.2km from Wrigley Field. The 93 square metre property offers three queen-size beds sleeping six, a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi, and a private patio; guests can easily access Lincoln Park Zoo (2.6km).
Chicago, IL
13/08 – 17/08
399 €/nighttotal: 1596 € (4 )
Westchester Retreat King Bed
3 2
house , Westchester
This Westchester holiday home is conveniently located 12 kilometres from O'Hare International Airport and within a 21-kilometre radius of Chicago landmarks such as Union Station, Willis Tower, and DePaul University. This one-bedroom property boasts 149 square metres of floor space, sleeping up to 11 guests and featuring two bathrooms, a fully equipped kitchen, garden, parking, and free Wi-Fi.
10 375 reviews
Chicago, IL
25/07 – 27/07
263 €/nighttotal: 526 € (2 )
Private Coach House Near Transit Shops & Nightlife
1 2
house , Chicago
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.
9.6 14 reviews
Chicago, IL
27/07 – 30/07
357 €/nighttotal: 1071 € (3 )
Beautiful Remodeled Penthouse Unit In Old Town
1 3
house , Chicago
This Chicago penthouse apartment, situated in the Old Town neighbourhood, is an 11-minute walk from North Avenue Beach and within 3.2 kilometres of attractions such as the Museum of Contemporary Art Chicago and the Magnificent Mile. The 111-square-metre property boasts three bedrooms, two bathrooms, sleeps 27 guests, and includes a fully equipped kitchen with dishwasher, free Wi-Fi, a washing machine, and air conditioning.
This Chicago apartment, ideally located in the West Loop, is a short distance (less than 2km) from Fulton Market's restaurants, the United Centre, Grant Park, Michigan Avenue and Lake Michigan. The 158 square metre property boasts three bedrooms, three bathrooms, sleeps up to twelve guests, and includes a fully equipped kitchen, private keyless entry, a car garage with EV charger, a roof deck with Willis Tower views, and a fenced backyard.
9.9 47 reviews
Chicago, IL
08/08 – 11/08
690 €/nighttotal: 2070 € (3 )
Chicago Wrigleyville Townhouse
1 6
house , Chicago
This Chicago townhouse, located in a safe neighbourhood a short walk from Wrigley Field and with easy access to public transport, offers a convenient base for exploring the city, including Lake Michigan and downtown Chicago. The spacious three-level property sleeps seven guests across two bedrooms and two bathrooms, featuring a fully equipped kitchen, free Wi-Fi, and streaming TV, plus free street parking with permits or optional paid garage parking.
Chicago, IL
29/09 – 02/10
287 €/nighttotal: 861 € (3 )
Lincoln Park Living - Suite 2
1 2
house , Chicago
House. You will be located in Chicago. Services and facilities include free parking, an iron and a kitchen. Take advantage of the air conditioning in this house!
Chicago, IL
08/07 – 12/07
515 €/nighttotal: 2060 € (4 )
Spacious 5br 2ba Berwyn Home
1 2
house , Berwyn
This 5-bedroom, 2-bathroom house in Berwyn is situated approximately 12 kilometres from Union Station and Willis Tower, 12 kilometres from Guaranteed Rate Field, and 12 kilometres from the United Center, offering convenient access to Chicago's key attractions. This spacious property provides accommodation for up to 14 guests, featuring a fully equipped kitchen, air conditioning, and free WiFi, with a floor area of 12 square metres.
Chicago, IL
21/09 – 24/09
666 €/nighttotal: 1998 € (3 )
Wicker Park 6bd 4ba, Steps From Cta, Parking Incl Home
6 6
house , Chicago
This Wicker Park residence offers excellent access to Chicago's public transport, situated just 3.7 kilometres from the United Centre and 4.2 kilometres from the Water Tower Chicago. This spacious property provides six bedrooms, four bathrooms, and parking for up to twenty-three guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and microwave, and complimentary WiFi.
9.9 117 reviews
Chicago, IL
27/06 – 06/07
241 €/nighttotal: 2169 € (9 )
Cozy 2 Bedroom House/w Garage In Skokie
1 2
house , Skokie
This Skokie Airbnb, situated on a quiet residential street, offers easy access to Downtown Chicago (40km) via Interstate 94, and is conveniently located near Village Crossing shopping centre (8km) and Old Orchard Mall (24km). This two-bedroom, one-and-a-half-bathroom property sleeps four guests and boasts a fully equipped kitchen, in-house gym, sauna, and attractive garden; enjoy free Wi-Fi and Roku TVs.
9.7 6 reviews
Chicago, IL
06/07 – 10/07
651 €/nighttotal: 2604 € (4 )
Boutique Garden House Chicago 3-story Sleeps 12
5 1
house , Chicago
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.
Best Chicago, IL villas and holiday homes with a pool
Among the 634 accommodations in Chicago, IL, here are the 4 best villas and holiday homes with a pool
9.9 23 reviews
Chicago, IL
25/06 – 02/07
250 €/nighttotal: 1750 € (7 )
Forest Park Oasis - Dog Friendly - Parks - The "L"
1 2
house , Forest Park
This newly renovated Forest Park townhouse is situated directly opposite Forest Park, Roos Recreation Centre, tennis courts and a swimming pool, and a 0.8 km walk from the Harlem Blue Line station, offering easy access to downtown Chicago and O'Hare Airport. The two-bedroom, one-bathroom property sleeps four, features a fully equipped kitchen with a bean-to-cup coffee machine, smart TVs, a dedicated workspace, a fenced yard with a pet door, and includes board games; free on-street parking supplements the designated parking space.
Chicago, IL
20/08 – 23/08
374 €/nighttotal: 1122 € (3 )
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill
2 2
apartment , Chicago
This Chicago detached house is located approximately 12 kilometres from the United Centre and 12.2 kilometres from Lincoln Park Zoo, offering straightforward access to several key city attractions. This detached house provides accommodation for up to 7 guests across 2 bedrooms, featuring a fully equipped kitchen with an oven and microwave, complimentary WiFi, and a backyard with a grill, all within a 1000 square metre floor area.
Chicago, IL
14/10 – 14/12
249 €/nighttotal: 15189 € (61 )
102 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 1
house , Des Plaines
Holiday house rental for 6 guests. You will be in Des Plaines. Services and facilities: a kitchen, a terrace and a swimming pool. This house also has air conditioning!
9.7 35 reviews
Chicago, IL
16/09 – 23/09
369 €/nighttotal: 2583 € (7 )
Andersonville Luxe Pool Escape
1 2
house , Chicago
This chic Andersonville townhouse, a short walk from the beach and close to Andersonville's shops and restaurants, offers convenient access to Chicago's attractions. The one-bedroom, one-bathroom property features a private heated pool and spa, a full kitchen with freezer, microwave, and dishwasher, high-speed Wi-Fi, and parking; it comfortably sleeps two guests and offers the option to rent the pool and yard for parties.
Best family friendly Chicago, IL villas and holiday home
Among the 634 accommodations in Chicago, IL, here are the 4 best family friendly villas and holiday homes
9.9 155 reviews
Chicago, IL
11/09 – 13/09
2067 €/nighttotal: 4134 € (2 )
Chicago Bootlegger House Sleeps 10-20
1 11
bungalow , Chicago
This six-bedroom house is located in a lively neighbourhood, just a short walk from Lake Michigan, Lincoln Park Zoo, Wrigley Field, and the Red Line train. It has received excellent ratings for location, cleanliness, and overall user experience. This spacious property can comfortably accommodate up to sixteen guests and features a fully equipped kitchen, a private rooftop deck, and a range of entertainment options including a foosball table, vintage slot machine, board games, and a working fireplace.
This stylish three-bedroom apartment in Chicago's trendy Bucktown neighbourhood offers easy access to the city's attractions, though precise distances aren't specified. Sleeping six comfortably, this mid-century modern flat boasts a chef's kitchen, in-unit laundry, and optional access to a private speakeasy; enhanced security features and a sunroom complete the offering.
Chicago, IL
28/06 – 01/07
365 €/nighttotal: 1095 € (3 )
Cozy Downtown Mich Ave Gym And Rooftop #7
2 2
house , Chicago
This apartment is located in central Chicago, 966 metres from Grant Park and the Art Institute of Chicago, and within a 30-minute walk of the CIBC Theatre and Millennium Park. This holiday home offers 64 square metres of living space with 2 bedrooms, 2 bathrooms, and can accommodate up to 7 guests, featuring a fully equipped kitchen, WiFi, and a fitness centre.
Chicago, IL
01/08 – 31/10
263 €/nighttotal: 23933 € (91 )
186 M² House ∙ 3 Bedrooms ∙ 10 Guests
3 2
house , Lincolnwood
Holiday house rental for 10 people. This accommodation is located in Lincolnwood. Facilities and services include a kitchen, a fridge and a dish washer. Take advantage of the air conditioning in this house!
Frequently asked questions about villa rentals in Chicago, IL
What are the must-see attractions in Chicago, IL?
You simply can't miss the iconic Willis Tower, formerly known as the Sears Tower, for breathtaking views of the city. The Art Institute of Chicago is a must for any art enthusiast, housing masterpieces like Edward Hopper's 'Nighthawks'. And of course, no visit to Chicago is complete without strolling along Navy Pier, enjoying the Ferris wheel and vibrant atmosphere.
What indoor activities for families are available in Chicago, IL on rainy days?
The Shedd Aquarium is a fantastic choice, showcasing a wide range of marine life. The Field Museum, home to Sue the T-Rex, offers an engaging journey through natural history. For a more interactive experience, the Museum of Science and Industry is always a hit, with its fascinating exhibits and hands-on activities.
What are the best villa rentals with a pool in Chicago, IL?
Chicago is a city that truly has something for everyone. You can catch a Cubs game at Wrigley Field, explore the vibrant street art scene in the Pilsen neighbourhood, or enjoy a relaxing boat tour on the Chicago River. For a cultural experience, the Lyric Opera of Chicago and the Goodman Theatre offer world-class performances.
What are the best villa rentals with a jacuzzi in Chicago, IL?
What are the advantages of renting a house or a villa in Chicago, IL
Renting a house or villa in Chicago offers more space and privacy compared to a hotel, perfect for families or groups. You'll have access to a kitchen for preparing meals, saving on dining costs. Many rentals also come with amenities like laundry facilities and outdoor spaces, adding to the comfort and convenience of your stay.
What are the best villa rentals for families and kids in Chicago, IL?
What food festivals or culinary events take place in and around Chicago, IL?
The Taste of Chicago is a massive food festival held in Grant Park, showcasing the city's diverse culinary scene. The Chicago Gourmet, held in Millennium Park, is another popular event featuring top chefs and restaurants. For a more intimate experience, the Chicago Food & Wine Festival offers tastings and cooking demonstrations.
What are the best pet friendly villa rentals in Chicago, IL?
What exclusive experiences are available when visiting Chicago, IL?
For a truly unique experience, you can book a private tour of the Chicago Theatre, a historic landmark with stunning architecture. You can also enjoy a behind-the-scenes tour of the Wrigley Field, home of the Chicago Cubs, and learn about the team's history and traditions.
What are the best villa rentals with parking in Chicago, IL?
Which part of Chicago, IL would be ideal for a villa rental?
Lincoln Park is a great option for a villa rental, offering a peaceful residential area with easy access to the lakefront, parks, and cultural attractions. The Gold Coast is another popular choice, known for its luxury boutiques and upscale restaurants.
Destinations nearby
Best Chicago, IL villas and holiday homes with parking
Chicago, IL
20/06 – 25/07
534 €/nighttotal: 18690 € (35 )
102 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 1
house , Elmhurst
Holiday house for up to 6 people. You will be based in Elmhurst. Services and facilities: a fridge, air conditioning and a terrace.
Chicago, IL
19/08 – 18/12
109 €/nighttotal: 13189 € (121 )
74 M² House ∙ 2 Bedrooms ∙ 4 Guests
2 2
house , Forest Park
Book this Holiday rental for up to 4 people. This accommodation is located in Forest Park. Services and facilities: a freeze, free parking and air conditioning. Take advantage of the garden in this house!
Chicago, IL
05/01 – 28/02
295 €/nighttotal: 15930 € (54 )
82 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 2
house , Oak Park
Book this Holiday rental for up to 8 guests. This accommodation is located in Oak Park. Facilities and services: a dish washer, air conditioning and free parking.
9.0 3 reviews
Chicago, IL
01/07 – 07/07
427 €/nighttotal: 2562 € (6 )
Spacious Chicago Condo With Deck Less Than 9 Mi To Downtown!
4 2
apartment , Chicago
This Oak Park condo, situated less than 14.5 kilometres from Chicago's city centre and iconic landmarks such as the Willis Tower and Union Station, offers easy access to major attractions. The 186-square-metre property boasts four bedrooms, two bathrooms, sleeps 23 guests, includes a fully equipped kitchen with dishwasher, and offers free Wi-Fi, in-unit laundry, and a private outdoor dining area; nearby amenities include the United Centre, just 10 kilometres away.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL villas and holiday homes with a garden
10 2 reviews
Chicago, IL
12/08 – 15/08
1522 €/nighttotal: 4566 € (3 )
Stunning 5br Home In Heart Of Chicago With 2 Rooftops
1 2
house , Chicago
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.
10 226 reviews
Chicago, IL
13/07 – 15/07
231 €/nighttotal: 462 € (2 )
Lovely Central Oak Park Th W/parking & On Green El
1 5
house , Oak Park
This charming house is located in a central Oak Park neighbourhood, just a short walk from the Green Line, Metra, and the Oak Park Farmers Market. It has received excellent ratings for location, cleanliness and user experience. The property has two bedrooms and two bathrooms, making it ideal for families or groups of up to five people. It comes equipped with a kitchen, a garden, parking, and laundry facilities, as well as air conditioning and internet access.
Chicago, IL
10/08 – 10/10
167 €/nighttotal: 10187 € (61 )
Charming Andersonville Coach House 3br 2,5ba
3 2
house , Chicago
This private, two-storey coach house in Chicago is located on a quiet, tree-lined street, less than 300 metres from the dining, shopping, and café options on North Clark. This dwelling offers three bedrooms, two and a half bathrooms, and accommodates up to five guests, with internet, air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher, plus it allows pets for an additional fee.
10 3 reviews
Chicago, IL
01/09 – 05/09
513 €/nighttotal: 2052 € (4 )
Modern 2-bedroom Townhome In Chicago With Private Patio
1 2
apartment , Chicago
This Bucktown townhouse, situated on a quiet corner block within easy walking distance of the Six Corners intersection of North, Milwaukee, and Damen Avenues, offers a convenient base for exploring Chicago. This 167 square metre (1798 square foot) property sleeps up to nine guests, boasting two living rooms, three bathrooms, a fully equipped kitchen with coffee station, a private patio with fire pit, a game room with shuffleboard and Connect 4, and free street parking.
