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Villas and Holiday homes in Chicago, IL

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772 Villa rentals in Chicago, IL

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
Chicago, IL
3 2
£190/nighttotal: £2090 (11 )

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill

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.
Stunning Duplex Condo #1 - Downtown River North - Chicago, IL
9.4 27 reviews
Chicago, IL
2 1
£237/nighttotal: £948 (4 )

Stunning Duplex Condo #1 - Downtown River North

house - Chicago
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.
Spacious Backyard Oasis And Entertainment Haven - Elegant Luxury Retreat - Chicago, IL
Chicago, IL
6 7
£503/nighttotal: £2012 (4 )

Spacious Backyard Oasis And Entertainment Haven - Elegant Luxury Retreat

house - Chicago
This seven-bedroom Bridgeport dwelling is situated in Chicago's Pilsen district, offering convenient access to the city centre via the Ashland Orange Line, approximately 32 to 48 kilometres from Midway Airport and 64 to 96 kilometres from O'Hare Airport by car.
This family-friendly house accommodates up to 16 guests and features two kitchens, a pool table, a private garden with a barbecue, and is equipped with air conditioning, a jacuzzi, and a sauna for your comfort.
House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
Chicago, IL
1 3
£131/nighttotal: £13886 (106 )

House ∙ 3 Bedrooms ∙ 6 Guests

house - Skokie
This detached house in Skokie offers a peaceful residential setting with easy street parking, situated a mere 3.86 kilometres from O'Hare Airport and within a 1.45 kilometre drive to Northwestern University and Loyola University, and 1.93 kilometres to Wrigley Field.
This guest-favourite property, rated 4.95 stars, accommodates up to six guests across three bedrooms, featuring a fully equipped kitchen, a sun deck, and amenities including high-speed Wi-Fi and self check-in for a comfortable stay.
Envitae Hotel 4br Modern Sleek Apartment - Chicago, IL
Chicago, IL
2 4
£426/nighttotal: £1278 (3 )

Envitae Hotel 4br Modern Sleek Apartment

house - Chicago
This apartment in Chicago is situated 2.7 kilometres from North Avenue Beach and 3.2 kilometres from Water Tower Chicago and 360 Chicago.
Spanning 130 square metres, this property offers four bedrooms, three bathrooms, and accommodates up to 16 guests, featuring a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, free WiFi, and an on-site fitness centre, with a water park and cycling opportunities nearby.
Spacious 8 Bdr + 2 Kitchens + Garage! Sleeps 16! - Chicago, IL
9.6 12 reviews
Chicago, IL
3 1
£1740/nighttotal: £8700 (5 )

Spacious 8 Bdr + 2 Kitchens + Garage! Sleeps 16!

house - Chicago
This eight-bedroom Avondale townhome, situated approximately 24 kilometres from O'Hare International Airport and two blocks from a major highway, offers easy access to Chicago's restaurants and attractions.
Sleeping sixteen guests comfortably, this spacious property boasts two fully equipped kitchens, two garage spaces, extensive amenities including fresh linens and streaming TV, and self check-in via keypad.
House 5bed/3bath/1parking Close To Downtown & Lake - Chicago, IL
9.8 310 reviews
Chicago, IL
5 5
£376/nighttotal: £2256 (6 )

House 5bed/3bath/1parking Close To Downtown & Lake

house - Chicago
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.
Charming & Bright Multilevel Townhome With Parking - Chicago, IL
Chicago, IL
6 2
£559/nighttotal: £1677 (3 )

Charming & Bright Multilevel Townhome With Parking

house - Chicago
This Chicago townhome is situated near Lincoln Park, approximately 1.8 kilometres from Lincoln Park Zoo and within a 3-5 kilometre radius of Water Tower Place and the Magnificent Mile.
The two-bedroom, two-bathroom property sleeps eleven guests, offering free Wi-Fi, on-site parking, a fully equipped kitchen with dishwasher and microwave, and air conditioning.
King Bed L Cta L United Center L Near Kasama L Patio - Chicago, IL
Chicago, IL
2 2
£423/nighttotal: £1692 (4 )

King Bed L Cta L United Center L Near Kasama L Patio

house - Chicago
This Chicago residence is situated 2.6 kilometres from the United Center and within 4.5 kilometres of the Chicago Water Tower and Union Station, offering convenient access to downtown attractions.
This property provides accommodation for up to 9 guests across 2 bedrooms, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, complimentary Wi-Fi, air conditioning, a private patio, and parking, with a floor area of 15 square meters.
102 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
Chicago, IL
2 3
£323/nighttotal: £19703 (61 )

102 M² House ∙ 3 Bedrooms ∙ 6 Guests

house - Elmhurst
House rental for 6 guests. You will be located in Elmhurst.
Services and facilities: a fridge, a freeze and free parking. Take advantage of the air conditioning in this house in Elmhurst.
Entire House In Lakeview With Yard And Garage - Chicago, IL
9.7 107 reviews
Chicago, IL
1 3
£236/nighttotal: £7316 (31 )

Entire House In Lakeview With Yard And Garage

house - Chicago
This Chicago house, ideally located in a trendy neighbourhood near Wrigleyville and Boystown, is within easy walking distance of a train station offering quick access (under 20 minutes) to the city centre.
The three-level property boasts three bedrooms, three bathrooms, and sleeps eight guests, featuring a jacuzzi, private parking, super-fast Wi-Fi (659 Mbps), and a backyard deck with a grill; nearby amenities include Target and Starbucks.
Luxury River West Townhome With Garage - Chicago, IL
9.9 262 reviews
Chicago, IL
4 4
£618/nighttotal: £3090 (5 )

Luxury River West Townhome With Garage

house - Chicago
This charming house is situated in River West, a trendy neighbourhood just 3km from the Chicago Loop, easily accessible by public transport. It has received excellent ratings for location, cleanliness and overall user experience.
The property offers 4 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. Amenities include a private garage, a rooftop deck with city views, a Yamaha grand piano, a fully equipped kitchen, a jacuzzi tub, a workspace, and laundry facilities.

Find Holiday Homes in the City Centre of Chicago, IL

Stay right next to popular local bistros and top landmarks with central holiday homes in Chicago, IL.

Downtown Park - Mich Ave Ph Gym Plus Rooftop #11 - Chicago, IL
10 1 review
Chicago, IL
2 1
£344/nighttotal: £2408 (7 )

Downtown Park - Mich Ave Ph Gym Plus Rooftop #11

house - Chicago
This downtown Chicago apartment offers a prime location, a 17-minute walk from Cloud Gate and 1.4 kilometres from CIBC Theatre, with Grant Park a 9-minute walk away and the city centre within 1.9 kilometres.
This 33 square metre flat accommodates up to five guests, featuring one bedroom and one bathroom, a fully equipped kitchen with a dishwasher, air conditioning, and access to an on-site fitness centre, with complimentary WiFi throughout.
Downtown Lake Views, Mich Ave, Museums 2bd- 2ba #10 - Chicago, IL
10 1 review
Chicago, IL
2 2
£368/nighttotal: £1104 (3 )

Downtown Lake Views, Mich Ave, Museums 2bd- 2ba #10

house - Chicago
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.
Breathtaking Downtown Penthouse B - Sleeps 11 - Chicago, IL
9.2 19 reviews
Chicago, IL
2 1
£372/nighttotal: £6324 (17 )

Breathtaking Downtown Penthouse B - Sleeps 11

house - Chicago
This downtown Chicago penthouse, approximately 2.4 kilometres from Ohio Street Beach and 2.9 kilometres from North Avenue Beach, offers easy access to attractions such as the Oak Street Beach and the Museum of Contemporary Art.
This 167 square metre three-bedroom, three-bathroom dwelling sleeps eleven, features a fully equipped kitchen, patio, free Wi-Fi, and parking, making it ideal for large groups or families visiting the city.
Historic Luxury Townhouse In Downtown Chicago - Chicago, IL
9.6 350 reviews
Chicago, IL
3 4
£810/nighttotal: £8910 (11 )

Historic Luxury Townhouse In Downtown Chicago

house - Chicago
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.

Best family friendly Chicago, IL villas and holiday home

Among the 772 accommodations in Chicago, IL, here are the 4 best family friendly villas and holiday homes

Spacious Oasis With Deck And Backyard - Stylish Comfort Retreat - Chicago, IL
Chicago, IL
4 3
£294/nighttotal: £882 (3 )

Spacious Oasis With Deck And Backyard - Stylish Comfort Retreat

house - Chicago
This three-bedroom flat in Chicago's Near West Side is a 10-minute walk from the United Center, a 4-minute drive from the Illinois Medical District, and a 6-minute drive from the University of Illinois Chicago.
This professionally managed property offers 140 square metres of living space for up to six guests, featuring a fully equipped kitchen, high-speed Wi-Fi, Smart TVs, a washer/dryer, and a deck with a garden.
Luxury Home Theatre And Rooftop Oasis - Exquisite Architectural Masterpiece - Chicago, IL
Chicago, IL
2 5
£649/nighttotal: £4543 (7 )

Luxury Home Theatre And Rooftop Oasis - Exquisite Architectural Masterpiece

house - Chicago
This substantial five-bedroom residence is located in Chicago's Wicker Park/Bucktown districts, offering direct access to the Damen and Division Blue Line 'L' train stations, facilitating travel to the city centre.
This 418-square-metre property accommodates up to 17 guests and features a private 140-square-metre rooftop terrace with city views, a Clive Christian kitchen with Sub-Zero and Wolf appliances, a home cinema, a games room with a pool table and ping pong, a sauna, and a hot tub.
Casa Wolfram 20 Minutes From Downtown - Chicago, IL
10 26 reviews
Chicago, IL
4 2
£379/nighttotal: £1895 (5 )

Casa Wolfram 20 Minutes From Downtown

house - Chicago
This two-bedroom Chicago apartment is situated in Logan Square, offering convenient access to the Blue Line 'L' train and numerous amenities.
The 5-guest property features a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, free on-street parking, and a fitness centre; nearby attractions include award-winning restaurants and bars.
A Bit Of The North Woods On Chicago's North Side! - Chicago, IL
9.9 151 reviews
Chicago, IL
2 1
£183/nighttotal: £549 (3 )

A Bit Of The North Woods On Chicago's North Side!

house - Chicago
This renovated livery barn is situated in Rogers Park, a short walk from the Metra and Red Line, offering easy access to downtown Chicago. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The one-bedroom dwelling comfortably accommodates up to three guests and is equipped with a full kitchen, dining area, and two bathrooms. Guests can enjoy a private deck overlooking a garden and waterfall, a screen-free environment, and a Swedish design aesthetic, perfect for a quiet retreat or focused work.

Frequently asked questions about villa rentals in Chicago, IL

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Best Chicago, IL villas and holiday homes with a garden

74 M² House ∙ 2 Bedrooms ∙ 4 Guests - Chicago, IL
Chicago, IL
2 2
£108/nighttotal: £6588 (61 )

74 M² House ∙ 2 Bedrooms ∙ 4 Guests

house - Forest Park
Holiday house to rent for 4 guests. This accommodation is located in Forest Park.
Facilities and services include free parking, air conditioning and a washing machine. Pets are allowed in this house.
5 Bedroom Huge House In Best Location Parking Fireplace Back Yard - Chicago, IL
9.6 281 reviews
Chicago, IL
2 5
£482/nighttotal: £1928 (4 )

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

house - 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.
𓃥Wicker Cozy Corner W/parking On Site - Chicago, IL
10 149 reviews
Chicago, IL
3 2
£188/nighttotal: £752 (4 )

𓃥Wicker Cozy Corner W/parking On Site

house - Chicago
This Wicker Park house, a five-minute walk from the Damen Blue Line station, offers easy access to Chicago's attractions.
The two-bedroom, two-bathroom property sleeps six, boasting a fully equipped kitchen, private patio, high-speed internet, and Tesla EV charging; nearby amenities include numerous shops, restaurants, and bars.
Spacious Roscoe Village Getaway - Chicago, IL
9.8 8 reviews
Chicago, IL
2 3
£293/nighttotal: £2051 (7 )

Spacious Roscoe Village Getaway

house - Chicago
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.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL villas and holiday homes with parking

1 Mi To Washington Park: Spacious 1st-floor Condo! - Chicago, IL
Chicago, IL
1 2
£189/nighttotal: £378 (2 )

1 Mi To Washington Park: Spacious 1st-floor Condo!

house - Chicago
This ground-floor flat is situated in Chicago, 1.6 kilometres from Washington Park and 3.4 kilometres from the Museum of Science and Industry, offering convenient access to local attractions.
This apartment accommodates up to seven guests with two bedrooms and two bathrooms, featuring air conditioning, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, plus complimentary WiFi and private parking.
Beverly Hills Of Chicago Luxury Guest Favorite - Chicago, IL
9.9 41 reviews
Chicago, IL
10 5
£792/nighttotal: £2376 (3 )

Beverly Hills Of Chicago Luxury Guest Favorite

bungalow - Chicago
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.
Luxury 4br 4-story Chicago Villa Prime Gold Coast - Chicago, IL
Chicago, IL
4 4
£501/nighttotal: £2004 (4 )

Luxury 4br 4-story Chicago Villa Prime Gold Coast

house - Chicago
This four-storey townhome is situated in Chicago's historic Gold Coast, a short walk from Oak Street Beach, the Magnificent Mile, and numerous dining and entertainment venues.
This family-friendly property offers accommodation for 12 guests with four bedrooms, each featuring an ensuite bathroom, a fully equipped kitchen, free garage parking, and a private garden with a grill.
2 Newly Built Luxury Condos With Private Roofdeck - Chicago, IL
5.0 1 review
Chicago, IL
2 1
£1027/nighttotal: £18486 (18 )

2 Newly Built Luxury Condos With Private Roofdeck

house - Chicago
This newly built luxury condominium is situated in Chicago's Magnificent Mile, a short walk from Oak Street Beach and the Museum of Contemporary Art, and 1.8 kilometres from The Shops at Northbridge.
This spacious 5-bedroom residence offers 167 square metres of floor area, accommodating up to 16 guests with air conditioning, a fully equipped kitchen including a dishwasher and microwave oven, Wi-Fi, and a private roofdeck with outdoor seating, though bachelor(ette) parties are not permitted.

Find the Best Holiday Homes with a Pool in Chicago, IL

Enjoy a swim whenever you like, as these holiday homes in Chicago, IL feature excellent on-site pool facilities.

Extended Stay: Walk To Uic Campus & Train! - Chicago, IL
Chicago, IL
2 2
£323/nighttotal: £10336 (32 )

Extended Stay: Walk To Uic Campus & Train!

house - Chicago
Stylish Escape With Spacious Living Area And Modern Comforts - Chic Retreat - Chicago, IL
Chicago, IL
11 5
£799/nighttotal: £2397 (3 )

Stylish Escape With Spacious Living Area And Modern Comforts - Chic Retreat

house - Chicago
Forest Park Oasis - Dog Friendly - Parks - The "L" - Chicago, IL
9.9 31 reviews
Chicago, IL
4 2
£453/nighttotal: £906 (2 )

Forest Park Oasis - Dog Friendly - Parks - The "L"

house - Forest Park

Handpicked 5-Star Holiday Houses in Chicago, IL

Upscale holiday homes in Chicago, IL offer a memorable stay with premium amenities designed for those who appreciate the finer things.

139 M² House ∙ 3 Bedrooms ∙ 6 Guests - Chicago, IL
Chicago, IL
2 3
£502/nighttotal: £30622 (61 )

139 M² House ∙ 3 Bedrooms ∙ 6 Guests

house - Westchester

Check Out Holiday Houses with a Jacuzzi in Chicago, IL

Soothe your muscles in a holiday home's private hot tub after a busy city day; it is the perfect finishing touch to your Chicago, IL break.

Rooftop Deck And Heated Garage - Spectacular Urban Retreat - Chicago, IL
Chicago, IL
5 4
£1726/nighttotal: £3452 (2 )

Rooftop Deck And Heated Garage - Spectacular Urban Retreat

house - Chicago
Huge! 3br Private Home+garage+360° Roof Deck+hot Tub+ev+sleeps 12 - Chicago, IL
9.8 20 reviews
Chicago, IL
5 3
£696/nighttotal: £4176 (6 )

Huge! 3br Private Home+garage+360° Roof Deck+hot Tub+ev+sleeps 12

house - Chicago
Casa Brookfield | 5br + Hot Tub | Sleeps 14 - Chicago, IL
9.5 22 reviews
Chicago, IL
10 5
£379/nighttotal: £1137 (3 )

Casa Brookfield | 5br + Hot Tub | Sleeps 14

house - Brookfield
Stylish Rooftops And Sauna - Chic Urban Oasis - Chicago, IL
Chicago, IL
6 5
£436/nighttotal: £1744 (4 )

Stylish Rooftops And Sauna - Chic Urban Oasis

house - Chicago
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