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The 10 Best Villas in Chicago, USA

Check out our pick of great villas in Chicago

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Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

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Located in Chicago, 4.6 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi. This recently renovated holiday home is located 7.2 km from United Center and 8.1 km from 360 Chicago. On clear days, guests can head outside to enjoy the holiday home's outdoor fireplace or simply kick back and relax.

Everything was clean , working, and each detail to make your stay more cozy was provided

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9.3
Superb
122 reviews
Price from
£417
per night

Boasting air-conditioned accommodation with a patio, Stunning Condo #2 - Downtown River North is situated in Chicago. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is located 1.9 km from Oak Street Beach.

The location, the amount of bathrooms and bedrooms

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9.8
Exceptional
5 reviews
Price from
£238
per night

The 3-bedroom holiday home features 2 living rooms with a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the holiday home. The accommodation offers a fireplace.

The property had a lot of space and the host was a good host.

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9.1
Superb
16 reviews
Price from
£518
per night

Located in Chicago in the Illinois region, Spacious Row Home next Transit near Downtown w Parking features a patio. The air-conditioned accommodation is 3.2 km from United Center, and guests can benefit from on-site private parking and complimentary WiFi. The property is non-smoking and is situated 6.4 km from Union Station.

Very clean had everything we needed.

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9.4
Superb
7 reviews
Price from
£406
per night

Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find is a recently renovated holiday home in Chicago, where guests can make the most of its garden and tennis court. The air-conditioned accommodation is 5.7 km from Loyola University Chicago. There is an outdoor fireplace and guests can make use of free WiFi, free private parking and an electric vehicle charging station.

The property was super clean and had a very good vibe altogether.

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9.8
Exceptional
22 reviews
Price from
£305
per night

The spacious holiday home has 5 bedrooms, a flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a walk-in shower. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area.

Plenty of room. Very spacious.

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9.8
Exceptional
6 reviews
Price from
£497
per night

Boasting air-conditioned accommodation with a patio, Breathtaking Downtown Penthouse A - Sleeps 11 is set in Chicago. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is located 1.9 km from Oak Street Beach.

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8
Very good
5 reviews
Price from
£253
per night

The spacious holiday home has 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance.

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8
Very good
6 reviews
Price from
£167
per night

Set in Chicago, 1.8 km from United Center and 5 km from Union Station, Chic Green l Near Downtown & IL Medical District offers air conditioning. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is situated 5.2 km from Willis Tower.

Very clean and cute decorations!

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8.5
Very good
6 reviews
Price from
£238
per night

360 Chicago is 2 km from the holiday home, while Water Tower Chicago is 2.2 km away. The nearest airport is Midway International Airport, 20 km from Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome.

This was our first attempt at a non-hotel location. I was surprised how much we appreciated the home's amenities away from home. Amenities like; multiple bathrooms, full kitchen, private off-street parking and a pleasant neighborhood.

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8.5
Very good
23 reviews
Price from
£374
per night

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Perfect for families, groups or couples who enjoy luxury and independence while travelling. Enjoy the space and privacy of these fully-furnished, self-standing mansions — travellers can cook, lounge and explore at their leisure. Note that in Bali, a resort will also be called a villa.
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Enjoy breakfast in Chicago!

  • Stunning Condo #2 - Downtown River North
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Boasting air-conditioned accommodation with a patio, Stunning Condo #2 - Downtown River North is situated in Chicago.

    The location, the amount of bathrooms and bedrooms

  • Romantic 3 Bed Home In The Heart Of The Park
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 16 reviews

    Situated 6.2 km from Guaranteed Rate Field, 11 km from Art Institute of Chicago and 11 km from Field Museum of Natural History, Romantic 3 Bed Home In The Heart Of The Park features accommodation...

  • Spacious Row Home next Transit near Downtown w Parking
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 7 reviews

    Located in Chicago in the Illinois region, Spacious Row Home next Transit near Downtown w Parking features a patio.

    Everything was clean and comfortable for 5 adults and 11 kids

  • Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 22 reviews

    Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find is a recently renovated holiday home in Chicago, where guests can make the most of its garden and tennis court.

    The place is in a very cute neighborhood and was super clean.

  • Spacious 5-BR House near Transit w Parking
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 6 reviews

    Located in Chicago in the Illinois region, Spacious 5-BR House near Transit w Parking features a balcony. This property offers access to a terrace, free private parking and free WiFi.

    I came for my son’s birthday and he loved it very spacious and great communication

  • Breathtaking Downtown Penthouse A - Sleeps 11
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 5 reviews

    Boasting air-conditioned accommodation with a patio, Breathtaking Downtown Penthouse A - Sleeps 11 is set in Chicago.

  • Central Chicago Suite2 Access to Patio
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 6 reviews

    Situated in Chicago, 2.8 km from Water Tower Chicago and 2.9 km from United Center, Central Chicago Suite2 Access to Patio features air-conditioned accommodation with a patio and free WiFi.

  • Chicago Vacation Rental, 19 Mi to Downtown Area!

    Situated in Chicago, 19 km from Museum of Science and Industry - Chicago and 23 km from Guaranteed Rate Field, Chicago Vacation Rental, 19 Mi to Downtown Area! offers air conditioning.

Great access to the city centre! Check these villas in Chicago

  • Downtown Penthouse with Private Rooftop #2S
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located within the Near North Side district in Chicago, Downtown Penthouse with Private Rooftop #2S has air conditioning, a patio, and city views.

  • Brownstone in Gold Coast - Downtown
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located in the centre of Chicago, 600 metres from Oak Street Beach and 1.6 km from North Avenue Beach, Brownstone in Gold Coast - Downtown offers free WiFi and air conditioning.

  • Gold coast villa with free parking garage sleeps 10
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    In the centre of Chicago, located within a short distance of Oak Street Beach and North Avenue Beach, Gold coast villa with free parking garage sleeps 10 offers free WiFi, air conditioning and...

  • Beautiful Remodeled Penthouse Unit in Old Town
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located in Chicago, 1.7 km from Oak Street Beach and 1.9 km from Fullerton Beach, Beautiful Remodeled Penthouse Unit in Old Town offers air conditioning.

  • Stunning 2 Floor Penthouse Downtown
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 3 reviews

    Featuring air-conditioned accommodation with a patio, Stunning 2 Floor Penthouse Downtown is located in Chicago. Both free WiFi and parking on-site are available at the holiday home free of charge.

  • Immaculate Brand New Penthouse Chicago
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Situated in Chicago, 600 metres from United Center and 2.8 km from Union Station, Immaculate Brand New Penthouse Chicago offers air conditioning.

  • The Village Inn by Dakota Gal Digs
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 2 reviews

    Featuring air-conditioned accommodation with a patio, The Village Inn by Dakota Gal Digs is set in Chicago. Both free WiFi and parking on-site are available at the holiday home free of charge.

  • River North Hideaway with Amazing Views and Parking
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 3 reviews

    In a central area of Chicago, located within a short distance of Oak Street Beach and Ohio Street Beach, River North Hideaway with Amazing Views and Parking offers free WiFi, air conditioning and...

  • Luxurious classic Gold coast villa for 12 guests
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    In the heart of Chicago, set within a short distance of Oak Street Beach and North Avenue Beach, Luxurious classic Gold coast villa for 12 guests offers free WiFi, air conditioning and household...

  • 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 4 reviews

    Boasting a patio with city views, a garden and barbecue facilities, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome can be found in Chicago, close to Oak Street Beach...

  • The Avondale Guesthouse
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 122 reviews

    Located in Chicago, 4.6 km from Wrigley Field and 5.5 km from Lincoln Park Zoo, The Avondale Guesthouse provides air-conditioned accommodation with a patio and free WiFi.

    i like the games,couches and smart tv with good inter

  • Breathtaking Downtown Penthouse B - Sleeps 11
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Featuring air-conditioned accommodation with a patio, Breathtaking Downtown Penthouse B - Sleeps 11 is set in Chicago.

  • Beautiful 5br home for 14 guests with free parking
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 2 reviews

    Featuring city views, Beautiful 5br home for 14 guests with free parking offers accommodation with a patio, around 2 km from Oak Street Beach.

  • Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 23 reviews

    Featuring a garden and inner courtyard views, this holiday home is well located in Chicago, close to landmarks like North Avenue Beach and Lincoln Park Zoo.

    The location is excellent. Great for a group. Garage parking. Clean.

  • Chic Green l Near Downtown & IL Medical District
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 6 reviews

    Set in Chicago, 1.8 km from United Center and 5 km from Union Station, Chic Green l Near Downtown & IL Medical District offers air conditioning.

  • Historic luxury Townhouse in Downtown Chicago
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 4 reviews

    Right in the centre of Chicago, situated within a short distance of Oak Street Beach and Ohio Street Beach, Historic luxury Townhouse in Downtown Chicago offers free WiFi, air conditioning and...

  • Luxurious Gold Coast villa with parking for up to 12 guests
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 2 reviews

    Right in the heart of Chicago, Luxurious Gold Coast villa with parking for up to 12 guests has garden views from the balcony. This property offers access to a terrace and free private parking.

  • A terrific house for a large group.
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 4 reviews

    Set in Chicago, 11 km from Wrigley Field and 14 km from Lincoln Park Zoo, A terrific house for a large group. Offers air-conditioned accommodation with a terrace and free WiFi.

  • Beautifully Remodeled Flat Downtown #3N
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1 review

    Set in Chicago, 2.4 km from Ohio Street Beach and 2.7 km from North Avenue Beach, Beautifully Remodeled Flat Downtown #3N offers air conditioning.

  • 5 Bedroom House in Best Location Parking Fireplace Back Yard Home office
    7.5
    Scored 7.5
    Good
    Rated good
     · 2 reviews

    Featuring a patio with city views, a garden and barbecue facilities, 5 Bedroom House in Best Location Parking Fireplace Back Yard Home office can be found in Chicago, close to North Avenue Beach and...

  • Best location downtown - River North near Mag Mile
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    Featuring air-conditioned accommodation with a patio, Best location downtown - River North near Mag Mile is located in Chicago.

  • The Black And White Suite
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    The Black And White Suite is situated in the Bronzeville district of Chicago, 3.2 km from Guaranteed Rate Field, 5.4 km from Museum of Science and Industry - Chicago and 6.3 km from Field Museum of...

  • Chicago Big House
    Central location

    Set in Chicago in the Illinois region, Chicago Big House has a terrace and garden views. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • 2 Newly Built Luxury Condos with Private Roofdeck

    Featuring air-conditioned accommodation with a patio, 2 Newly Built Luxury Condos with Private Roofdeck is located in Chicago.

  • New Construction Building in River North

    Boasting air-conditioned accommodation with a patio, New Construction Building in River North is set in Chicago. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Stunning Duplex Condo #1 - Downtown River North

    Boasting air-conditioned accommodation with a patio, Stunning Duplex Condo #1 - Downtown River North is situated in Chicago.

  • 2 Newly Built Luxury Condos with Private Roofdeck

    Boasting air-conditioned accommodation with a patio, 2 Newly Built Luxury Condos with Private Roofdeck is situated in Chicago.

  • The Orleans - Floor 2 Private roof deck Patio

    Featuring air-conditioned accommodation with a patio, The Orleans - Floor 2 Private roof deck Patio is set in Chicago.

Travelling by car? These villas in Chicago offer free parking!

FAQ about villas in Chicago



Villas that guests love in Chicago

  • Avg. price/night: £226.45
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 2,817 reviews
    The view from my room was amazing. The room was super comfortable and very modern. The hotel decor felt very luxurious and shared spaces were comfortable. The food was good.
    Brenda
    Group
  • Avg. price/night: £284.70
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1,450 reviews
    The waterfront view was so captivating that I couldn't contain my excitement when I checked in to the hotel. Top-quality luxury and attention to details, with an additional corner sofa banquet, was definitely my favorite spot in the room. I had a convention over the weekend and it was easy to walk from the hotel to the festival hall, which had a lot of food and retail shops.
    Priscilla Jennifer
    Family with young children
  • Avg. price/night: £234.23
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 618 reviews
    Clean, nice & luxury
    Rafael
    Solo traveller
  • Avg. price/night: £226.45
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 2,817 reviews
    Every one was happy and very nice ..the environment was very clean and classy I love the breakfast and I love that the bar stays open 24 hours they barbecue Pizza was a plus 10 overall everything was beautiful it gave me like a dorm/hotel/ luxury lol
    Gainous
    Young couple
  • Avg. price/night: £308.52
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 62 reviews
    Rosa & Edith were attentive to our needs and expectations. The entire staff was friendly, accommodating and engaging. The Villa was at our disposal, and we were able to enjoy the amenities with our daughter and her husband who live nearby.
    Nosal
    Young couple
  • Avg. price/night: £576.06
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1,579 reviews
    My parents and I had the most wonderful stay at the Viceroy earlier this month. The facilities and hotel amenities are top class and the whole hotel has a really luxurious feel. Despite not staying in one of the larger offerings, we found the Deluxe Queen room to be very spacious. A special thanks to the hotel staff who always greeted us warmly and went above and beyond to make our stay comfortable! The surrounding area is great as well- lots of restaurants and shops!
    Simone
    Family with young children
  • Avg. price/night: £472.59
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 339 reviews
    Very stylish hotel - I loved the cool and comfy chairs and sofas in the room and public spaces. The room was cleverly laid out to be compact but still felt luxurious. I also liked the Nespresso machine and the refillable water instead of having water bottles. The hotel is in a great location for the el and Amtrak which is exactly what we wanted.
    Julie
    Young couple
  • Avg. price/night: £224.57
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 560 reviews
    The room was spacious, the sheets and pillows on the bed were extremely soft and luxurious; the staff was friendly and the hotel lobby and library was inviting.
    Rhomance
    Solo traveller
  • Avg. price/night: £491.23
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 1,224 reviews
    Luxury, fantastic view, nice gym
    Gabriel
    Young couple
  • Avg. price/night: £240.57
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 951 reviews
    Imposing building with high quality feel and relaxing ambiance. The room was large, luxurious and in pristine condition with top quality bed, bedding and sofa. Location is fabulous for a first-time visitor. Even though the room overlooked the L Train, the sound deadening was excellent
    Andrew
    Young couple

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