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The 10 Best Villas in Chicago, USA

Check out our selection of great villas in Chicago

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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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.

I liked that the house felt like a home.

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9.4
Wonderful
123 reviews
Price from
$238.80
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
Wonderful
15 reviews
Price from
$357.37
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 complimentary WiFi and private parking available on site. The property is non-smoking and is situated 6.4 km from Union Station.

Very clean had everything we needed.

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9.3
Wonderful
6 reviews
Price from
$265.50
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.

It was calm, nice and equipped of everything needed. Ivan the host made everything to let us enjoy Chicago, he’s been awesome

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9.8
Exceptional
20 reviews
Price from
$269.51
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.

We loved the amount of space and how it accommodate 7 adults and 10 kids comfortably.

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9.8
Exceptional
5 reviews
Price from
$296.50
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 3 bedroom in Best Location Parking Fireplace Patio Home office 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
22 reviews
Price from
$279
per night

The spacious holiday home comes with 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 featured in the holiday home. For added privacy, the accommodation features a private entrance.

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Price from
$59
per night

Located within the Near North Side district in Chicago, Downtown Penthouse with Private Rooftop #2S has air conditioning, a patio, and city views. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is non-smoking and is set 1.7 km from Oak Street Beach.

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Price from
$45.50
per night

Boasting air-conditioned accommodation with a patio, The Orleans - Entire Building - With Rooftop Deck 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 1.7 km from Oak Street Beach.

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Price from
$1,499
per night

Set in Chicago, 1.6 km from Oak Street Beach and 2.4 km from Ohio Street Beach, Best location downtown - River North near MagMile offers air conditioning. Both free WiFi and parking on-site are available at the holiday home free of charge. The property is non-smoking and is located 2.7 km from North Avenue Beach.

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Price from
$129
per night

Looking for a villa?

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

  • The Avondale Guesthouse
    Breakfast options

    The Avondale Guesthouse is a recently renovated vacation home in Chicago where guests can make the most of the garden and barbecue facilities.

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

    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 123 reviews
  • Romantic 3 Bed Home In The Heart Of The Park
    Breakfast options

    Romantic 3 Bed Home In The Heart Of The Park is located in Chicago, just 2.3 miles from Museum of Science and Industry - Chicago and 3.8 miles from Guaranteed Rate Field.

    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 15 reviews
  • Spacious Row Home next Transit near Downtown w Parking
    Breakfast options

    Spacious Row Home next Transit near Downtown w Parking offers accommodations in Chicago, 2 miles from United Center and 4 miles from Union Station.

    Everything was clean and comfortable for 5 adults and 11 kids

    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 6 reviews
  • Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
    Breakfast options

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

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

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

    Offering a garden, Spacious 5-BR House near Transit w Parking offers accommodations in Chicago. 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

    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews
  • 3 bedroom in Best Location Parking Fireplace Patio Home office Pets Welcome
    Breakfast options

    Featuring a garden and inner courtyard views, this sustainable 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.

    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 22 reviews
  • Beautifully Remodeled Flat Downtown #3N
    Breakfast options

    Beautifully Remodeled Flat Downtown #3N is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.7 miles from North Avenue Beach.

  • Downtown Penthouse with Private Rooftop #2S
    Breakfast options

    Downtown Penthouse with Private Rooftop #2S offers accommodations in Chicago, 1.5 miles from Ohio Street Beach and 1.7 miles from North Avenue Beach.

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

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

FAQ about villas in Chicago



Villas That Guests Love in Chicago

  • Avg. price/night: $202.05
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 597 reviews
    Clean, nice & luxury
    Rafael
    Solo traveler
  • Avg. price/night: $241.86
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 2,680 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: $248.36
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 65 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: $430.95
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 323 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: $204.48
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 555 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 traveler
  • Avg. price/night: $557.65
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 1,199 reviews
    Luxury, fantastic view, nice gym
    Gabriel
    Young couple
  • Avg. price/night: $251.96
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 949 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
  • 7.2
    Scored 7.2
    Good
    Rated good
     · 900 reviews
    Location, close to the Loop and in the middle of the Hellenic village
    Josue
    Solo traveler
  • Avg. price/night: $198.58
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 2,207 reviews
    very luxurious and comfortable
    Justyna
    Young couple
  • Avg. price/night: $394.07
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 1,592 reviews
    Great value, excellent location and luxurious rooms. Room was so nice. The TV was great with built in Chromecast and the most comfortable bed I’ve ever slept in. A nice bottle of wine and a small box of chocolates was left for us on arrival - a really nice touch. The lighting controls in the room are great and the bathroom was fabulous - great shower and huge bathtub. The staff went above and beyond to welcome us also, I honestly couldn’t recommend the Viceroy enough, pure quality.
    Declan
    Young couple

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