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The best villas in Chicago

Check out our selection of great villas in Chicago

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The Avondale Guesthouse, hotel in Chicago

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

Great location, and the place was super clean! We really enjoyed our short stay here.
Scored 9.3
9.3
Rated wonderful
Wonderful
143 reviews
Price from
$204.18
1 night, 2 adults
Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub, hotel in Chicago

A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.

Everything was fantastic!
Scored 9.6
9.6
Rated exceptional
Exceptional
7 reviews
Price from
$400
1 night, 2 adults
A terrific house for a large group., hotel in Chicago

A terrific house for a large group. Is located in Chicago, just 7 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo.

One thing we all really enjoyed was how everyone’s bedroom was somewhat close to one another as well as how the living room was big enough to do different types of games and such
Scored 8.8
8.8
Rated excellent
Excellent
6 reviews
Price from
$245.09
1 night, 2 adults
A Home Away from Home!, hotel in Chicago

A Home Away from Home! is located in Chicago, just 4.4 miles from Museum of Science and Industry - Chicago and 9.5 miles from Guaranteed Rate Field.

Scored 6.4
6.4
Rated pleasant
Pleasant
5 reviews
Price from
$203.70
1 night, 2 adults
Chic Green l Near Downtown & IL Medical District, hotel in Chicago

Chic Green l Near Downtown & IL Medical District offers accommodations in Chicago, 3.1 miles from Union Station and 3.2 miles from Willis Tower.

Very responsive host. When we had issues entering the unit at checkin they were able to remotely unlock until the issue was resolved.
Scored 7.7
7.7
Rated good
Good
18 reviews
Price from
$126
1 night, 2 adults
4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome, hotel in Chicago

A 19-minute walk from Oak Street Beach in Chicago, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome provides accommodations with access to spa facilities and fitness...

Scored 9.6
9.6
Rated exceptional
Exceptional
5 reviews
Lincoln Park Living - Suite 1, hotel in Chicago

Lincoln Park Living - Suite 1 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

Very Clean
Scored 9.4
9.4
Rated wonderful
Wonderful
17 reviews
The Black And White Suite, hotel in Chicago

The Black And White Suite is located in Chicago, just 4.3 miles from Adler Planetarium & Astronomy Museum and 4.6 miles from Art Institute of Chicago.

It's like walking into art and everything we could have wanted for our first visit to Chicago. For jazz and blues fans, the area is perfect! Quick access to public transit and walking distance from many things.
Scored 9.0
9.0
Rated wonderful
Wonderful
6 reviews
Stunning Condo #2 - Downtown River North, hotel in Chicago

Stunning Condo #2 - Downtown River North is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

3 rooms Garage Roku Heated floor in master bathroom Balcony would be really nice during the summer.
Scored 9.2
9.2
Rated wonderful
Wonderful
21 reviews
Stunning 2 Floor Penthouse Downtown, hotel in Chicago

Stunning 2 Floor Penthouse Downtown is located in Chicago, just 1.9 miles from Water Tower Chicago and 1.9 miles from United Center.

Close to shops and subway - great location on a quiet street. We will be back. Lots of room, and kids really enjoyed the decks. Parking spot was also appreciated. Thank you!
Scored 9.2
9.2
Rated wonderful
Wonderful
13 reviews
All villas in Chicago
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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.

Most booked villas in Chicago and surrounding area in the past month

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Enjoy breakfast in Chicago!

  • Lincoln Park Living - Suite 1
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 17 reviews

    Lincoln Park Living - Suite 1 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

    Location, spacious, lots of beds, big kitchen, free street parking.

  • Stunning Condo #2 - Downtown River North
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 21 reviews

    Stunning Condo #2 - Downtown River North is located in Chicago, just 1.5 miles from Ohio Street Beach and 1.8 miles from North Avenue Beach.

    The location, the amount of bathrooms and bedrooms

  • Stunning 2 Floor Penthouse Downtown
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 13 reviews

    Stunning 2 Floor Penthouse Downtown is located in Chicago, just 1.9 miles from Water Tower Chicago and 1.9 miles from United Center.

    It was very spacious! I enjoyed the view from the private balcony.

  • Beautifully Renovated House 10 mins from Downtown
    Scored 9.4
    9.4
    Rated wonderful
    Wonderful
     · 5 reviews

    Beautifully Renovated House 10 mins from Downtown offers accommodations in Chicago, 1.5 miles from Oakwood Beach and 1.8 miles from Guaranteed Rate Field.

    Excellent location, beautiful, clean and spacious house with all amenities needed. Fantastic communication and friendly service, would love to stay here again.

  • Spacious Luxury Retreat 8 Bed Oasis with 6 Baths
    Scored 9.2
    9.2
    Rated wonderful
    Wonderful
     · 5 reviews

    Spacious Luxury Retreat 8 Bed Oasis with 6 Baths offers accommodations in Chicago, 2.4 miles from Guaranteed Rate Field and 3.1 miles from Union Station.

  • Spacious Row Home next Transit near Downtown w Parking
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 11 reviews

    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

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

    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.

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

    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.

    Excellent, it was close to downtown and the airport.

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

  • Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Cozy 4bd House Fireplace and Pond is located in Chicago, just 9.4 miles from Guaranteed Rate Field and 10 miles from Field Museum of Natural History.

  • Historic luxury Townhouse in Downtown Chicago
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 3 reviews

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 8-minute walk from Water Tower Chicago and half a mile from Chicago Museum of Contemporary Art.

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

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Gold coast villa with free parking garage sleeps 10 features accommodations in Chicago with a garden.

  • Modern SFH Near McCormick Place & Soldier Field
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Modern SFH Near McCormick Place & Soldier Field is located in Chicago, just 1.8 miles from Union Station and 1.8 miles from Willis Tower.

  • Old Town Pied-a-Terre with Private Terrace and Parking!
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    A 14-minute walk from North Avenue Beach in Chicago, Old Town Pied-a-Terre with Private Terrace and Parking! offers accommodations with access to a hot tub.

  • Luxury Retreat with Home Theater
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Luxury Retreat with Home Theater offers accommodations in Chicago, 2.2 miles from United Center and 2.5 miles from Lincoln Park Zoo.

  • Chicago Mid-Century Gem By United Center
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Chicago Mid-Century Gem By United Center offers accommodations in Chicago, a 8-minute walk from United Center and 2.6 miles from Union Station.

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

    The Village Inn by Dakota Gal Digs is located in Chicago, just 1.8 miles from Fullerton Beach and 1.8 miles from North Avenue Beach.

  • Hamaline Luxury & Tranquil Home
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Hamaline Luxury & Tranquil Home is located in Chicago, just a 17-minute walk from Guaranteed Rate Field and 3.7 miles from Art Institute of Chicago.

  • ENTIRE BUILDING-Walk to Lincoln Park or The Beach
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    ENTIRE BUILDING-Walk to Lincoln Park or The Beach offers accommodations in Chicago, 1.9 miles from North Avenue Beach and 1.2 miles from Wrigley Field.

  • The Logandale: HUGE Mid-Century Home, sleeps 15
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 4 reviews

    The Logandale: HUGE Mid-Century Home, sleeps 15 offers accommodations in Chicago, 4.6 miles from Lincoln Park Zoo and 5.1 miles from United Center.

  • Stylish Chicago Retreat Walk to Loyola University
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Stylish Chicago Retreat Walk to Loyola University is located in Chicago, just a 8-minute walk from Loyola University Chicago and 3.5 miles from Wrigley Field.

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

    River North Hideaway with Amazing Views and Parking offers accommodations in Chicago, 1.6 miles from North Avenue Beach and a 11-minute walk from 360 Chicago.

  • 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 5 reviews

    A 19-minute walk from Oak Street Beach in Chicago, 4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome provides accommodations with access to spa facilities and fitness...

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

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Luxurious classic Gold coast villa for 12 guests features accommodations in Chicago with a garden.

  • Chicago Treasure 4 Bed Getaway
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 4 reviews

    Chicago Treasure 4 Bed Getaway offers accommodations in Chicago, 1.9 miles from Water Tower Chicago and 2 miles from Chicago Museum of Contemporary Art.

  • Windy City Getaway - 3BR 2BA Chicago Townhouse home
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 2 reviews

    Windy City Getaway - 3BR 2BA Chicago Townhouse home is located in Chicago, just 5 miles from Wrigley Field and 6.1 miles from Lincoln Park Zoo.

  • Chicago Home Near Navy Pier and Shedd Aquarium!
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 4 reviews

    Chicago Home Near Navy Pier and Shedd Aquarium! offers accommodations in Chicago, 8.4 miles from Guaranteed Rate Field and 11 miles from Field Museum of Natural History.

  • The Avondale Guesthouse
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 143 reviews

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

    The size of the apartment was large. Parking was free.

  • The Black And White Suite
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 6 reviews

    The Black And White Suite is located in Chicago, just 4.3 miles from Adler Planetarium & Astronomy Museum and 4.6 miles from Art Institute of Chicago.

    Casa muy amplia, cómoda , limpia barrio muy tranquilo

  • Luxurious Gold Coast villa with parking for up to 12 guests
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 3 reviews

    Just 1.1 miles from North Avenue Beach and a 12-minute walk from 360 Chicago, Luxurious Gold Coast villa with parking for up to 12 guests features accommodations in Chicago with a garden.

  • No. 1 Rated Lincoln Park House - Golf Simulator
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 1 review

    No. 1 Rated Lincoln Park House - Golf Simulator offers accommodations in Chicago, a 7-minute walk from Lincoln Park Zoo and 1.6 miles from 360 Chicago.

  • A terrific house for a large group.
    Scored 8.8
    8.8
    Rated excellent
    Excellent
     · 6 reviews

    A terrific house for a large group. Is located in Chicago, just 7 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo.

  • Beautiful Remodeled Penthouse Unit in Old Town
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 9 reviews

    Beautiful Remodeled Penthouse Unit in Old Town offers accommodations in Chicago, 1.4 miles from 360 Chicago and 1.4 miles from Water Tower Chicago.

  • Lincoln Park Living - 3 Queen Beds - Sleeps 6
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 10 reviews

    Lincoln Park Living - 3 Queen Beds - Sleeps 6 is located in Chicago, just 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

    Everything was wonderful could have used a few more pans for cooking like a skillet.

  • Chicago Home with Spacious Yard 14 Mi to Dtwn
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 9 reviews

    Chicago Home with Spacious Yard 14 Mi to Dtwn is located in Chicago, just 10 miles from Guaranteed Rate Field and 13 miles from Field Museum of Natural History.

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

    Just 1.1 miles from North Avenue Beach and a 16-minute walk from Lincoln Park Zoo, Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome features accommodations in...

    Breakfast was amazing, the 0lace is super and location is great, with free and efficient parking. Great service also

  • 5 Mi to Millennium Park Apartment with Fireplaces
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 2 reviews

    5 Mi to Millennium Park Apartment with Fireplaces offers accommodations in Chicago, 2.3 miles from United Center and 4.7 miles from Union Station.

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

  • Charming Home in Portage Park

    Charming Home in Portage Park is located in Chicago, just 10 miles from Loyola University Chicago and 10 miles from United Center. The air-conditioned accommodation is 9.2 miles from Lincoln Park Zoo.

  • Designer Smart Home

    Offering a fitness center and a garden, Designer Smart Home in Chicago is close to North Avenue Beach and Lincoln Park Zoo. The air-conditioned accommodation is a 13-minute walk from Oak Street Beach.

  • The Urban Manor

    The Urban Manor offers accommodations in Chicago, a 18-minute walk from Oakwood Beach and 2.5 miles from Guaranteed Rate Field.

  • Luxe 4BR with Hot Tub & Game Room
    Scored 8.3
    8.3
    Rated very good
    Very Good
     · 3 reviews

    Luxe 4BR with Hot Tub & Game Room offers accommodations in Chicago, 2.5 miles from Union Station and 2.6 miles from Shops at Northbridge.

  • Lakefront Rooftop Parking
    Scored 4.5
    4.5
    Rated disappointing
    Disappointing
     · 2 reviews

    Providing a garden, Lakefront Rooftop Parking features accommodations in Chicago. This beachfront property offers access to a patio, free private parking, and free Wifi.

  • Chic Green l Near Downtown & IL Medical District
    Scored 7.7
    7.7
    Rated good
    Good
     · 18 reviews

    Chic Green l Near Downtown & IL Medical District offers accommodations in Chicago, 3.1 miles from Union Station and 3.2 miles from Willis Tower.

    Die Wohnung ist wirklich schön eingerichtet, und war sehr sauber.

  • Lincoln Park Living - Suite 2
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 9 reviews

    Lincoln Park Living - Suite 2 offers accommodations in Chicago, 1.5 miles from Fullerton Beach and 1.9 miles from North Avenue Beach.

    Arrangement was done nicely and house supplies were enough for everyone

  • Suite 2 on Southport 4 Queen Beds
    Scored 8.4
    8.4
    Rated very good
    Very Good
     · 15 reviews

    Suite 2 on Southport 4 Queen Beds is located in Chicago, just 1.8 miles from Wrigley Field and 3.4 miles from 360 Chicago. The air-conditioned accommodation is 1.7 miles from Lincoln Park Zoo.

    Lokalizacja, standard apartamentu, wyposażenie lokalu

FAQ about villas in Chicago

Villas That Guests Love in Chicago

See all
  • Avg. price/night: $133.21
    Scored 7.6
    7.6
    Rated good
    Good
     · 6,931 reviews
    It was quite cool and luxurious, great location
    Deborah
    Group
  • Avg. price/night: $155.01
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 4,964 reviews
    Great location, great value, decent sized room with a nice bed and luxurious pillows. Rooms were quiet and curtains blocked the light effectively. The staff were excellent - I arrived at 10:30am to ask if I could leave my bags and I was checked in there and then!
    Stephen
    Solo traveler
  • Avg. price/night: $230.55
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 1,568 reviews
    The breakfast at the hotel restaurant was included in our booking and it was absolutely fantastic, the best breakfast we've ever had in a hotel! We tried something different for each of the 7 mornings we were there. I couldn't believe it was all included in the price of the booking. 5 star service! The location of the hotel was great and walking distance from every tourist attraction. The lobby and bar area felt really luxurious and welcoming.
    Sasha
    Young couple
  • Avg. price/night: $139.69
    Scored 7.3
    7.3
    Rated good
    Good
     · 6,512 reviews
    We stayed in Room 940 and it was nice. It wasn't a luxury suite, but it served us well.
    L
    Leslie
    Young couple
  • Avg. price/night: $171.50
    Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 1,017 reviews
    It was roomy, clean and luxurious
    scott
    Family with young children
  • Avg. price/night: $138.62
    Scored 6.4
    6.4
    Rated pleasant
    Pleasant
     · 232 reviews
    Im so happy i came across Villa Dubois Guesthouse. The whole property is clean and organized, free street parking, neighborhood is quiet. I love the full functional kitchen where you can prepare meals.security cameras around the common area for safety.If you dont mind sharing a space with strangers,this a nice budget friendly place to stay😊
    LIW-LIWA
    Young couple
  • Scored 8.0
    8.0
    Rated very good
    Very Good
     · 3 reviews
    Great, well maintained luxury apartment, very clean and in perfect location. Also very nice host. Perfect.
    Grace
    Family with young children
  • Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 33 reviews
    It's like a little courtyard villa in Montparnasse, with a wrought-iron balcony and birds singing in the garden. Great shower!
    Mary
    Solo traveler
  • Avg. price/night: $128.72
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 948 reviews
    The location was excellent for our travel plans. We were there to hear music at Buddy Guy's Legends and do some sight seeing during the day. The stadium tour of Wriggley Field was a high light. The Italian Village was a nice surprise with fantastic food. My partner is gluten free and the options they had were outstanding. The restaurant is a bit pricey.
    EJAYBICK
    Young couple
  • Avg. price/night: $463.73
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 165 reviews
    A stay at the Four Seasons is a luxurious experience, expensive but worth it. The facilities at the Chicago location offer an escape from the hustle and bustle of the busy downtown area. The (city) views from the south facing side of the building are amazing.
    Alexandra
    Young couple

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