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The best villas in Chicago

Check out our pick of great villas in Chicago

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The Avondale Guesthouse, hotel in Chicago

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

The location was perfect, it was also very clean and the owner was really very attentive, I would recommend it
Scored 9.3
9.3
Rated superb
Superb
143 reviews
Price from
£315.08
1 night, 2 adults
The Black And White Suite, hotel in Chicago

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...

Scored 9.0
9.0
Rated superb
Superb
6 reviews
Price from
£569.04
1 night, 2 adults
Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub, hotel in Chicago

A recently renovated holiday home situated in Chicago, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub features a garden.

Loved the location/neighborhood with proximity to the downtown area but privacy while spending time at the house. The size is great, outside property very nice. Plenty of street parking for folks who drive, but easy public transportation access for folks who use that to get in/around.
Scored 9.6
9.6
Rated exceptional
Exceptional
7 reviews
Price from
£478.14
1 night, 2 adults
A terrific house for a large group., hotel in Chicago

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.

Scored 8.8
8.8
Rated fabulous
Fabulous
6 reviews
Price from
£501.11
1 night, 2 adults
A Home Away from Home!, hotel in Chicago

Set 7 km from Museum of Science and Industry - Chicago, A Home Away from Home! offers accommodation with free WiFi and free private parking.

Scored 6.4
6.4
Rated pleasant
Pleasant
5 reviews
Price from
£381.10
1 night, 2 adults
Chic Green l Near Downtown & IL Medical District, hotel in Chicago

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.

Scored 7.7
7.7
Rated good
Good
18 reviews
Price from
£202.35
1 night, 2 adults
4 bedroom in Best Location Parking Fireplace Back Yard Home office Pets Welcome, hotel in Chicago

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...

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

Located in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - Suite 1 provides air-conditioned accommodation with a patio and free WiFi.

Just like the pictures! Everything was very clean, we had a great time
Scored 9.4
9.4
Rated superb
Superb
17 reviews
Stunning Condo #2 - Downtown River North, hotel in Chicago

Situated within the Near North Side district in Chicago, Stunning Condo #2 - Downtown River North has air conditioning, a patio, and city views.

Fantastic property very close to the downtown area of Chicago, near the metro and the bus stop. Beautifully done up interiors, Very spacious and can easily accommodate 12-14 people . Ample amount of coffee milk and sugar at disposal. Prompt replies from the owner for everything we needed.
Scored 9.2
9.2
Rated superb
Superb
22 reviews
Stunning 2 Floor Penthouse Downtown, hotel in Chicago

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.

Scored 9.2
9.2
Rated superb
Superb
13 reviews
All villas in Chicago
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Enjoy breakfast in Chicago!

  • Lincoln Park Living - Suite 1
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 17 reviews

    Located in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - Suite 1 provides air-conditioned accommodation with a patio and free WiFi.

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

  • Stunning Condo #2 - Downtown River North
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 22 reviews

    Situated within the Near North Side district in Chicago, Stunning Condo #2 - Downtown River North has air conditioning, a patio, and city views.

    The location, the amount of bathrooms and bedrooms

  • Stunning 2 Floor Penthouse Downtown
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 13 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.

    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 superb
    Superb
     · 5 reviews

    Located within the Bronzeville district in Chicago, Beautifully Renovated House 10 mins from Downtown has air conditioning, a balcony, and garden views.

    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 superb
    Superb
     · 5 reviews

    Situated within the Bridgeport district in Chicago, Spacious Luxury Retreat 8 Bed Oasis with 6 Baths has air conditioning, a patio, and city views.

  • Spacious Row Home next Transit near Downtown w Parking
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 11 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
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 36 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
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 11 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.

    Excellent, it was close to downtown and the airport.

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

  • Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set in Chicago, 6.8 km from Museum of Science and Industry - Chicago and 15 km from Guaranteed Rate Field, Cozy 4bd House Fireplace and Pond offers a garden and air conditioning.

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

  • Gold coast villa with free parking garage sleeps 10
    Scored 10.0
    10.0
    Rated exceptional
    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...

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

    Set in Chicago, 2.8 km from Union Station and 3 km from Willis Tower, Modern SFH Near McCormick Place & Soldier Field offers air-conditioned accommodation with a patio and free WiFi.

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

    Boasting air-conditioned accommodation with a patio, Old Town Pied-a-Terre with Private Terrace and Parking! is situated in Chicago. It is located 1.2 km from North Avenue Beach and features a lift.

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

    Set within the Wicker Park district in Chicago, Luxury Retreat with Home Theater has air conditioning, a patio, and city views.

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

    Boasting air-conditioned accommodation with a patio, Chicago Mid-Century Gem By United Center is situated in Chicago.

  • The Village Inn by Dakota Gal Digs
    Scored 10.0
    10.0
    Rated exceptional
    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.

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

    Located in Chicago, 1.4 km from Guaranteed Rate Field and 6 km from Art Institute of Chicago, Hamaline Luxury & Tranquil Home provides air-conditioned accommodation with a balcony and free WiFi.

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

    Situated in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, ENTIRE BUILDING-Walk to Lincoln Park or The Beach offers air conditioning.

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

    Situated in Chicago, 6.5 km from Wrigley Field and 7.4 km from Lincoln Park Zoo, The Logandale: HUGE Mid-Century Home, sleeps 15 offers air conditioning.

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

    Located in Chicago, 700 metres from Loyola University Chicago and 5.7 km from Wrigley Field, Stylish Chicago Retreat Walk to Loyola University offers air conditioning.

  • River North Hideaway with Amazing Views and Parking
    Scored 9.7
    9.7
    Rated exceptional
    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...

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

  • Luxurious classic Gold coast villa for 12 guests
    Scored 9.5
    9.5
    Rated exceptional
    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...

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

    Located in Chicago, 3 km from Water Tower Chicago and 3.3 km from Chicago Museum of Contemporary Art, Chicago Treasure 4 Bed Getaway offers air conditioning.

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

    Boasting air-conditioned accommodation with a patio, Windy City Getaway - 3BR 2BA Chicago Townhouse home is situated in Chicago. This property offers access to a balcony and free private parking.

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

    Located in Chicago, 9.3 km from Museum of Science and Industry - Chicago and 14 km from Guaranteed Rate Field, Chicago Home Near Navy Pier and Shedd Aquarium! offers air conditioning.

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

    The Avondale Guesthouse is a recently renovated holiday home in Chicago, where guests can make the most of its 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 superb
    Superb
     · 6 reviews

    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...

    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 superb
    Superb
     · 3 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.

  • No. 1 Rated Lincoln Park House - Golf Simulator
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 1 review

    Set in Chicago, 1.2 km from North Avenue Beach and 2 km from Fullerton Beach, No. 1 Rated Lincoln Park House - Golf Simulator offers air conditioning.

  • A terrific house for a large group.
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 6 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.

  • Beautiful Remodeled Penthouse Unit in Old Town
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 9 reviews

    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.

  • Lincoln Park Living - 3 Queen Beds - Sleeps 6
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 11 reviews

    Set in Chicago, 2.5 km from Fullerton Beach and 3 km from North Avenue Beach, Lincoln Park Living - 3 Queen Beds - Sleeps 6 offers air-conditioned accommodation with a patio and free WiFi.

    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 8.7
    8.7
    Rated fabulous
    Fabulous
     · 10 reviews

    Set in Chicago, 12 km from Museum of Science and Industry - Chicago and 16 km from Guaranteed Rate Field, Chicago Home with Spacious Yard 14 Mi to Dtwn offers air conditioning.

  • 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

    Featuring a patio with inner courtyard views, a garden and barbecue facilities, Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome can be found in Chicago, close to...

    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

    Located in Chicago, 3.8 km from United Center and 7.6 km from Union Station, 5 Mi to Millennium Park Apartment with Fireplaces provides air-conditioned accommodation with a balcony and free WiFi.

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

  • Tuscan Charm in Chicago's Heart

    Set in Chicago, 1.2 km from Wrigley Field and 4.8 km from Lincoln Park Zoo, Tuscan Charm in Chicago's Heart offers air conditioning.

  • Zen Escape-Chicago's Urban Oasis

    Situated in Chicago, 3.3 km from United Center and 6.1 km from Water Tower Chicago, Zen Escape-Chicago's Urban Oasis offers air conditioning.

  • Charming Home in Portage Park

    Set in Chicago, 15 km from Lincoln Park Zoo and 16 km from Loyola University Chicago, Charming Home in Portage Park offers air conditioning.

  • Designer Smart Home

    Set in Chicago, 1.1 km from Oak Street Beach and 1.2 km from North Avenue Beach, Designer Smart Home offers a garden and air conditioning.

  • The Urban Manor

    Boasting air-conditioned accommodation with a patio, The Urban Manor is set in Chicago. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

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

    Set in Chicago, 1.6 km from United Center and 4 km from Union Station, Luxe 4BR with Hot Tub & Game Room offers air conditioning.

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

    Boasting air-conditioned accommodation with a patio, Lakefront Rooftop Parking is situated in Chicago. This beachfront property offers access to a balcony, free private parking and free WiFi.

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

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

FAQ about villas in Chicago

Villas that guests love in Chicago

See all
  • Avg. price/night: £107.39
    Scored 7.6
    7.6
    Rated good
    Good
     · 6,927 reviews
    It was quite cool and luxurious, great location
    Deborah
    Group
  • Avg. price/night: £124.97
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 4,962 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 traveller
  • Avg. price/night: £185.86
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 1,566 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: £112.62
    Scored 7.3
    7.3
    Rated good
    Good
     · 6,514 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: £138.26
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 1,018 reviews
    It was roomy, clean and luxurious
    scott
    Family with young children
  • Avg. price/night: £114.67
    Scored 6.4
    6.4
    Rated pleasant
    Pleasant
     · 230 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 traveller
  • Avg. price/night: £103.77
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 946 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: £373.84
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 166 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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