The 10 best villas in Chicago, US

The best villas in Chicago

Check out our selection of great villas in Chicago

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The Avondale Guesthouse

Chicago

The Avondale Guesthouse is located in Chicago, just 2.8 miles from Wrigley Field and 3.6 miles from Lincoln Park Zoo.

K

Kam

From

United States

Easy access to a nice property in a good location. The hosts were amazing and easy to communicate with. Noemi was so nice and decorated the house for the holiday- it was so cool! We had a blast!

Scored out of 10, guest rating 9.6

Exceptional - What previous guests thought, 129 reviews

Price from

$340

1 night, 2 adults

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Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub

Chicago

Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub is located in Chicago, just 4.5 miles from Wrigley Field and 7.2 miles from Lincoln Park Zoo.

A

Ashley

From

United States

This is truly a home away from home. We felt at ease the entire stay and even though we had a jam-packed trip, coming back to the house felt like coming home. The neighborhood is great for walking, and feels extremely safe. There are fantastic coffee shops and restaurants all throughout the neighborhood, and the street parking is plentiful, which makes staying in the city so much easier. I had exactly 30 minutes to myself during the trip, and while everyone else rested, I got in the hot tub and really recharged for the rest of our evening. It was cool outside and perfect in the tub. I cannot more highly recommend this home, and I can't thank Andrea enough. The house is historic and beautiful, and very clean. The beds are so comfortable, and having more than one bathroom is such a bonus. We ended up needing to use the dryer, and it's so nice to have laundry facilities when you accidentally end up with a wet shoe and socks! There's a fireplace and seating for hanging out inside when it's chilly, and it's super cozy. There's a Keurig for coffee and Andrea even offered to get us milk for coffee, but we opted to walk down to the local spots and soak in the neighborhood. I've said a lot but I still feel like I'm not capturing how great the property really is. If you've found this one, stop scrolling!

Scored out of 10, guest rating 9.4

Wonderful - What previous guests thought, 8 reviews

Price from

$500

1 night, 2 adults

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Designer Themed 4 Bedroom in Best Location with Patio and Fireplace

Near North Side, Chicago

Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

S

Strand

From

United States

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.

Scored out of 10, guest rating 9.8

Exceptional - What previous guests thought, 20 reviews

Price from

$609

1 night, 2 adults

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Hamaline Luxury Guest House

Bronzeville, Chicago

Hamaline Luxury Guest House is located in Chicago, just 1.8 miles from Oakwood Beach and a 16-minute walk from Guaranteed Rate Field.

C

Clint

From

United States

Everything about this place and its surrounding area caters to your every need the perfect getaway from home...

Scored out of 10, guest rating 7.1

Good - What previous guests thought, 14 reviews

Price from

$321.44

1 night, 2 adults

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Lakefront Rooftop Parking

Chicago

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

D

Demetris

From

United States

Very nice, the owner was very helpful and on time with my needs, felt like home❤️

Scored out of 10, guest rating 7.5

Good - What previous guests thought, 11 reviews

Price from

$700.75

1 night, 2 adults

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Pearly Gates l 3 Bed l Sleeps 5 l w 2-Car Garage

Forest Park (Near Chicago)

Pearly Gates l 3 Bed l Sleeps 5 l w 2-Car Garage offers accommodations in Forest Park, 7.6 miles from United Center and 9.3 miles from Union Station.

J

Jessica

From

United States

Great neighborhood, no noise and very clean ! Would most definitely be back and recommend with my family , friends , etc .

Scored out of 10, guest rating 9.3

Wonderful - What previous guests thought, 14 reviews

Price from

$302

1 night, 2 adults

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Sleeps 10 + Coffee bar + Game Room + Train to CHGO

Brookfield (Near Chicago)

Sleeps 10 + Coffee bar + Game Room + Train to CHGO offers accommodations in Brookfield, 13 miles from Union Station and 13 miles from Willis Tower.

Scored out of 10, guest rating 10

Exceptional - What previous guests thought, 5 reviews

Price from

$554.79

1 night, 2 adults

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Woodlawn Oasis

Chicago

Woodlawn Oasis offers accommodations in Chicago, 1.6 miles from 63rd Street Beach and 1.8 miles from Museum of Science and Industry - Chicago.

H

Heather

From

United States

The house is beautiful and on a quiet street. We were able to cook and have family time quite comfortably.

Scored out of 10, guest rating 9.0

Wonderful - What previous guests thought, 13 reviews

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BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12

Chicago

BOUTIQUE GARDEN HOUSE CHICAGO 3-STORY sleeps 12 offers accommodations in Chicago, 4 miles from Museum of Science and Industry - Chicago and 5.1 miles from Guaranteed Rate Field.

M

Micheala

From

United States

Loved our stay at the Garden. The house was bery clean, and the beds were perfect! Our host was very responsive. Thank you

Scored out of 10, guest rating 9.7

Exceptional - What previous guests thought, 6 reviews

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Breathtaking Downtown Penthouse B - Sleeps 11

Near North Side, Chicago

Breathtaking Downtown Penthouse B - Sleeps 11 is located in Chicago, just a 17-minute walk from Chicago Museum of Contemporary Art and 1.1 miles from Shops at Northbridge.

S

Sajjad

From

United States

The property was very clean and neat, great views from the balcony and rooftop.

Scored out of 10, guest rating 9.2

Wonderful - What previous guests thought, 19 reviews

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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.

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