Skip to main content

The 10 Best Villas in Chicago, USA

Check out our pick of great villas in Chicago

Filter by:


Review score

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

See the latest prices and deals by choosing your dates.

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.

Great stay in a lovely little house, clean, well-decorated and very well-equipped. Close to local commerces and to north-south and east-west bus routes, and also to the river for walking or jogging away from the traffic. And next-door to a good Argentinian steak restaurant.

Show more Show less
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

Show more Show less
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.

Show more Show less
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.

Show more Show less
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.

Show more Show less
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.

Show more Show less
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.

Show more Show less
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.

Show more Show less
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!

Show more Show less
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.

Show more Show less
8.5
Very good
23 reviews
Price from
£374
per night

Looking for a villa?

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.
Search villas in Chicago

Most booked villas in Chicago this month

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: £240.05
    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

Research, refine and make plans for your whole trip

gogless