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The 10 Best Vacation Rentals in Chicago, USA

Check out our selection of great vacation rentals in Chicago

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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Sonder The Opal features accommodation within 700 metres of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave. The air-conditioned accommodation is 1.6 km from Oak Street Beach. North Avenue Beach is 2.8 km from the aparthotel and Shops at Northbridge is 700 metres away.

it’s a huge place, very well located, nice neighborhood. it’s near to greatest market places. it’s clean, with all equipment you need to stay comfortable. Linens are good quality. kitchens equipment are in great condition.

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9
Wonderful
120 reviews
Price from
$230.91
per night

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.

Everything was clean , working, and each detail to make your stay more cozy was provided

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9.3
Wonderful
121 reviews
Price from
$360
per night

The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 1.2 km away. Parking is free with permit provided by The Sono Chicago.

The rooms are fitted with a flat-screen TV with premium cable channels. Each room has an en suite bathroom with a large shower.

Everything is high quality. Bedding is great. Place is very quiet. Breakfast is great and perfect to start a day.

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9.4
Wonderful
272 reviews
Price from
$187.20
per night

Located near numerous restaurants and shops in the Bucktown neighbourhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service. Live entertainment at the Congress Theatre is 800 metres away.

Everything. The atmosphere, the staff, everything was incredible. I only wished I had stayed longer. Ashlee was very helpful and accommodating. I was upgraded to the room with a view and would highly recommend staying there.

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9.6
Exceptional
207 reviews
Price from
$175.99
per night

Set in Chicago, 1.4 km from 57th Street Beach, Studio with private bath room offers recently renovated accommodation with free WiFi and a garden. The air-conditioned accommodation is 2.4 km from 63rd Street Beach. The property is non-smoking and is located 1.2 km from Museum of Science and Industry - Chicago.

Very comfortable, quaint and cozy and clean. I felt safe in the neighborhood. The worst part is that I only stayed 2 days. I hope this property is available for my next visit.

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10
Exceptional
8 reviews
Price from
$91
per night

Situated in Chicago, 1.5 km from Oakwood Beach and 4.3 km from Museum of Science and Industry - Chicago, The Penthouse, Lux stay near Downtown, UofC & Lake features air-conditioned accommodation with a balcony and free WiFi. Guests can benefit from a patio and a sun terrace. The property is non-smoking and is located 4.8 km from Guaranteed Rate Field.

Great location, just what I was looking for.

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9.7
Exceptional
9 reviews
Price from
$199
per night

Fully Furnished Apts at The Mag mile -Cloud9 - 747 offers accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a microwave, a fridge and kitchenware. Less than 1 km from Oak Street Beach and a 17-minute walk from Ohio Street Beach, the property provides a rooftop pool and a garden. Private parking can be arranged at an extra charge.

Exactly as pictured. Beautiful, comfortable and clean

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9.9
Exceptional
7 reviews
Price from
$3,531
per night

Fully Furnished Apt Near Millenium Park- 29 features accommodation within less than 1 km of the centre of Chicago, with free WiFi, and a kitchen with a dishwasher, an oven and a microwave. 2.7 km from Ohio Street Beach and 400 metres from CIBC Theatre, the property offers a seasonal outdoor swimming pool and a garden. Private parking can be arranged at an extra charge.

This property is at a great location. It is nice and roomy. The kitchen is all furnished. Both the unit and the public areas are clean and easy to access.

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9.8
Exceptional
11 reviews
Price from
$379
per night

Located in Chicago, 1.9 km from United Center and 5.1 km from Union Station, Cozy 2 brm apartment mins away from United Center offers air conditioning. Both free WiFi and parking on-site are available at the apartment free of charge. The property is non-smoking and is set 6.2 km from Millennium Station.

Everything was clean and cozy, you’ll find everything you need - washing machine and dryer, hair dryer too, host was also really nice and prompt with respond

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9.3
Wonderful
11 reviews
Price from
$111.60
per night

The Twin Lions: Bespoke Travel Lodge w/ Speakeasy* is a recently renovated apartment in Chicago, where guests can make the most of its garden and bar. Among the facilities at this property are a concierge service and room service, along with free WiFi throughout the property. The property is non-smoking and is set 3.4 km from Lincoln Park Zoo.

The house was so beautifully decorated, enough space for all guests! It felt like we were in a movie.

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9.8
Exceptional
10 reviews
Price from
$278.46
per night

Most booked vacation rentals in Chicago this month

Enjoy breakfast in Chicago!

  • Villa D' Citta
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 62 reviews

    In the heart of Lincoln Park’s shopping and dining district, this modernized Chicago B&B features a private grotto and garden with BBQ facilities. Each romantic guest room comes with free Wi-Fi.

    The feel of the home is solid, stately, yet welcoming.

  • House 5863- Chicago's Premier Bed and Breakfast
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 19 reviews

    Modern and urban style décor is featured at this bed and breakfast in Chicago’s Andersonville neighborhood. Offering free WiFi access, Chicago’s Premier Bed and Breakfast is 3.1 mi from Wrigley Field.

    Great spread, many options, lovely outdoor seating.

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

    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

  • The Sono Chicago
    Breakfast options
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 272 reviews

    The Sono Chicago is located in The Old Town neighborhood of Chicago. Lincoln Park Zoo is only 0.7 mi away. Parking is free with permit provided by The Sono Chicago.

    The flushing of toilet in next room was sometimes a bit of a bother

  • Ray's Bucktown Bed and Breakfast
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 207 reviews

    Located near numerous restaurants and shops in the Bucktown neighborhood of Chicago, Ray's Bucktown features a communal sauna, free WiFi, and in-room breakfast service.

    Super unique and interesting plenty to do on and off property.

  • Studio with private bath room
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 8 reviews

    Just a 16-minute walk from 57th Street Beach and 0.8 miles from Museum of Science and Industry - Chicago, Studio with private bath room features accommodations in Chicago with a garden.

    The privacy, the silence. The neighborhood was very calm. It was close to the places I visited.

  • The Penthouse, Lux stay near Downtown, UofC & Lake
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 9 reviews

    The Penthouse, Lux stay near Downtown, UofC & Lake offers accommodations in Chicago, a 17-minute walk from Oakwood Beach and 2.7 miles from Museum of Science and Industry - Chicago.

  • Fully Furnished Apts at The Mag mile -Cloud9 - 747
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 7 reviews

    Fully Furnished Apts at The Mag mile -Cloud9 - 747 offers accommodations within 0.6 miles of the center of Chicago, with free Wifi and a kitchen with a microwave, a fridge, and kitchenware.

    Exactly as pictured. Beautiful, comfortable and clean

These vacation rentals in Chicago have options with FREE cancellation

  • Sonder The Opal
    Free cancellation options available
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 120 reviews

    Sonder The Opal features accommodations within 0.4 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    The location was great and the apartment was clean

  • Sentral Michigan Avenue
    Free cancellation options available
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 1,095 reviews

    Sentral Michigan Avenue offers accommodations within 1.1 miles of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    Very nice room, great kitchen. And there was everything you needed.

  • Sonder Jewelers Row
    Free cancellation options available
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 328 reviews

    Sonder Jewelers Row features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, a microwave, and a toaster.

    Location was good, property was clean and as pictured

  • The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 253 reviews

    The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit offers accommodations in Chicago, a 2-minute walk from Wrigley Field and 2.3 miles from Lincoln Park Zoo.

    Around the corner from Wrigley. Clean. Safe. Awesome!

  • Sonder South Wabash
    Free cancellation options available
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 496 reviews

    Sonder South Wabash offers accommodations in Chicago, 1.2 miles from Chicago Symphony Orchestra and 1.4 miles from CIBC Theatre. This condo hotel features an elevator and free Wifi.

    Location, everything works well within the apartment

  • Sonder The Burnham
    Free cancellation options available
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 65 reviews

    Sonder The Burnham offers accommodations within one mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    Good location, clean and nice fully equipped kitchen.

  • Sonder Market Hall
    Free cancellation options available
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 89 reviews

    Sonder Market Hall enjoys a location in Chicago, a 13-minute walk from United Center and 1.7 miles from Union Station.

    Easy entrance, great location, clean and beautiful.

  • The Neighborhood Hotel Lincoln Park
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 9 reviews

    The Neighborhood Hotel Lincoln Park in Chicago offers accommodations with free Wifi a 18-minute walk from Fullerton Beach, 1.2 miles from North Avenue Beach, and a 17-minute walk from Lincoln Park Zoo...

Highly-rated vacation rentals in Chicago

  • Casa Cerca De La Playa
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 17 reviews

    Providing a garden, Casa Cerca De La Playa provides accommodations in Chicago. This beachfront property offers access to free Wifi and free private parking.

    Friendly. Told me what he expected and was a nice person.

  • Contemporary 1BR Apartment with Wi-Fi! - Lockwood 1 & 2
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 5 reviews

    Contemporary 1BR Apartment with Wi-Fi! - Lockwood 1 & 2 offers accommodations in Chicago, 6.5 miles from United Center and 6.7 miles from Lincoln Park Zoo.

  • Charming 1BR Apt in North Center Near Shops- Larchmont 3
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 19 reviews

    Charming 1BR Apt in North Center Near Shops- Larchmont 3 is located in Chicago, just 5.5 miles from United Center and 5.8 miles from 360 Chicago.

    Great value for money. Easy check in instructions and good proximity to public transport.

  • 3BR Apartment Cozy Modern Living - Division 201W
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 26 reviews

    3BR Apartment Cozy Modern Living - Division 201W offers accommodations in Chicago, 3.3 miles from Union Station and 3.3 miles from Chicago Museum of Contemporary Art.

    Great service, clean, beds are comfortable 👌 I recommend it 100%

  • Complete & Comfy Studio Apt near Boystown - Oakdale 317 rep
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 20 reviews

    Complete & Comfy Studio Apt near Boystown - Oakdale 317 rep offers accommodations in Chicago, 1.2 miles from Wrigley Field and 1.3 miles from Lincoln Park Zoo.

    Loved the area and walk ability and restaurant scene.

  • 2BR Live in Style Designer Apt in Festive Boystown - Halsted 2A
    8.2
    Scored 8.2
    Very Good
    Rated very good
     · 18 reviews

    2BR Live in Style Designer Apt in Festive Boystown - Halsted 2A in Chicago features accommodations with free Wifi, 1.7 miles from Fullerton Beach, a 10-minute walk from Wrigley Field, and 2 miles from...

  • 3 bedroom in Best Location Parking Fireplace Patio Home office Pets Welcome
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 23 reviews

    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.

  • Wrigleyville Friends Unit - 5bdrm
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 12 reviews

    Wrigleyville Friends Unit - 5bdrm offers accommodations in Chicago, 1.7 miles from Fullerton Beach and a 9-minute walk from Wrigley Field.

    No breakfast. Location was good for us it’s an easy balk to Wrigley field.

FAQ about vacation rentals in Chicago








Vacation Rentals That Guests Love in Chicago

  • Avg. price/night: $387.11
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 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
  • 10
    Scored 10
    Exceptional
    Rated exceptional
     · 1 review
    One of the nicest vacation rental apartments I have stayed in. Very well appointed, kitchen had everything you could need including a full size washer and dryer. Having the back balcony was great.
    Marguerite
    Solo traveler
  • Avg. price/night: $233.46
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 89 reviews
    Looks like a vacation house
    L
    Linh
    Young couple
  • 9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 43 reviews
    Updated, well maintained. Nearby is a cozy little Italian village with restaurants and outdoor seating that was great! Overall it was beautiful, cozy and comfortable.
    Dawn
    Travelers with friends
  • Avg. price/night: $387.11
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 62 reviews
    The Villa is lovely and the host was great. They have great options for breakfast which you prepare yourself. Location was really nice - lovely the neighborhood. Loved the wine on tap!
    Sydney
    Group
  • Avg. price/night: $276.50
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 902 reviews
    Breakfast was convenient. Location can't be beaten. Rooms are unexpectedly roomy. The staff was extremely friendly and helpful. We enjoyed the Grillroom Chophouse (reasonable prices) across the street and the Italian Village (whimsical interior) down the block -- both recommended.
    Wilson
    Young couple
  • 8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 365 reviews
    The location was convenient to restaurants, and most importantly, to our family members in Ukrainian Village. The staff was friendly and helpful. Our room was very comfortable, very functional, and had an excellent shower.
    Joanne
    Young couple
  • 7.2
    Scored 7.2
    Good
    Rated good
     · 892 reviews
    Location, close to the Loop and in the middle of the Hellenic village
    Josue
    Solo traveler
  • 9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 30 reviews
    Magnolia Studios exceeded my expectations. The location was superb, and was perfect for a few days in town. Parking was never a problem. The studio itself was clean, comfortable, and quiet. Kitchen was adequately stocked with everything you may need for cooking a simple meal, and making a fresh cup of coffee with the Kuerig. As long as you read all instructions it's very simple to find the entrance. As an owner of my own vacation rental I would highly recommend Magnolia Studios.
    Amy
    Family with young children
  • Avg. price/night: $380.49
    8.0
    Scored 8.0
    Very Good
    Rated very good
     · 26 reviews
    Location is great. Our daughter lives in Ukrainian Village very convenient. The property is large enough, new and clean. Beds are very comfy!
    Michael
    Solo traveler

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