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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+
Our top picks Lowest Price First Star rating and price Top reviewed

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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.

Central to where wanted to visit. Large property that was very comfortable.

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9.3
Wonderful
122 reviews
Price from
$264
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.

The housekeeper was very friendly. The location is great: a more calm area but with the Chicago Elevated in walking distance. The breakfast is outstanding compared to US hotel standards in this price range. Rooms are comfortable and clean.

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9.4
Wonderful
274 reviews
Price from
$175.20
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.

We LOVED this place! The house was adorable and cute. All the decor was so fun, Ashley was beyond friendly, the breakfast was incredible, snacks always downstairs. The neighborhood was great...we want to move in, please take us :))

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9.6
Exceptional
208 reviews
Price from
$165.99
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
$250
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
$131.40
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 whole place was so tastefully decorated. Everything you could need or want was there provided for you. The location was great and free parking out front made it very comfortable.

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9.8
Exceptional
10 reviews
Price from
$278.46
per night

Offering garden views, Chicago Charm is an accommodation set in Chicago, 11 km from Lincoln Park Zoo and 13 km from 360 Chicago. The air-conditioned accommodation is 2.6 km from Loyola University Chicago, and guests can benefit from private parking available on site and free WiFi. The property is non-smoking and is located 6.6 km from Wrigley Field.

Very clean, comfortable, and homey. Can highly recommend .Smooth transaction and seamless visit.

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9.7
Exceptional
34 reviews
Price from
$171.85
per night

Most booked vacation rentals in Chicago this month

Enjoy breakfast in Chicago!

  • The Polo Inn Bridgeport U.S.A.
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 65 reviews

    Just 6 miles south of the Chicago city center, this Bridgeport B&B is 3 minutes’ drive from U.S. Cellular Field, home of baseball’s White Sox.

    It was cozy,charming and in such a perfect location.

  • 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
     · 274 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
     · 208 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

  • Fully Furnished Apt Near Millenium Park- 29
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 11 reviews

    Fully Furnished Apt Near Millenium Park- 29 features accommodations within half a mile of the center of Chicago, with free Wifi and a kitchen with a dishwasher, an oven, and a microwave.

    Great location. Easy to book. Clean and 24 hour security

These vacation rentals in Chicago have options with FREE cancellation

  • Sentral Michigan Avenue
    Free cancellation options available
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 1,106 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.

  • The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
    8.3
    Scored 8.3
    Very Good
    Rated very good
     · 255 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!

  • Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 40 reviews

    Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking is a recently renovated apartment in Chicago where guests can make the most of the garden and tennis court.

    Very comfortable and very clean place, I recommend it 100%

  • Wrigleyville Friends Unit - 5bdrm
    Free cancellation options available
    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.

  • ONE ROOM in AN APT HAVEN
    Free cancellation options available
    5.5
    Scored 5.5
    Average
    Rated fair
     · 2 reviews

    ONE ROOM in AN APT HAVEN is located in Chicago, just 6.9 miles from Lincoln Park Zoo and 7.2 miles from Wrigley Field. The air-conditioned accommodation is 6.1 miles from United Center.

  • Langley
    Free cancellation options available
    5.2
    Scored 5.2
    Average
    Rated fair
     · 41 reviews

    Langley in Chicago provides adults-only accommodations with a tennis court and a shared lounge. This guest house provides free private parking, a shared kitchen, and free Wifi.

    The rooms were really nice and the bed comfortables.

  • Cozy 2 brm apartment mins away from United Center
    9.3
    Scored 9.3
    Wonderful
    Rated wonderful
     · 11 reviews

    Cozy 2 brm apartment mins away from United Center is located in Chicago, just 1.2 miles from United Center and 3.2 miles from Union Station.

    It was so beautiful and comfortable I didn’t want to leave 🥰

  • The Twin Lions: Bespoke Travel Lodge w/ Speakeasy*
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 10 reviews

    The Twin Lions: Bespoke Travel Lodge w/ Speakeasy* is a recently renovated apartment in Chicago where guests can make the most of the garden and bar.

    Well located, VERY CLEAN, unique decor, stocked kitchen.

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.

  • Chicago Charm
    8.0+ review score
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 34 reviews

    Chicago Charm offers accommodations in Chicago, 1.6 miles from Loyola University Chicago and 4.1 miles from Wrigley Field.

    I liked that we had private parking and plenty of room.

  • Romantic 3 Bed Home In The Heart Of The Park
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 16 reviews

    Romantic 3 Bed Home In The Heart Of The Park is located in Chicago, just 2.3 miles from Museum of Science and Industry - Chicago and 3.8 miles from Guaranteed Rate Field.

  • City Villa Sleeps 10-20 Free TV & Parking
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 9 reviews

    City Villa Sleeps 10-20 Free TV & Parking is a recently renovated apartment in Chicago, near Wrigley Field.

    Beliggenhet var helt fint. Greit å reise dit vi skulle både med buss og bane.

  • Winter Wonderland Retreat and Your Chicago Chill Getaway
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 11 reviews

    Featuring a tennis court, Winter Wonderland Retreat and Your Chicago Chill Getaway features accommodations in Chicago.

    広い。綺麗。洗濯機と洗剤が準備されている。都心部には行きやすく周りは静か。オーナーとは結局一度も話さなかったが十分にコミュニケーションがとれた。タオルはある。

  • Spacious Row Home next Transit near Downtown w Parking
    9.4
    Scored 9.4
    Wonderful
    Rated wonderful
     · 7 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
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 22 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.

  • Vibrant and Modern 2-Bedroom Home Near Downtown
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 7 reviews

    Vibrant and Modern 2-Bedroom Home Near Downtown offers accommodations in Chicago, 1.1 miles from United Center and 3.1 miles from Union Station.

FAQ about vacation rentals in Chicago









Vacation Rentals That Guests Love in Chicago

  • Avg. price/night: $276.41
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 906 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: $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: $270.98
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 90 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: $276.41
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 906 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
     · 363 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
  • 8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 20 reviews
    Great location for us. Our daughter and family also live in Roscoe Village
    Sue
    Young couple
  • Avg. price/night: $224.42
    6.9
    Scored 6.9
    Pleasant
    Rated pleasant
     · 228 reviews
    Loved the way the villa was decorated and gave a homely vibe.
    T
    Tikisha
    Solo traveler

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