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The 10 Best Holiday Rentals in Chicago, USA

Check out our pick of great holiday rentals in Chicago

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Review score

Superb: 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.

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

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9.3
Superb
120 reviews
Price from
£421
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
Superb
267 reviews
Price from
£145
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
205 reviews
Price from
£146
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
£87
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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9.6
Exceptional
7 reviews
Price from
£168
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
£3,017
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
9 reviews
Price from
£385
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
Superb
11 reviews
Price from
£189
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
£429
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.

Every detail has been considered to make you feel at home. It has everything a house should have. The decoration is very nice and relaxing. The beds are comfortable. Sheets and towels are clean. Ventilation works well. It was fun to watch movies on the big screen TV. Wi-fi provides very fast internet. The location of the house is very close to the city. You can reach the city center in approximately 20 minutes by car. You can park your car in the private parking lot at the back. There is a seating area on the back balcony. Very useful in nice weather. If I go to Chicago again, I will definitely stay here.

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9.8
Exceptional
32 reviews
Price from
£321
per night

Most booked holiday rentals in Chicago this month

Enjoy breakfast in Chicago!

  • The Polo Inn Bridgeport U.S.A.
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 65 reviews

    Just 6 miles south of the Chicago city centre, 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
    Superb
    Rated superb
     · 120 reviews

    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.

    i like the games,couches and smart tv with good inter

  • The Sono Chicago
    Breakfast options
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 268 reviews

    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 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
     · 205 reviews

    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.

    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

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

  • The Penthouse, Lux stay near Downtown, UofC & Lake
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 7 reviews

    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...

  • 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 accommodation within less than 1 km of the centre 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
     · 9 reviews

    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.

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

These holiday rentals in Chicago have options with FREE cancellation

  • Sentral Michigan Avenue
    Free cancellation options available
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 1,073 reviews

    Sentral Michigan Avenue offers accommodation within 1.8 km of the centre 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 2BR Flats -Cubs!- Located Right next to Wrigley and Transit
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 251 reviews

    In the Lakeview district of Chicago, close to Wrigley Field, The Double Play, Wrigley 2BR Flats -Cubs!- Located Right next to Wrigley and Transit has free WiFi and a washing machine.

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

  • 5430 Happy Home
    Free cancellation options available
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 257 reviews

    Featuring a garden, 5430 Happy Home is set in Chicago, within 4.4 km of Museum of Science and Industry - Chicago and 5 km of Guaranteed Rate Field. All common areas and bathrooms are shared.

    Facilities, location, staff's response, wonderful word

  • 15 min Ohare/Rivers Casino/Downtown & Parking2
    6.8
    Scored 6.8
    Pleasant
    Rated pleasant
     · 12 reviews

    Situated in Chicago, 11 km from Wrigley Field and 14 km from Lincoln Park Zoo, 15 min Ohare/Rivers Casino/Downtown & Parking2 offers a garden and air conditioning.

  • Red Line GUEST HOUSE apartment corporate housing
    7.2
    Scored 7.2
    Good
    Rated good
     · 10 reviews

    A recently renovated apartment situated in Chicago, Red Line GUEST HOUSE apartment corporate housing features a garden. This property offers access to a balcony, free private parking and free WiFi.

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

    Langley in Chicago provides adults-only accommodation with a tennis court, a terrace 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
    Superb
    Rated superb
     · 11 reviews

    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.

    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 its garden and bar.

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

Highly rated holiday rentals in Chicago

  • Chicago Charm
    8.0+ review score
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 32 reviews

    Offering garden views, Chicago Charm is an accommodation set in Chicago, 11 km from Lincoln Park Zoo and 13 km from 360 Chicago.

    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
    Superb
    Rated superb
     · 16 reviews

    Situated 6.2 km from Guaranteed Rate Field, 11 km from Art Institute of Chicago and 11 km from Field Museum of Natural History, Romantic 3 Bed Home In The Heart Of The Park features accommodation...

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

    Set in Chicago, City Villa Sleeps 10-20 Free TV & Parking is a recently renovated accommodation, 2.5 km from North Avenue Beach and 1.9 km from 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

    Boasting accommodation with a patio, Winter Wonderland Retreat and Your Chicago Chill Getaway is set 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
    Superb
    Rated superb
     · 7 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
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 22 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.

  • Vibrant and Modern 2-Bedroom Home Near Downtown
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 6 reviews

    Situated in Chicago, 1.7 km from United Center and 5.1 km from Union Station, Vibrant and Modern 2-Bedroom Home Near Downtown features spacious air-conditioned accommodation with a terrace and free...

  • McCormick Place Skyline view 2br-2ba with Optional parking for 6 guests
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 6 reviews

    Located in Chicago, 2.4 km from Field Museum of Natural History and 2.9 km from Art Institute of Chicago, McCormick Place Skyline view 2br-2ba with Optional parking for 6 guests offers a fitness...

FAQ about holiday rentals in Chicago








Holiday rentals that guests love in Chicago

  • Avg. price/night: £255.54
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 63 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 traveller
  • Avg. price/night: £212.36
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 86 reviews
    Looks like a vacation house
    L
    Linh
    Young couple
  • 9.3
    Scored 9.3
    Superb
    Rated superb
     · 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
    People with friends
  • Avg. price/night: £255.54
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 63 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: £233.60
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 904 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
  • Avg. price/night: £300.74
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 361 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
     · 894 reviews
    Location, close to the Loop and in the middle of the Hellenic village
    Josue
    Solo traveller
  • 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: £312.08
    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 traveller

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