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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.

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

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9.3
Superb
122 reviews
Price from
£328
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
274 reviews
Price from
£148
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
£149
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
£86
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
£238
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
£3,594
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
£461
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
£182
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
£425
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
£278
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
     · 66 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
     · 122 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
     · 274 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
     · 208 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
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 9 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
     · 11 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
     · 1,108 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 Flats - Cubs! - Located Right next to Wrigley and Transit
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 255 reviews

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

    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
    Fabulous
    Rated fabulous
     · 40 reviews

    Located in Chicago, 7 km from Wrigley Field and 10 km from Lincoln Park Zoo, Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking provides air-conditioned accommodation with a balcony and...

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

  • Wrigleyville Friends Unit - 5bdrm
    Free cancellation options available
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 12 reviews

    Boasting air-conditioned accommodation with a balcony, Wrigleyville Friends Unit - 5bdrm is situated in Chicago.

    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 passable
     · 2 reviews

    Situated in Chicago, 10 km from United Center and 11 km from Lincoln Park Zoo, ONE ROOM in AN APT HAVEN offers a garden and air conditioning.

  • 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

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

    Set in Chicago, 6.9 km from Museum of Science and Industry - Chicago and 14 km from Guaranteed Rate Field, Casa Cerca De La Playa offers a garden and air conditioning.

    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

    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
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 7 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...

FAQ about holiday rentals in Chicago








Holiday rentals that guests love in Chicago

  • Avg. price/night: £180.68
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 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: £276.53
    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
  • 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: £153.50
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 91 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: £276.53
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 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: £180.68
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 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
  • Avg. price/night: £219.42
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 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
  • Avg. price/night: £555.63
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 20 reviews
    Great location for us. Our daughter and family also live in Roscoe Village
    Sue
    Young couple
  • Avg. price/night: £179.63
    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 traveller

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