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The 10 Best Cottages in Chicago, USA

Check out our pick of great cottages 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.

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.

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9.3
Superb
121 reviews
Price from
₪ 1,414
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.

Fantastic property very close to the downtown area of Chicago, near the metro and the bus stop. Beautifully done up interiors, Very spacious and can easily accommodate 12-14 people . Ample amount of coffee milk and sugar at disposal. Prompt replies from the owner for everything we needed.

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9.6
Exceptional
7 reviews
Price from
₪ 1,601
per night

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 located in Chicago. The air-conditioned accommodation is 3.8 km from Museum of Science and Industry - Chicago, and guests can benefit from on-site private parking and complimentary WiFi. Adler Planetarium & Astronomy Museum is 11 km away and Willis Tower is 12 km from the holiday home.

The property had a lot of space and the host was a good host.

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9.1
Superb
16 reviews
Price from
₪ 2,403
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.

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9.4
Superb
7 reviews
Price from
₪ 1,766
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.

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9.8
Exceptional
22 reviews
Price from
₪ 1,414
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.

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9.7
Exceptional
7 reviews
Price from
₪ 1,909
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.

I like the fact that it was close to bus stop and train stop. Overall nice building with roof top views. Garage parking.

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8.3
Very good
6 reviews
Price from
₪ 1,683
per night

Situated in Chicago, 2.8 km from Water Tower Chicago and 2.9 km from United Center, Central Chicago Suite2 Access to Patio features air-conditioned accommodation with a patio and free WiFi. The property is around 3.3 km from 360 Chicago, 3.7 km from Shops at Northbridge and 3.8 km from Union Station. The property is non-smoking and is located 3.1 km from Chicago Museum of Contemporary Art.

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8
Very good
6 reviews
Price from
₪ 1,067
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!

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8.7
Fabulous
7 reviews
Price from
₪ 1,042
per night

The holiday home is equipped with 3 bedrooms, 3 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a terrace with garden views. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. A dressing room and laundry service is also available.

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.

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8.5
Very good
24 reviews
Price from
₪ 1,734
per night

Most booked hotels in Chicago in the past month

Chicago's best hotels with breakfast

  • The Avondale Guesthouse
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 121 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

  • Stunning Condo #2 - Downtown River North
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 7 reviews

    Boasting air-conditioned accommodation with a patio, Stunning Condo #2 - Downtown River North is situated in Chicago.

    The location, the amount of bathrooms and bedrooms

  • 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...

  • 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.

  • Spacious 5-BR House near Transit w Parking
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 7 reviews

    Located in Chicago in the Illinois region, Spacious 5-BR House near Transit w Parking features a balcony. This property offers access to a terrace, free private parking and free WiFi.

    I came for my son’s birthday and he loved it very spacious and great communication

  • Breathtaking Downtown Penthouse A - Sleeps 11
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 6 reviews

    Boasting air-conditioned accommodation with a patio, Breathtaking Downtown Penthouse A - Sleeps 11 is set in Chicago.

  • Central Chicago Suite2 Access to Patio
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 6 reviews

    Situated in Chicago, 2.8 km from Water Tower Chicago and 2.9 km from United Center, Central Chicago Suite2 Access to Patio features air-conditioned accommodation with a patio and free WiFi.

  • Chic Green l Near Downtown & IL Medical District
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 7 reviews

    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.

  • The Black And White Suite
    7.0
    Scored 7.0
    Good
    Rated good
     · 1 review

    The Black And White Suite is situated in the Bronzeville district of Chicago, 3.2 km from Guaranteed Rate Field, 5.4 km from Museum of Science and Industry - Chicago and 6.3 km from Field Museum of...

  • Tranquil Urban Retreat
    Free cancellation options available
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 2 reviews

    A recently renovated holiday home in Chicago, Tranquil Urban Retreat offers outdoor fireplace, parking on-site and sports facilities.

  • Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 24 reviews

    Featuring a garden and inner courtyard views, this 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.

  • very nice house in chicago
    Free cancellation options available
    1.0
    Scored 1.0
    Very poor
    Rated very poor
     · 1 review

    Offering city views, very nice house in chicago is an accommodation situated in Chicago, 12 km from Shops at Northbridge and 12 km from 360 Chicago.

  • Chicago Vacation Rental, 19 Mi to Downtown Area!

    Situated in Chicago, 19 km from Museum of Science and Industry - Chicago and 23 km from Guaranteed Rate Field, Chicago Vacation Rental, 19 Mi to Downtown Area! offers air conditioning.

  • Chicago Big House
    Free cancellation options available

    Set in Chicago in the Illinois region, Chicago Big House has a terrace and garden views. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Luxe SFH in the Heart of Old Town

    Set in Chicago, 1.2 km from North Avenue Beach and 2 km from Fullerton Beach, Luxe SFH in the Heart of Old Town offers air conditioning.

FAQs about hotels in Chicago





Cottages that guests love in Chicago

  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 463 reviews
    Location excellent. View and balcony fabulous. Bed 6 ft cosy. Lots of stuff in bathroom, kitchen and washroom. Very secure. Excellent communication from Kasa.
    SHEILA
    Ireland
  • 8.5
    Scored 8.5
    Very good
    Rated very good
     · 10 reviews
    The aparment is beautiful. Location is great. Please keep in mind, metro is a 30 minute walk, but if you have a CTA Pass, you can get there by bus, which stops pretty much at the door! Neighbourhood looks good, and felt very safe. The apartment is perfectly equipped and very cozy. We felt like at home!
    Daniel
    Spain
  • From ₪ 801.90 per night
    6.0
    Scored 6.0
    Pleasant
    Rated pleasant
     · 9 reviews
    Incredible location. Rogers Park is a great neighborhood. Trains to the city are nearby. Tucked away apartment that is charming and comfortable.
    C
    CONNOR
    United States
  • From ₪ 824.43 per night
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 5,037 reviews
    The view was great, the room cosy and comfy. Great place to explore Chicago from. Price was hard to beat.
    Pavel
    Slovakia
  • From ₪ 824.43 per night
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 3,986 reviews
    Location is the best in Chicago. If you are going to the city for visiting, this is the best location. Just in the heart of Chicago loop, in front of the Chicago River, easy walking to the millennium park, magnificent mile, skydeck, river walk, cloud gate, Chicago art institute, grant park and others. It is a historic building, with a beautiful lobby. My room was small, but was clean and cozy and a coffee machine was available. Coffee, milk, sugar supplied free by the hotel . Nice team providing support and service.
    Maria Sidalina
    Brazil
  • From ₪ 692.52 per night
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 276 reviews
    Charming B&B in Oldtown Chicago. High standard, delicious breakfast and smooth WhatsApp communication with the team.
    Dirk
    Germany
  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 463 reviews
    Well equipped and comfortable apartment with a great view. Good facilities for self catering. Great to have a balcony to sit out on. Efficient system for the elevators (we were on the 27th floor). Comfortable beds, including the sofa bed. Excellent area with subway and excellent Wholefoods grocery store nearby.
    Julie
    New Zealand
  • 8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 65 reviews
    A great getaway within easy reach of all the downtown sights, via the "L' subway system. Considering we let ourselves into the wrong apartment, we were very comfortable and found our host Safa charming and helpful.
    Roger
    New Zealand
  • From ₪ 928.58 per night
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 560 reviews
    Comfortable bed Big cosy room with nice and thick carpet Huge TV Very clean Quiet hotel and neighborhood The hotel is just a stone's throw from lake Michigan and very close to shops and restaurants Helpful staff who provided me with a kettle when I asked for one. Fireplace in the lobby
    Victor
    France
  • From ₪ 689.92 per night
    7.9
    Scored 7.9
    Good
    Rated good
     · 541 reviews
    Charming , if a little torn, place close to restaurants in Broadway. The Room with the fireplace and Baseball memorabilia , an free cofee, is worth seing
    Jorgen
    Norway

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