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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.

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

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9.3
Superb
122 reviews
Price from
£330
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.

The location, the amount of bathrooms and bedrooms

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9.5
Exceptional
6 reviews
Price from
£233
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
£520
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
£408
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.

Staying at Northside FAMILYNEST Lincoln Sq was an absolute delight! From the cleanness,modern amenities to the beautifully decorated rooms and the delicious light snacks that were available to eat. Lastly our host Mr Ivan was great he made us feel right at home. I truly enjoyed our stay!

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9.8
Exceptional
22 reviews
Price from
£306
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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9.8
Exceptional
6 reviews
Price from
£499
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
Very good
5 reviews
Price from
£254
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
£221
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
£222
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
23 reviews
Price from
£376
per night

Looking for a cottage?

Cottages are perfect for travellers who enjoy feeling cosy and independent in the countryside. Usually small, traditionally built houses, cottages spread across one or two floors, making them great for families, or holidays with a little more privacy.
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Enjoy breakfast in Chicago!

  • 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

  • Stunning Condo #2 - Downtown River North
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 6 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
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 6 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
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 5 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.

These cottages in Chicago have options with FREE cancellation

  • 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.

  • 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.

  • Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 23 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.

  • 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.

  • The Black And White Suite
    Free cancellation options available
    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...

  • 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.

  • The Orleans - Floor 2 Private roof deck Patio
    Free cancellation options available

    Featuring air-conditioned accommodation with a patio, The Orleans - Floor 2 Private roof deck Patio is set in Chicago.

Travelling by car? These cottages in Chicago offer free parking!

FAQ about cottages in Chicago





Cottages that guests love in Chicago

  • Avg. price/night: £205.79
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 485 reviews
    The location was fantastic as was the building and foyer. They've really leaned into the heritage of the building which was fantastic as was the extra floors, one with an art gallery. We loved how easy it was to get around from here. The bathroom was very large and the style of the room was fantastic.
    Kieran
    Young couple
  • Avg. price/night: £181.38
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 2,824 reviews
    Small but cozy
    AlessandroTaipei
    Solo traveller
  • Avg. price/night: £178.54
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 5,012 reviews
    Cannot fault The River Hotel. The room was comfortable, clean & the facilities available were amazing. Level 2 coffee for guests that came highly recommended from staff & tasted amazing to a gym with amazing selection of equipment. The hotel was very charming.
    Kisha
    Young couple
  • Avg. price/night: £292.24
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1,625 reviews
    Beautiful Art Deco architecture and very comfortable lounge, bar area with a gorgeous fireplace and bistro.
    Kathy
    Young couple
  • Avg. price/night: £465.15
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 1,226 reviews
    Great location! We stayed in one of the spa rooms which was lovely and spacious. The gym was superb, as were the pool, sauna & steam room.
    Jennifer
    Young couple
  • Avg. price/night: £181.38
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 2,824 reviews
    I liked my stay! It was cozy, in a great location, and had everything that I needed. At first, I thought the room was a bit small, but as a solo traveler, it ended up feeling very cozy.
    Arieana
    Solo traveller
  • Avg. price/night: £121.30
    7.5
    Scored 7.5
    Good
    Rated good
     · 6,545 reviews
    comfortable room, very clean. Had a safe in the room and bathroom was good. Plenty of storage space for things in wardrobe etc. Coffee machine in room. Fitness suite nice enough but limited to gym equipment (no sauna/pool etc.).
    Adam
    Solo traveller
  • 8.3
    Scored 8.3
    Very good
    Rated very good
     · 237 reviews
    Great location. Very secure. Cozy beds. Nice room temperatures. Easy to get in and out, and close to the Red Line train. Very cute bathrooms with ample shampoo and conditioner, and hairdryers. Never had an issue accessing the bathrooms when needed. Cute kitchen with plenty of dishware. Fridge was not dirty. Bedrooms are separate from and above the common areas.
    J
    Jamie
    Solo traveller
  • Avg. price/night: £465.15
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 1,226 reviews
    Wow - this has got to be the best hotel we've ever stayed in, the room was fabulous, so comfortable and included a kitchenette for those morning hot beverages. On site pool, steam room and sauna was a great treat, we caught the sun rise a couple of times from the pool which opens at 6am for us early risers. Staff a really friendly.
    Jeanette
    Young couple
  • 9.3
    Scored 9.3
    Superb
    Rated superb
     · 11 reviews
    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
    Karolína
    People with friends

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