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The 10 Best Cottages in Chicago, USA

Check out our pick of great cottages in Chicago

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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
121 reviews
Price from
£420
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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9.8
Exceptional
5 reviews
Price from
£125
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
£522
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
£383
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
£307
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
£387
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
£124
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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8.2
Very good
5 reviews
Price from
£189
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
£377
per night

Set in Chicago, 2.4 km from Ohio Street Beach and 2.7 km from North Avenue Beach, Beautifully Remodeled Flat Downtown #3N offers air conditioning. The property is situated 1.8 km from Shops at Northbridge, 2.7 km from CIBC Theatre and 2.7 km from Millennium Station. Free WiFi is available throughout the property and Oak Street Beach is 1.7 km away.

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8
Very good
1 reviews
Price from
£104
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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  • Stunning Condo #2 - Downtown River North
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 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

  • 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.

  • 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.

  • 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.

These cottages in Chicago have options with FREE cancellation

  • Chic Green l Near Downtown & IL Medical District
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 5 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.

  • 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.

  • A terrific house for a large group.
    Free cancellation options available
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 4 reviews

    Set in Chicago, 11 km from Wrigley Field and 14 km from Lincoln Park Zoo, A terrific house for a large group. Offers air-conditioned accommodation with a terrace and free WiFi.

  • 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.

  • Brownstone in Gold Coast - Downtown
    Free cancellation options available

    Situated in the centre of Chicago, 600 metres from Oak Street Beach and 1.6 km from North Avenue Beach, Brownstone in Gold Coast - Downtown offers free WiFi and air conditioning.

  • 2 Newly Built Luxury Condos with Private Roofdeck

    Featuring air-conditioned accommodation with a patio, 2 Newly Built Luxury Condos with Private Roofdeck is located in Chicago.

  • Beautifully Remodeled Flat Downtown #3N
    Free cancellation options available
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 1 review

    Set in Chicago, 2.4 km from Ohio Street Beach and 2.7 km from North Avenue Beach, Beautifully Remodeled Flat Downtown #3N offers air conditioning.

  • Downtown Penthouse with Private Rooftop #2S
    Free cancellation options available
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located within the Near North Side district in Chicago, Downtown Penthouse with Private Rooftop #2S has air conditioning, a patio, and city views.

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

FAQ about cottages in Chicago





Cottages that guests love in Chicago

  • Avg. price/night: £204.95
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 2,564 reviews
    Great location! At the heart of the Loop. The room was cozy and nice.
    Ezgi
    Young couple
  • Avg. price/night: £390.97
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 937 reviews
    We had booked with Booking,com for 2 double beds, but got one king size bed instead. Our charming host (who's name escapes me) was very apologetic and dead set on making things right. He called us the very next day to arrange a transfer to a newly available room with 2 beds, and offered us complimentary drinks at your bar. We were settled and quite comfortable on the one big bed (I was travelling with my 21 yr. old son) so we actually chose to stay put. Your staff aims to please, and they do it well. They can take pride in their work...
    Pierre
    Family with young children
  • Avg. price/night: £203.51
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 1,082 reviews
    Amazing views and great location. We loved going in the hot tub in the morning
    Catherine
    Young couple
  • Avg. price/night: £267.16
    7.6
    Scored 7.6
    Good
    Rated good
     · 1,715 reviews
    ROOM, was adequate, cosy, but no kettle for us Tea loving Brits. The advice was to microwave to water, lol. LOCATION, was brilliant, just a short walk to the main attractions, heading in all directions. BREAKFAST, was ok, not the best for choice, I've had better, but plenty of. However, the Yanks dont do Brown Sauce or Baked Beans.
    Gary
    Young couple
  • Avg. price/night: £255.36
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 1,379 reviews
    Love the comfortable bed. The spacious room, cabinet space, and counter space in the bathroom. Shower and amenities were excellent. Loved the espresso machine
    Sharon
    Family with young children
  • 8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 30 reviews
    Really nice & cozy appartement, top Location and a fantastic city
    Lars
    Solo traveller
  • Avg. price/night: £305.24
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,198 reviews
    A brilliant spot, bang in the centre of Chicago with plenty of amenities. The room was very cozy, had an amazing view of the River (which hit the spot when tainted green for St Patrick's Day) and had everything one would need. We thoroughly enjoyed our stay!
    Andreu
    Family with young children
  • Avg. price/night: £224.22
    8.4
    Scored 8.4
    Very good
    Rated very good
     · 4,965 reviews
    Professional, friendly staff. Excellent location next to the river and a block from Michigan Avenue. Hotel was classic, upscale style. Our room was on the top floor with an incredible view. The small quarters were perfectly cozy as was the bed. The Nespresso machine was the ideal option for a shot of coffee.
    Lisa Grennier
    Young couple
  • Avg. price/night: £200.67
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 556 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
    Solo traveller
  • Avg. price/night: £185.59
    7.9
    Scored 7.9
    Good
    Rated good
     · 545 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
    Solo traveller

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