The 10 best cottages in Chicago, US | Booking.com
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Cottages in Chicago

Find the cottages that appeal to you the most

The best cottages in Chicago

Check out our selection of great cottages in Chicago

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Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Chicago and surrounding area in the past month

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Enjoy breakfast in Chicago and nearby

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 7 reviews

    Historic luxury Townhouse in Downtown Chicago is located in Chicago, just a 15-minute walk from Shops at Northbridge and 1.4 miles from Millennium Station.

  • Spacious 3-Bed West Loop Townhouse, 1 Car Garage is located in Chicago, just a 17-minute walk from Willis Tower and 1.4 miles from CIBC Theatre.

  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 1 review

    Offering a private beach area, Spectacular Gilded Age 6 Bedroom Gold Coast Mansion with Deck offers accommodations in the center of Chicago.

    From $1,973.17 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Gold coast villa with free parking garage sleeps 10 features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 8.8
    Excellent - What previous guests thought, 5 reviews

    Just a 13-minute walk from Water Tower Chicago and 0.6 miles from 360 Chicago, Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests features accommodations in Chicago with a garden.

  • Scored out of 10, guest rating 9.3
    Wonderful - What previous guests thought, 29 reviews

    Offering a garden, Designer Themed 4 Bedroom in Best Location with Patio and Fireplace offers accommodations in Chicago.

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 5 reviews

    A 19-minute walk from Oak Street Beach in Chicago, 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome provides accommodations with access to spa facilities and fitness room.

  • Located in Chicago, this holiday home is 0.7 mi from Lincoln Park Zoo and Downtown Chicago. Offering free private parking, the holiday home is 0.9 mi from 360 Chicago.

    From $1,417.87 per night

These cottages in Chicago and nearby have options with free cancellation

Traveling by car? These cottages in Chicago and nearby offer free parking

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    The Village Inn by Dakota Gal Digs is located in Chicago, just 1.8 miles from North Avenue Beach and 1.7 miles from Lincoln Park Zoo.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Featuring a bar, Amazing Penthouse Skyline Views! offers accommodations in Chicago. This property offers access to a balcony, free private parking, and free Wifi.

    From $910.99 per night
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 3 reviews

    Perfect Location Across from Park & Train Station is located in Chicago, just 2.9 miles from United Center and 4.6 miles from Union Station.

  • Wrigley 4BR Home, Sleeps 10 in Chicago features accommodations with free Wifi, a 13-minute walk from Wrigley Field, 3.4 miles from Lincoln Park Zoo, and 4.2 miles from Loyola University Chicago.

FAQ about cottages in Chicago

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Cheap vacations in Chicago

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Car rental in Chicago

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Hotels near Union Station

Perfect for local transit links.

Things to do in Chicago

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Hotels near McCormick Place

Places to stay near one of the top places to see.

Flights to Chicago

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Hotels near Chicago O'Hare International Airport

Got a layover, late arrival, or early departure? Find hotels conveniently close to the airport.

Hotels near Midway International Airport

Perfect for a late arrival or early departure.

Cottages in Illinois

Extend your search and explore the surrounding area.