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Featured Cottages in Chicago

$210
Amazing Summer Lake Escape in our Waterfront Cottage!!!

Amazing Summer Lake Escape in our Waterfront Cottage!!!

Ingleside, IL
A garden is available at this cottage.
 
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Cute Waterfront Cottage On Long Lake W/ 50 Foot Private Dock & Pier

Cute Waterfront Cottage On Long Lake W/ 50 Foot Private Dock & Pier

Ingleside, IL
A garden is available at this cottage.
 
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A Diamond in the Rough

A Diamond in the Rough

Fox Lake, IL
Situated in Fox Lake, this historic cottage is within 9 mi (15 km) of Volo Bog State Natural Area, Volo Auto Museum, and Lake Miltmore Beach. Wilmot Mountain and Jones Island Beach are also within 12 mi (20 km). Fox Lake Station is 20 minutes by foot.
 
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Chicago Cottages For Rent

Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Chicago that will make you feel like you’ve stepped inside your vacation dreams.

The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.

These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Chicago is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?

Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…

Top Trending Hotels in Chicago

See all 2,539 Properties in Chicago
Warwick Allerton - Chicago $94
Warwick Allerton - Chicago

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL
     
    4.0 out of 5.0 Stars

    This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Water Tower Place and Chicago Water Tower are also within 5 minutes. Chicago Station (Red Line) is 6 minutes by foot and Grand Station (Red Line) is 8 minutes.

    Congress Plaza Hotel $79
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
       
      3.5 out of 5.0 Stars

      Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building and Buckingham Fountain are also within 5 minutes. Harrison Station and Chicago Van Buren Street Station are within a 5-minute walk.

      Eurostars Magnificent Mile, previously Dana Hotel $89
      Eurostars Magnificent Mile, previously Dana Hotel

      Eurostars Magnificent Mile, previously Dana Hotel

      660 North State Street, Chicago, IL
         
        4.0 out of 5.0 Stars

        Located in River North, this spa hotel is steps from Chinese Consulate and State Street. Water Tower Place and Michigan Avenue are also within 10 minutes. Chicago Station (Red Line) and Grand Station (Red Line) are within a 5-minute walk.

        The Whitehall Hotel $60
        The Whitehall Hotel

        The Whitehall Hotel

        105 E Delaware Pl, Chicago, IL
           
          4.0 out of 5.0 Stars

          Located in Near North Side, this romantic hotel is steps from 900 North Michigan Shops, John Hancock Center, and Water Tower Place. Michigan Avenue and State Street are also within 5 minutes. Chicago Station (Red Line) is 6 minutes by foot and Clark-Division Station is 11 minutes.

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          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.