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Featured Condos in Chicago

$70
Spacious Studio in Chicago Uptown/margate Park

Spacious Studio in Chicago Uptown/margate Park

Chicago, IL
Located in Uptown, this condo building is 0.6 mi (0.9 km) from Aragon Entertainment Center and within 3 mi (5 km) of Loyola University Chicago and Wrigley Field. Lincoln Park and Briar Street Theatre are also within 3 mi (5 km). Argyle Station is 7 minutes by foot and Lawrence Station is 11 minutes.
 
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Cute & Cozy Oak Park Condo With Deck & Jacuzzi tub , Near Everything!

Cute & Cozy Oak Park Condo With Deck & Jacuzzi tub , Near Everything!

Oak Park, IL
This condo features an outdoor tennis court and a spa tub.
 
$67
Mid-century Oasis in Trendy Logan Square

Mid-century Oasis in Trendy Logan Square

Chicago, IL
Located in Avondale, this condo building is 1.6 mi (2.6 km) from Concord Music Hall and 2.3 mi (3.7 km) from Humboldt Park. Wrigley Field and Lincoln Park Zoo are also within 6 mi (10 km). Logan Square Station is 6 minutes by foot and Belmont Station (Blue Line) is 12 minutes.
 
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Newly Rehabbed Condo Near Loyola Med

Newly Rehabbed Condo Near Loyola Med

Forest Park, IL
Situated in Forest Park, this condo building is 2.7 mi (4.3 km) from Ernest Hemingway Museum and House and 2.7 mi (4.4 km) from Frank Lloyd Wright Home and Studio. Brookfield Zoo and Garfield Park are also within 6 mi (10 km). Forest Park Transit Center is 17 minutes by foot and Harlem- Forest Park Station is 19 minutes.
 
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Great for Business Travel! Equipped Suite With Pool Access + Free Breakfast

Great for Business Travel! Equipped Suite With Pool Access + Free Breakfast

Lincolnshire, IL
An indoor pool is available at this condo.
 
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Phenomenal 1 Bedroom Streeterville Condo

Phenomenal 1 Bedroom Streeterville Condo

Chicago, IL
An indoor pool is available at this condo.
 
$70
The Seneca Just Blocks From Lake Michigan

The Seneca Just Blocks From Lake Michigan

Chicago, IL
This condo features a fitness center and a rooftop terrace. A terrace is also provided.
 
$149
Old Town #2- 2bd/2ba- 2 Blcks to Lincoln Park Zoo-walk to Beach

Old Town #2- 2bd/2ba- 2 Blcks to Lincoln Park Zoo-walk to Beach

Chicago, IL
Located in Lincoln Park, this condo building is within a 10-minute walk of Second City and Chicago History Museum. Lincoln Park Zoo and Lincoln Hall are also within 1 mi (2 km). Sedgwick Station is only a 3-minute walk and North-Clybourn Station is 13 minutes.
 
$67
Comfy Condo Sleeps 8, Mins From O'hare & Rosemont

Comfy Condo Sleeps 8, Mins From O'hare & Rosemont

Chicago, IL
Situated in Chicago, this condo building is within 6 mi (10 km) of Rosemont Theatre, Donald E. Stephens Convention Center, and Rivers Casino. Fashion Outlets of Chicago and MB Financial Park at Rosemont are also within 6 mi (10 km). River Grove Station is 13 minutes by foot and Franklin Park Belmont Ave Station is 30 minutes.
 
$95
6 King Bed Old Town / Downtown Retreat - The Best Fit for Large Groups!

6 King Bed Old Town / Downtown Retreat - The Best Fit for Large Groups!

Chicago, IL
Located in Near North Side, this condo building is within a 15-minute walk of Second City and Chicago History Museum. Lincoln Park Zoo and John Hancock Center are also within 2 mi (3 km). Sedgwick Station is 6 minutes by foot and North-Clybourn Station is 12 minutes.
 
$99
Luxury Designer Loft Just 2,5 Miles From Magnificent Mile!

Luxury Designer Loft Just 2,5 Miles From Magnificent Mile!

Chicago, IL
Located in West Town, this historic condo building is within 3 mi (5 km) of United Center, UIC Pavilion, and Merchandise Mart. Douglas Park is 3 mi (4.8 km) away. Chicago Western Avenue Station (Milwaukee District-West) is 15 minutes by foot and Damen Station is 23 minutes.
 
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Brand New Luxury Condo

Brand New Luxury Condo

Chicago, IL
Located in Logan Square, this condo building is 0.6 mi (0.9 km) from Concord Music Hall and within 3 mi (5 km) of DePaul University-Lincoln Park and Lincoln Hall. Humboldt Park is 1.7 mi (2.7 km) away. California Station (Blue Line) is only a 2-minute walk and Logan Square Station is 14 minutes.
 
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Vacation Condos in Chicago

Wandering around in search of the best restaurants, snapping pictures of iconic landmarks, and hiking through local landscapes are just a few of the things you love about taking a vacation. But you sometimes miss the comforts of home during your getaways. Next time, bring home with you! Book a condominium through Travelocity, and you can have all your travel needs met. You’ll still be able to experience Chicago, but you won’t have to give up the things you love—like a full kitchen to cook your favorite breakfast, a nice quiet spot to catch up on reading, and easy access to the top sites in the city.

There are tons of vacation condo rentals to suit your travel style. Do you want to stay in downtown condos that will put you in the heart of Chicago? Or do you prefer a luxury condo in an upscale neighborhood, conveniently located near the best attractions?

Place yourself in any part of the city and spend your days exploring the new world around you. When you tire of seeing the sights and testing coffee in the local cafes, return to your safe haven—your condo rental. You’ll appreciate that you can sleep in late without worrying about hotel staff knocking on your door, and you can head out onto the city street without being pegged as a tourist.

You don’t have to pay prices that resemble a mortgage when you book a condo through Travelocity. Our variety of vacation rentals will let you—and your wallet—feel like you’ve made the right decision. Browse properties today and start deciding what outfits you’ll pack for the trip.

Top Trending Hotels in Chicago

See all 2,513 Properties in Chicago
Warwick Allerton - Chicago $79
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.