Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

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Top deals for house rentals in Chicago

Find best vacation rental deals in Chicago and save up to 78%

Condo Lake View East
e.g. 1/7 - 1/14 (Sat - Sat)
-77%
$592
$135 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Irving Park
e.g. 2/3 - 2/10 (Fri - Fri)
-78%
$550
$120 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
4.5
"Outstanding" (4 ratings)
Irving Park, Chicago, Illinois, United States
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Apartment Little Village
e.g. 12/2 - 12/9 (Fri - Fri)
-47%
$110
$59 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Little Village, Chicago, Illinois, United States
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Pet-friendly rentals in Chicago

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

Apartment Ukrainian Village
$99 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.7
"Outstanding" (17 ratings)
Ukrainian Village, Chicago, Illinois, United States
Pet-friendly
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Apartment Near North
$223 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.7
"Outstanding" (37 ratings)
Near North, Chicago, Illinois, United States
Pet-friendly
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House South Loop
$225 per night
House ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (19 ratings)
South Loop, Chicago, Illinois, United States
Pet-friendly
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Accommodation with Internet in Chicago

Choose your ideal rental with Internet and WiFi in Chicago

Apartment Boystown
$77 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.7
"Outstanding" (16 ratings)
Boystown, Chicago, Illinois, United States
Internet
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Apartment Boystown
$113 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.8
"Excellent" (10 ratings)
Boystown, Chicago, Illinois, United States
Internet
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House Albany Park
$294 per night
House ∙ 14 guests ∙ 3 bedrooms
4.9
"Excellent" (32 ratings)
Albany Park, Chicago, Illinois, United States
Internet
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Vacation rentals with pool in Chicago

Discover best cabin and house rentals with pool in Chicago

Condo Near North
$197 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (15 ratings)
Near North, Chicago, Illinois, United States
Pool
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Apartment Streeterville
$112 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Streeterville, Chicago, Illinois, United States
Pool
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Condo Near North
$198 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (22 ratings)
Near North, Chicago, Illinois, United States
Pool
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Best vacation rental offers in Chicago

Apartment Boystown
$116 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.0
"Very good" (18 ratings)
Boystown, Chicago, Illinois, United States
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Condo West Town
$394 per night
Condo ∙ 9 guests ∙ 2 bedrooms
5.0
"Excellent" (178 ratings)
West Town, Chicago, Illinois, United States
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Apartment West Woodlawn
$101 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
West Woodlawn, Chicago, Illinois, United States
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Apartment Ravenswood
$91 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Ravenswood, Chicago, Illinois, United States
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Apartment Rush & Division
$200 per night
Apartment ∙ 5 guests ∙ 1 bedroom
4.7
"Outstanding" (8 ratings)
Rush & Division, Chicago, Illinois, United States
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Apartment East Village
$88 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.2
"Very good" (15 ratings)
East Village, Chicago, Illinois, United States
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Condo Tri-Taylor
$146 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (62 ratings)
Tri-Taylor, Chicago, Illinois, United States
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Condo Lake View East
$196 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (54 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Lake View
$101 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.2
"Very good" (12 ratings)
Lake View, Chicago, Illinois, United States
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Condo Near North
$217 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (17 ratings)
Near North, Chicago, Illinois, United States
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Aparthotel Near North
$221 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (183 ratings)
Near North, Chicago, Illinois, United States
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Apartment Near North
$129 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
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Condo Rogers Park
$143 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (122 ratings)
Rogers Park, Chicago, Illinois, United States
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Apartment Lake View East
$99 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.4
"Very good" (5 ratings)
Lake View East, Chicago, Illinois, United States
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House Rogers Park
$99 per night
House ∙ 6 guests ∙ 3 bedrooms
Rogers Park, Chicago, Illinois, United States
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Condo Roscoe Village
$269 per night
Condo ∙ 8 guests ∙ 3 bedrooms
4.7
"Outstanding" (14 ratings)
Roscoe Village, Chicago, Illinois, United States
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Apartment Chicago Loop
$108 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
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Apartment Hyde Park
$102 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (7 ratings)
Hyde Park, Chicago, Illinois, United States
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Apartment Chicago Loop
$130 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (2 ratings)
Chicago Loop, Chicago, Illinois, United States
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Apartment Tri-Taylor
$77 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Tri-Taylor, Chicago, Illinois, United States
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House Pulaski Park
$137 per night
House ∙ 8 guests ∙ 2 bedrooms
4.0
"Very good" (18 ratings)
Pulaski Park, West Town, Chicago
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Apartment Lake View East
$140 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (15 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Logan Square
$120 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Logan Square, Chicago, Illinois, United States
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Condo Buena Park
$202 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
"Excellent" (163 ratings)
Buena Park, Chicago, Illinois, United States
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Apartment Irving Park East
$73 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (24 ratings)
Irving Park East, Chicago, Illinois, United States
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Apartment Logan Square
$162 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Logan Square, Chicago, Illinois, United States
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Apartment West Woodlawn
$158 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
4.9
"Excellent" (12 ratings)
West Woodlawn, Chicago, Illinois, United States
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House Palmer Square
$196 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (16 ratings)
Palmer Square, Chicago, Illinois, United States
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Apartment Near North
$206 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.7
"Outstanding" (26 ratings)
Near North, Chicago, Illinois, United States
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Condo Rogers Park
$143 per night
Condo ∙ 8 guests ∙ 3 bedrooms
4.9
"Excellent" (136 ratings)
Rogers Park, Chicago, Illinois, United States
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Apartment Rush & Division
$155 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (42 ratings)
Rush & Division, Chicago, Illinois, United States
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Apartment West Town
$135 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.6
"Outstanding" (21 ratings)
West Town, Chicago, Illinois, United States
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Apartment West Town
$149 per night
Apartment ∙ 4 guests ∙ 4 bedrooms
4.8
"Excellent" (21 ratings)
West Town, Chicago, Illinois, United States
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House Uptown
$321 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (51 ratings)
Uptown, Chicago, Illinois, United States
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Apartment Woodlawn
$150 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Woodlawn, Chicago, Illinois, United States
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House Avondale
$151 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (55 ratings)
Avondale, Chicago, Illinois, United States
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Apartment North Center
$147 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (97 ratings)
North Center, Chicago, Illinois, United States
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Apartment Park West
$97 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (12 ratings)
Park West, Chicago, Illinois, United States
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House Sheffield Neighbors
$425 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (15 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Price and Availability Index in Chicago

Vacation Rental Price Information in Chicago

We looked at the prices of vacation rentals in each month and summarized them in the graph above. If you plan to book your accommodation in june, remember it's the most expensive period, with average prices of $358. However, prices of vacation houses and apartments are most competitive in february (2/4 - 2/11).

Rental Availability Information in Chicago

This graph displays the availability of vacation rentals in Chicago over the next 12 months. If you want to visit Chicago in November, make sure to book soon, as 77% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is April.

Chicago Apartments, Vacation Rentals, and Bed and Breakfast

Great view of downtown Chicago from your penthouse rental on Wimdu Welcome to Chicago, the third-largest city in the United States and veritable headquarters of the American Midwest. Chicago, also referred to as Chicagoland, The White City, and the Windy City, tends to be known for its deep dish pizza, tradition of jazz music, food and hard industries, and 1920s gangsterism and ‘bootlegging’ . Chicago is also the birthplace of the modern skyscraper and has over 1,200 complete skyscrapers grazing against its Lake Michigan horizon. The Chicago World’s Fair of 1893 put Chicago on the international playing field and dazzled the world with its brilliant architecture and display of traditional American values . Famous Chicagoans include Al Capone, Bill Murray, and Barack Obama. In this day and age, Chicago is also well known for its summer concert series Lollapalooza and it’s world-class art museums and collections, many with better collections than even the best Parisian exhibitions. Accommodation in Chicago comes in the form of vacation rentals, apartments for rent, and high-quality bed and breakfast options.

Chicago was once notable for its rampant ‘boosterism’, which is a promotional tactic used by politicians to wildly promote their city to encourage settlement and thereby inflate the cost of local real estate. These boastful, pompous attitudes in the press earned the city the infamous nickname of ‘The Windy City’ from newspapers across the Midwest, especially Cincinnati, Cleveland, and Detroit.

Deciding on a Chicago apartment, rental, or bed and breakfast for your Windy City trip

In making plans to visit the Midwest’s 'City That Just Works', it’s important to consider where you want to stay and how you want to experience the city. If you’re just in town for business or a conference, then it’s more advisable to find an economical, well-connected apartment rental in Chicago instead of a full-fledged vacation rental or bed and breakfast option. When coming in larger groups, getting a big rental in some of the more lively regions such as Wicker Park or North Side is certainly a better idea. Or why not try out staying in an apartment in North Lincoln, a more laid back and authentic area with fantastic old and ‘greystone’ architecture. Even an extravagant rooftop apartment in Chicago with a fantastic view of its famous skyline would not be a terrible idea; again, all depending on your trip needs.

What To Do and See: Art Museums, The Skyline, Local Insider Tips

So many visitors to Chicago from across the globe never really venture away from the downtown attractions, such as Grant Park, Michigan Avenue, or the various art museums. For a more local, ‘indie’ experience, head out to either Wicker Park or Bucktown. Check out one of the many ‘hipster’ cafés and restaurants, catering to all walks of life, including offering many exclusively vegan and vegetarian options. Chicago is also famous for its record and comic book stores, so make sure to check out some of these while in town!

Whether you are a sports fan, art lover, foodie, music junkie, looking to shop, or all of the above, you will find all kinds of options for anything that tickles your fancy. The world renowned Art Institute of Chicago houses several famous works as well as an incredibly vast collection of art of all styles. Also worth a look is the Adler Planetarium, the Field Museum of Natural History, and the Shedd Aquarium. Admire art without even entering a museum at all by checking out the city’s wonderfully diverse architecture. Chicago was home to the world’s first skyscrapers and still has some of the tallest buildings. There are numerous Frank Lloyd Wright buildings in the city as well. Take a walking architecture tour and wander past buildings designed by Daniel Burnham, Louis Sullivan, and Mies van der Rohe. Chicago also has lots of beautiful public art installations as well, such as the famous Cloud Gate at Millenium Park, also known as ‘The Bean’. We also recommend paying a visit to the famous Wrigley Field, home of Chicago baseball legends the Chicago Cubs.

Chicagoan Cuisine: From Kielbasa to Deep Dish Pizza

Look, Chicago is one of the United States’ premier destinations for amazing cuisine. The state of Illinois is the fourth largest when it comes to Mexican immigrant communities, and their cuisine is some of the best in the nation. No trip to Chicago is complete with having those spicy, local, Latin American tacos or tamales! We recommend finding a taco food truck and enjoying some of the more down-to-earth Latino cuisine. Along with the Mexican and Latino communities, there are strong Polish and German traditions in Chicago as well. For traditional Polish ‘kielbasa’ sausage, drop on by Kurowski’s Butcher Shop, a Polish supermarket with the best Polish sausage in town. For the best Polish ‘sit-down’ restaurant, go to Staropolska along North Milwaukee Avenue in Logan Square. For German fare, try out the Chicago Brauhaus, located in the popular Lincoln Square neighborhood. Or why not just sample the famous Chicago Hot Dog? This one differentiates itself from the rest of the nation’s hot dog varieties in its garnish of an entire pickle and liberal use of celery salt.

For traditional Chicago deep dish pizza, the best locale hands-down is Burt’s Place in Morton Grove, which is a smaller suburb a bit north of Chicago proper. It’s a traditional pizza joint with arguably the city’s best slice of deep dish.

Getting Around ‘Chi Town

The best way to get around Chicago is by taking what’s locally known as ‘The L’. The L is Chicago’s subway system and is one of the best in the entire country. Going both above and below ground, the L will get you to any section of the city for a meager $2.25, including dedicated train fare in The Loop, a circular section of the train service providing faster fare between the central downtown areas. Most tourists to Chicago end up staying inside the Loop during their trip, as this vicinity provides enough access to museums, bars, restaurants, and other shopping opportunities.

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