Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

Chicago
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Top deals for house rentals in Chicago

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

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

Condo Streeterville
$393 per night
Condo ∙ 7 guests ∙ 2 bedrooms
4.9
"Excellent" (46 ratings)
Streeterville, Chicago, Illinois, United States
Pet-friendly
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Apartment South Loop
$286 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.6
"Outstanding" (17 ratings)
South Loop, Chicago, Illinois, United States
Pet-friendly
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Apartment South Loop
$241 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.8
"Excellent" (38 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

Condo The Gap
$152 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.2
"Very good" (20 ratings)
The Gap, Chicago, Illinois, United States
Internet
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Apartment Lake View East
$169 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8
"Excellent" (24 ratings)
Lake View East, Chicago, Illinois, United States
Internet
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House Avondale
$397 per night
House ∙ 14 guests ∙ 5 bedrooms
4.5
"Outstanding" (41 ratings)
Avondale, 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

Apartment Chicago Loop
$253 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Chicago Loop, Chicago, Illinois, United States
Pool
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Apartment Chicago Loop
$202 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Chicago Loop, Chicago, Illinois, United States
Pool
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Apartment West Loop
$191 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
West Loop, Chicago, Illinois, United States
Pool
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Best vacation rental offers in Chicago

Apartment Roscoe Village
$132 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (152 ratings)
Roscoe Village, Chicago, Illinois, United States
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Condo West Town
$323 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (13 ratings)
West Town, Chicago, Illinois, United States
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Condo Near North
$238 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (16 ratings)
Near North, Chicago, Illinois, United States
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House Hollywood Park
$279 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (10 ratings)
Hollywood Park, Chicago, Illinois, United States
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Apartment University Village / Little Italy
$278 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (223 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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House Sheffield Neighbors
$426 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (19 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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House Lake View East
$1,013 per night
House ∙ 16 guests ∙ 5 bedrooms
4.9
"Excellent" (26 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment University Village / Little Italy
$138 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (307 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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Condo Near North
$213 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (22 ratings)
Near North, Chicago, Illinois, United States
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Apartment Logan Square
$109 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
4.6
"Outstanding" (41 ratings)
Logan Square, Chicago, Illinois, United States
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Aparthotel Near North
$191 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (185 ratings)
Near North, Chicago, Illinois, United States
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House Jefferson Park
$122 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (36 ratings)
Jefferson Park, Chicago, Illinois, United States
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Apartment North Center
$170 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (101 ratings)
North Center, Chicago, Illinois, United States
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Condo Ravenswood
$211 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (42 ratings)
Ravenswood, Chicago, Illinois, United States
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Apartment Chicago Loop
$148 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Chicago Loop, Chicago, Illinois, United States
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Apartment Near North
$352 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (82 ratings)
Near North, Chicago, Illinois, United States
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Apartment Chicago Loop
$155 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Chicago Loop, Chicago, Illinois, United States
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Apartment University Village / Little Italy
$217 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (66 ratings)
University Village / Little Italy, Chicago, Illinois, United States
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House Near West Side
$550 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
"Excellent" (17 ratings)
Near West Side, Chicago, Illinois, United States
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Apartment Near North
$266 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (22 ratings)
Near North, Chicago, Illinois, United States
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Apartment Near North
$271 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.9
"Excellent" (50 ratings)
Near North, Chicago, Illinois, United States
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Apartment Lake View East
$90 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.4
"Very good" (12 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Logan Square
$134 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (34 ratings)
Logan Square, Chicago, Illinois, United States
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Condo Wrightwood Neighbors
$199 per night
Condo ∙ 5 guests ∙ 5 bedrooms
4.6
"Outstanding" (30 ratings)
Wrightwood Neighbors, Chicago, Illinois, United States
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House Wicker Park
$267 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (74 ratings)
Wicker Park, Chicago, Illinois, United States
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Apartment Rogers Park
$158 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (199 ratings)
Rogers Park, Chicago, Illinois, United States
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Apartment Humboldt Park
$143 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.5
"Outstanding" (49 ratings)
Humboldt Park, Chicago, Illinois, United States
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House West Loop
$835 per night
House ∙ 15 guests ∙ 4 bedrooms
5.0
"Excellent" (47 ratings)
West Loop, Chicago, Illinois, United States
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Apartment Sheffield Neighbors
$285 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (81 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Condo East Garfield Park
$203 per night
Condo ∙ 5 guests ∙ 2 bedrooms
East Garfield Park, Chicago, Illinois, United States
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Condo Roscoe Village
$177 per night
Condo ∙ 8 guests ∙ 4 bedrooms
4.5
"Outstanding" (12 ratings)
Roscoe Village, Chicago, Illinois, United States
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Aparthotel Near North
$836 per night
Aparthotel ∙ 8 guests ∙ 3 bedrooms
4.9
"Excellent" (142 ratings)
Near North, Chicago, Illinois, United States
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Apartment West Loop
$224 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
West Loop, Chicago, Illinois, United States
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Aparthotel Near North
$238 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (80 ratings)
Near North, Chicago, Illinois, United States
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House Lake View East
$437 per night
House ∙ 20 guests ∙ 6 bedrooms
5.0
"Excellent" (13 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Logan Square
$210 per night
Apartment ∙ 12 guests ∙ 4 bedrooms
5.0
"Excellent" (12 ratings)
Logan Square, Chicago, Illinois, United States
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Aparthotel Near North
$361 per night
Aparthotel ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (124 ratings)
Near North, Chicago, Illinois, United States
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Apartment Avondale
$94 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Avondale, Chicago, Illinois, United States
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Apartment Lake View
$337 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (58 ratings)
Lake View, 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 may, remember it's the most expensive period, with average prices of $478. However, prices of vacation houses and apartments are most competitive in january (1/13 - 1/20).

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 February, make sure to book soon, as 60% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is September.

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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