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Chicago Vacation Rentals

Chicago
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Chicago
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Best-rated vacation rentals in Chicago

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Apartment Near West Side
$257 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (16 ratings)
Near West Side, Chicago, Illinois, United States
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Condo West Loop
$222 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (14 ratings)
West Loop, Chicago, Illinois, United States
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Apartment Roscoe Village
$159 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (6 ratings)
Roscoe 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 Logan Square
$80 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
Logan Square, Chicago, Illinois, United States
Pet-friendly
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Condo Heart of Chicago
$86 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Heart of Chicago, Chicago, Illinois, United States
Pet-friendly
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Condo West Town
$269 per night
Condo ∙ 9 guests ∙ 2 bedrooms
5.0
Outstanding (205 ratings)
West Town, 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 West Town
$293 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
West Town, Chicago, Illinois, United States
Internet
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Apartment Grand Boulevard
$190 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.4
Very good (10 ratings)
Grand Boulevard, Chicago, Illinois, United States
Internet
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House Near West Side
$373 per night
House ∙ 12 guests ∙ 5 bedrooms
Near West Side, 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 Dearborn Park
$952 per night
Condo ∙ 12 guests ∙ 4 bedrooms
4.7
Excellent (6 ratings)
Dearborn Park, Chicago, Illinois, United States
Pool
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House Humboldt Park
$289 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (5 ratings)
Humboldt Park, Chicago, Illinois, United States
Pool
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Condo Near North
$213 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (21 ratings)
Near North, Chicago, Illinois, United States
Pool
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Best vacation rental offers in Chicago

House Humboldt Park
$79 per night
House ∙ 6 guests ∙ 2 bedrooms
4.0
Very good (10 ratings)
Humboldt Park, Chicago, Illinois, United States
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Apartment Humboldt Park
$123 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent (66 ratings)
Humboldt Park, Chicago, Illinois, United States
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Apartment Heart of Chicago
$273 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Heart of Chicago, Chicago, Illinois, United States
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Condo Lake View
$254 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Lake View, Chicago, Illinois, United States
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Condo Armour Square
$246 per night
Condo ∙ 7 guests ∙ 3 bedrooms
Armour Square, Chicago, Illinois, United States
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House Beverly
$277 per night
House ∙ 10 guests ∙ 4 bedrooms
3.3
(21 ratings)
Beverly, Chicago, Illinois, United States
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House Pullman
$166 per night
House ∙ 7 guests ∙ 4 bedrooms
4.6
Excellent (31 ratings)
Pullman, Chicago, Illinois, United States
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Apartment Heart of Chicago
$164 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.5
Excellent (19 ratings)
Heart of Chicago, Chicago, Illinois, United States
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House Palmer Square
$374 per night
House ∙ 10 guests ∙ 5 bedrooms
Palmer Square, Chicago, Illinois, United States
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House Douglas
$332 per night
House ∙ 11 guests ∙ 5 bedrooms
Douglas, Chicago, Illinois, United States
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Condo Roscoe Village
$208 per night
Condo ∙ 8 guests ∙ 4 bedrooms
3.7
Good (31 ratings)
Roscoe Village, Chicago, Illinois, United States
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House West Town
$189 per night
House ∙ 8 guests ∙ 3 bedrooms
3.7
Good (18 ratings)
West Town, Chicago, Illinois, United States
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Condo Lake View East
$261 per night
Condo ∙ 8 guests ∙ 4 bedrooms
Lake View East, Chicago, Illinois, United States
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Apartment Ukrainian Village
$207 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
Ukrainian Village, Chicago, Illinois, United States
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Apartment Pilsen
$218 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (15 ratings)
Pilsen, Chicago, Illinois, United States
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House West Town
$272 per night
House ∙ 10 guests ∙ 3 bedrooms
4.8
Outstanding (49 ratings)
West Town, Chicago, Illinois, United States
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Apartment Lake View
$186 per night
Apartment ∙ 12 guests ∙ 4 bedrooms
4.9
Outstanding (17 ratings)
Lake View, Chicago, Illinois, United States
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House West Town
$622 per night
House ∙ 15 guests ∙ 4 bedrooms
West Town, Chicago, Illinois, United States
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House Chatham
$193 per night
House ∙ 12 guests ∙ 5 bedrooms
Chatham, Chicago, Illinois, United States
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House North Austin
$309 per night
House ∙ 12 guests ∙ 4 bedrooms
North Austin, Chicago, Illinois, United States
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Apartment Streeterville
$327 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (46 ratings)
Streeterville, Chicago, Illinois, United States
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Apartment Park Manor
$110 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (7 ratings)
Park Manor, Chicago, Illinois, United States
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Apartment Ukrainian Village
$420 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (32 ratings)
Ukrainian Village, Chicago, Illinois, United States
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Apartment Heart of Chicago
$256 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Heart of Chicago, Chicago, Illinois, United States
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House Grand Boulevard
$274 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (6 ratings)
Grand Boulevard, Chicago, Illinois, United States
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House Avondale
$496 per night
House ∙ 14 guests ∙ 5 bedrooms
4.7
Excellent (52 ratings)
Avondale, Chicago, Illinois, United States
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House West Loop
$159 per night
House ∙ 9 guests ∙ 3 bedrooms
4.6
Excellent (59 ratings)
West Loop, Chicago, Illinois, United States
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House Bronzeville
$602 per night
House ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent (12 ratings)
Bronzeville, Chicago, Illinois, United States
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Apartment West Ridge
$62 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (1 rating)
West Ridge, Chicago, Illinois, United States
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Condo Rogers Park
$127 per night
Condo ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (223 ratings)
Rogers Park, Chicago, Illinois, United States
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House Lincoln Park
$339 per night
House ∙ 24 guests ∙ 4 bedrooms
5.0
Outstanding (166 ratings)
Lincoln Park, Chicago, Illinois, United States
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House West Town
$429 per night
House ∙ 12 guests ∙ 5 bedrooms
4.7
Excellent (11 ratings)
West Town, Chicago, Illinois, United States
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Apartment Old Town
$202 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (11 ratings)
Old Town, Chicago, Illinois, United States
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House Uptown
$1,036 per night
House ∙ 21 guests ∙ 6 bedrooms
5.0
Outstanding (146 ratings)
Uptown, Chicago, Illinois, United States
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House East Garfield Park
$285 per night
House ∙ 12 guests ∙ 5 bedrooms
4.8
Outstanding (8 ratings)
East Garfield Park, Chicago, Illinois, United States
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Apartment Illinois Medical District
$273 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.6
Excellent (58 ratings)
Illinois Medical District, Chicago, Illinois, United States
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House East Village
$267 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (65 ratings)
East Village, Chicago, Illinois, United States
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Apartment West Town
$210 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (30 ratings)
West Town, Chicago, Illinois, United States
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House Washington Park
$288 per night
House ∙ 12 guests ∙ 4 bedrooms
4.1
Very good (9 ratings)
Washington Park, Chicago, Illinois, United States
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Price and Availability Index in Chicago

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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 october, remember it's the most expensive period, with average prices of $683. However, prices of vacation houses and apartments are most competitive in january (1/25 – 2/1).

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 January, make sure to book soon, as 94% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is June.

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.

9 reviews
9 travelers who stayed in Chicago rated their vacation home 4.3/5 stars on average.

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