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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

House Washington Park
$352 per night
House ∙ 8 guests ∙ 3 bedrooms
Washington Park, Chicago, Illinois, United States
Pet-friendly
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House West Town
$183 per night
House ∙ 8 guests ∙ 3 bedrooms
4.5
Excellent (14 ratings)
West Town, Chicago, Illinois, United States
Pet-friendly
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Apartment South Chicago
$87 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.5
Excellent (4 ratings)
South Chicago, 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 Irving Park East
$51 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (4 ratings)
Irving Park East, Chicago, Illinois, United States
Internet
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Apartment Washington Park
$103 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Washington Park, Chicago, Illinois, United States
Internet
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Apartment Heart of Chicago
$118 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (50 ratings)
Heart of Chicago, 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
$199 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (19 ratings)
Near North, Chicago, Illinois, United States
Pool
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Aparthotel Near North
$549 per night
Aparthotel ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (147 ratings)
Near North, Chicago, Illinois, United States
Pool
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Condo Near North
$228 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (23 ratings)
Near North, Chicago, Illinois, United States
Pool
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Best vacation rental offers in Chicago

Apartment Ashburn
$97 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Ashburn, Chicago, Illinois, United States
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Condo The Gap
$95 per night
Condo ∙ 5 guests ∙ 2 bedrooms
3.6
Good (27 ratings)
The Gap, Chicago, Illinois, United States
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Apartment Heart of Chicago
$227 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (12 ratings)
Heart of Chicago, Chicago, Illinois, United States
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Apartment Rogers Park
$151 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rogers Park, Chicago, Illinois, United States
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Condo West Ridge
$208 per night
Condo ∙ 8 guests ∙ 3 bedrooms
4.1
Very good (15 ratings)
West Ridge, Chicago, Illinois, United States
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House Douglas
$200 per night
House ∙ 9 guests ∙ 4 bedrooms
3.9
Good (21 ratings)
Douglas, Chicago, Illinois, United States
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House Douglas
$211 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (9 ratings)
Douglas, Chicago, Illinois, United States
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House Logan Square
$435 per night
House ∙ 10 guests ∙ 5 bedrooms
3.8
Good (5 ratings)
Logan Square, Chicago, Illinois, United States
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Apartment Ukrainian Village
$286 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (5 ratings)
Ukrainian Village, Chicago, Illinois, United States
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Condo Logan Square
$696 per night
Condo ∙ 14 guests ∙ 7 bedrooms
4.4
Very good (3 ratings)
Logan Square, Chicago, Illinois, United States
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House North Lawndale
$224 per night
House ∙ 6 guests ∙ 3 bedrooms
North Lawndale, Chicago, Illinois, United States
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Apartment Greater Grand Crossing
$113 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Greater Grand Crossing, Chicago, Illinois, United States
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Apartment Logan Square
$108 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
4.6
Excellent (44 ratings)
Logan Square, Chicago, Illinois, United States
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Apartment Ukrainian Village
$271 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (5 ratings)
Ukrainian Village, Chicago, Illinois, United States
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House Homan Square
$156 per night
House ∙ 8 guests ∙ 3 bedrooms
4.4
Very good (144 ratings)
Homan Square, Chicago, Illinois, United States
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Apartment Goose Island
$801 per night
Apartment ∙ 16 guests ∙ 4 bedrooms
5.0
Outstanding (113 ratings)
Goose Island, Chicago, Illinois, United States
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Apartment Cragin
$96 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Cragin, Chicago, Illinois, United States
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House Ranch Triangle
$633 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (57 ratings)
Ranch Triangle, Chicago, Illinois, United States
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House Avondale
$758 per night
House ∙ 16 guests ∙ 6 bedrooms
4.9
Outstanding (62 ratings)
Avondale, Chicago, Illinois, United States
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Apartment Woodlawn
$212 per night
Apartment ∙ 10 guests ∙ 3 bedrooms
4.8
Outstanding (29 ratings)
Woodlawn, Chicago, Illinois, United States
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House Logan Square
$139 per night
House ∙ 10 guests ∙ 2 bedrooms
4.5
Excellent (187 ratings)
Logan Square, Chicago, Illinois, United States
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Apartment Belmont Central
$136 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (18 ratings)
Belmont Central, Chicago, Illinois, United States
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Condo Hyde Park
$279 per night
Condo ∙ 9 guests ∙ 4 bedrooms
4.6
Excellent (36 ratings)
Hyde Park, Chicago, Illinois, United States
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Apartment Near West Side
$145 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.7
Excellent (35 ratings)
Near West Side, Chicago, Illinois, United States
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House The Island
$129 per night
House ∙ 8 guests ∙ 3 bedrooms
4.5
Excellent (14 ratings)
The Island, Chicago, Illinois, United States
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Condo Lake View
$113 per night
Condo ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (3 ratings)
Lake View, Chicago, Illinois, United States
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House Avondale
$387 per night
House ∙ 14 guests ∙ 5 bedrooms
4.6
Excellent (47 ratings)
Avondale, Chicago, Illinois, United States
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House Fifth City
$217 per night
House ∙ 5 guests ∙ 3 bedrooms
4.9
Outstanding (7 ratings)
Fifth City, Chicago, Illinois, United States
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Apartment Lake View East
$113 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.4
Very good (9 ratings)
Lake View East, Chicago, Illinois, United States
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House Legends South
$367 per night
House ∙ 12 guests ∙ 4 bedrooms
4.5
Excellent (7 ratings)
Legends South, Chicago, Illinois, United States
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Apartment Logan Square
$58 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.7
Excellent (66 ratings)
Logan Square, Chicago, Illinois, United States
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House Mayfair
$187 per night
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding (103 ratings)
Mayfair, Chicago, Illinois, United States
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Apartment Park Manor
$105 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (3 ratings)
Park Manor, Chicago, Illinois, United States
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Condo South Loop
$273 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (25 ratings)
South Loop, Chicago, Illinois, United States
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Apartment West Town
$248 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (27 ratings)
West Town, Chicago, Illinois, United States
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House Grand Boulevard
$251 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Grand Boulevard, Chicago, Illinois, United States
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Apartment Near North
$301 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (12 ratings)
Near North, Chicago, Illinois, United States
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House Grand Boulevard
$557 per night
House ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent (9 ratings)
Grand Boulevard, Chicago, Illinois, United States
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Apartment Pulaski Park
$195 per night
Apartment ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent (22 ratings)
Pulaski Park, West Town, Chicago
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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 may, remember it's the most expensive period, with average prices of $538. However, prices of vacation houses and apartments are most competitive in february (2/3 - 2/10).

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 May, make sure to book soon, as 79% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is November.

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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