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Chicago Vacation Rentals

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Choose from 8,994 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chicago

Discover vacation rentals with top-notch guest ratings

House West Loop
from $234 per night
House ∙ 9 guests ∙ 3 bedrooms
4.6
Excellent(65 ratings)
West Loop, Chicago, Illinois, United States
Vrbo
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Apartment Logan Square
from $88 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding(4 ratings)
Logan Square, Chicago, Illinois, United States
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Apartment South Shore
from $153 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding
South Shore, Chicago, Illinois, United States
Agoda
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Pet-friendly rentals in Chicago

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

House Avondale
from $528 per night
House ∙ 16 guests ∙ 8 bedrooms
4.5
Excellent(2 ratings)
Avondale, Chicago, Illinois, United States
Pet-friendly
Vrbo
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Apartment Streeterville
from $313 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(20 ratings)
Streeterville, Chicago, Illinois, United States
Pet-friendly
Vrbo
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House Humboldt Park
from $577 per night
House ∙ 16 guests ∙ 5 bedrooms
Humboldt Park, Chicago, Illinois, United States
Pet-friendly
Vrbo
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Accommodation with Internet in Chicago

Choose your ideal rental with Internet and WiFi in Chicago

House South Shore
from $161 per night
House ∙ 12 guests ∙ 5 bedrooms
South Shore, Chicago, Illinois, United States
Internet
Vrbo
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House Goose Island
from $126 per night
House ∙ 9 guests ∙ 2 bedrooms
4.0
Very good(2 ratings)
Goose Island, Chicago, Illinois, United States
Internet
Vrbo
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Apartment Near North
from $475 per night
Apartment ∙ 9 guests ∙ 3 bedrooms
Near North, Chicago, Illinois, United States
Internet
Agoda
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Vacation rentals with pool in Chicago

Discover best cabin and house rentals with pool in Chicago

Condo Near North
from $217 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(21 ratings)
Near North, Chicago, Illinois, United States
Pool
Vrbo
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House Palmer Square
from $427 per night
House ∙ 16 guests ∙ 4 bedrooms
4.7
Excellent(47 ratings)
Palmer Square, Chicago, Illinois, United States
Pool
Vrbo
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Apartment Central Station
from $159 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Central Station, Chicago, Illinois, United States
Pool
Vrbo
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Best vacation rental offers in Chicago

Apartment Irving Park East
from $61 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(4 ratings)
Irving Park East, Chicago, Illinois, United States
Vrbo
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Condo River West
from $962 per night
Condo ∙ 20 guests ∙ 5 bedrooms
5.0
Outstanding(86 ratings)
River West, Chicago, Illinois, United States
Vrbo
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House Grand Boulevard
from $380 per night
House ∙ 15 guests ∙ 6 bedrooms
4.3
Very good(9 ratings)
Grand Boulevard, Chicago, Illinois, United States
Vrbo
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Apartment Albany Park
from $111 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.7
Excellent(3 ratings)
Albany Park, Chicago, Illinois, United States
Vrbo
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Apartment Chicago Loop
from $95 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Chicago Loop, Chicago, Illinois, United States
Vrbo
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Apartment Belmont Central
from $111 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding(23 ratings)
Belmont Central, Chicago, Illinois, United States
Vrbo
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House Pilsen
from $206 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(4 ratings)
Pilsen, Chicago, Illinois, United States
Vrbo
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Apartment Uptown
from $88 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.3
Very good(10 ratings)
Uptown, Chicago, Illinois, United States
Vrbo
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Apartment Grant Park
from $579 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(10 ratings)
Grant Park, Chicago, Illinois, United States
Vrbo
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House Noble Square
from $598 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding(96 ratings)
Noble Square, Chicago, Illinois, United States
Vrbo
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Apartment Pulaski Park
from $126 per night
Apartment ∙ 9 guests ∙ 2 bedrooms
4.5
Excellent(13 ratings)
Pulaski Park, West Town, Chicago
Vrbo
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Apartment Bucktown
from $152 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(14 ratings)
Bucktown, Chicago, Illinois, United States
Vrbo
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Apartment Near North Side
from $161 per night
Apartment ∙ 11 guests ∙ 3 bedrooms
4.3
Very good(24 ratings)
Near North Side, Chicago, Illinois, United States
Vrbo
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Apartment Lake View
from $141 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(10 ratings)
Lake View, Chicago, Illinois, United States
Vrbo
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House Pocket Town
from $97 per night
House ∙ 8 guests ∙ 4 bedrooms
4.3
Very good(8 ratings)
Pocket Town, Chicago, Illinois, United States
Vrbo
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Apartment Wicker Park
from $121 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
Wicker Park, Chicago, Illinois, United States
Vrbo
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House Streeterville
from $316 per night
House ∙ 8 guests ∙ 2 bedrooms
3.0
(6 ratings)
Streeterville, Chicago, Illinois, United States
Vrbo
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House Bronzeville
from $579 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(18 ratings)
Bronzeville, Chicago, Illinois, United States
Vrbo
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Apartment Logan Square
from $184 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(7 ratings)
Logan Square, Chicago, Illinois, United States
Vrbo
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Apartment Douglas Park
from $120 per night
Apartment ∙ 3 guests ∙ 2 bedrooms
Douglas Park, Chicago, Illinois, United States
Vrbo
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Apartment Grand Crossing
from $199 per night
Apartment ∙ 7 guests ∙ 3 bedrooms
4.7
Excellent(11 ratings)
Grand Crossing, Chicago, Illinois, United States
Vrbo
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House Humboldt Park
from $55 per night
House ∙ 6 guests ∙ 2 bedrooms
4.2
Very good(29 ratings)
Humboldt Park, Chicago, Illinois, United States
Vrbo
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Condo Roscoe Village
from $166 per night
Condo ∙ 10 guests ∙ 4 bedrooms
3.6
Good(46 ratings)
Roscoe Village, Chicago, Illinois, United States
Vrbo
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House Douglas
from $170 per night
House ∙ 9 guests ∙ 4 bedrooms
4.0
Very good(26 ratings)
Douglas, Chicago, Illinois, United States
Vrbo
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Apartment Chicago Loop
from $154 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(10 ratings)
Chicago Loop, Chicago, Illinois, United States
Vrbo
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House Grand Boulevard
from $390 per night
House ∙ 10 guests ∙ 5 bedrooms
3.0
(2 ratings)
Grand Boulevard, Chicago, Illinois, United States
Vrbo
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House North Lawndale
from $244 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding(6 ratings)
North Lawndale, Chicago, Illinois, United States
Vrbo
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Condo Lake View
from $232 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Lake View, Chicago, Illinois, United States
Vrbo
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House Wicker Park
from $484 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding(1 rating)
Wicker Park, Chicago, Illinois, United States
Vrbo
View deal
House West Town
from $443 per night
House ∙ 10 guests ∙ 5 bedrooms
West Town, Chicago, Illinois, United States
Vrbo
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Apartment Streeterville
from $200 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent(36 ratings)
Streeterville, Chicago, Illinois, United States
Vrbo
View deal
House Pullman
from $170 per night
House ∙ 7 guests ∙ 4 bedrooms
4.6
Excellent(30 ratings)
Pullman, Chicago, Illinois, United States
Vrbo
View deal
Apartment Near North Side
from $130 per night
Apartment ∙ 10 guests ∙ 2 bedrooms
5.0
Outstanding(12 ratings)
Near North Side, Chicago, Illinois, United States
Vrbo
View deal
Apartment West Loop
from $310 per night
Apartment ∙ 12 guests ∙ 3 bedrooms
4.8
Outstanding(44 ratings)
West Loop, Chicago, Illinois, United States
Vrbo
View deal
Condo Lincoln Park
from $211 per night
Condo ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(33 ratings)
Lincoln Park, Chicago, Illinois, United States
Vrbo
View deal
House Auburn Gresham
from $468 per night
House ∙ 18 guests ∙ 5 bedrooms
5.0
Outstanding(1 rating)
Auburn Gresham, Chicago, Illinois, United States
Vrbo
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Condo Wicker Park
from $503 per night
Condo ∙ 14 guests ∙ 7 bedrooms
4.9
Outstanding(17 ratings)
Wicker Park, Chicago, Illinois, United States
Vrbo
View deal
Condo South Shore
from $126 per night
Condo ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(1 rating)
South Shore, Chicago, Illinois, United States
Vrbo
View deal
Apartment Near North
from $233 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
Near North, Chicago, Illinois, United States
Vrbo
View deal
View all 8867 apartments in Chicago

Price and Availability Index in Chicago

Click on any bar to see price and availability information

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 august, remember it's the most expensive period, with average prices of $601. However, prices of vacation houses and apartments are most competitive in february (2/1 – 2/8).

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 September, make sure to book soon, as 93% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is October.

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 4.4/5 stars on average.

And we love our apartments

74 m² Apartment
520 m² Condo
335 m² House
Apartment
63 m² Apartment
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Features of Chicago vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 2,277 rentals
🌙 Minimum price starting at $56
🐾 Pet friendly vacation homes 4,062 rentals
🏡 Rentals available 8,994 rentals

Chicago: other vacation ideas

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