Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

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Choose from 11,133 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chicago

Discover vacation rentals with top-notch guest ratings

Condo River West
from $998 per night
Condo ∙ 20 guests ∙ 6 bedrooms
4.9
Outstanding(97 ratings)
River West, Chicago, Illinois, United States
Vrbo
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Condo Lake View East
from $525 per night
Condo ∙ 7 guests ∙ 3 bedrooms
4.7
Excellent(26 ratings)
Lake View East, Chicago, Illinois, United States
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Apartment Rush & Division
from $250 per night
Apartment ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(4 ratings)
Rush & Division, Chicago, Illinois, United States
Vrbo
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Pet-friendly rentals in Chicago

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

Apartment Logan Square
from $79 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
4.7
Excellent(7 ratings)
Logan Square, Chicago, Illinois, United States
Pet-friendly
Vrbo
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House Streeterville
from $108 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(1 rating)
Streeterville, Chicago, Illinois, United States
Pet-friendly
Vrbo
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House Edgewater Beach
from $341 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding(4 ratings)
Edgewater Beach, Chicago, Illinois, United States
Pet-friendly
Vrbo
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Vacation rentals with pool in Chicago

Discover best cabin and house rentals with pool in Chicago

Apartment Chicago Loop
from $622 per night
Apartment ∙ 12 guests ∙ 6 bedrooms
4.7
Excellent(23 ratings)
Chicago Loop, Chicago, Illinois, United States
Pool
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Condo Near North
from $210 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(22 ratings)
Near North, Chicago, Illinois, United States
Pool
Vrbo
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Apartment South Loop
from $333 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(63 ratings)
South Loop, Chicago, Illinois, United States
Pool
Vrbo
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Best vacation rental offers in Chicago

House Woodlawn
from $78 per night
House ∙ 5 guests ∙ 4 bedrooms
Woodlawn, Chicago, Illinois, United States
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Apartment Lake View East
from $396 per night
Apartment ∙ 20 guests ∙ 5 bedrooms
5.0
Outstanding(62 ratings)
Lake View East, Chicago, Illinois, United States
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Villa South Shore
from $356 per night
Villa ∙ 16 guests ∙ 3 bedrooms
South Shore, Chicago, Illinois, United States
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Apartment Fulton Market
from $388 per night
Apartment ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(26 ratings)
Fulton Market, Chicago, Illinois, United States
Vrbo
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Condo Roscoe Village
from $116 per night
Condo ∙ 10 guests ∙ 5 bedrooms
3.6
Good(50 ratings)
Roscoe Village, Chicago, Illinois, United States
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House Streeterville
from $363 per night
House ∙ 12 guests ∙ 3 bedrooms
Streeterville, Chicago, Illinois, United States
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Apartment Gold Coast
from $129 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(3 ratings)
Gold Coast, Chicago, Illinois, United States
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House Lake View East
from $610 per night
House ∙ 20 guests ∙ 3 bedrooms
4.9
Outstanding(101 ratings)
Lake View East, Chicago, Illinois, United States
Vrbo
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House West Humboldt Park
from $62 per night
House ∙ 4 guests ∙ 2 bedrooms
West Humboldt Park, Chicago, Illinois, United States
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House West Town
from $334 per night
House ∙ 14 guests ∙ 4 bedrooms
4.4
Very good(6 ratings)
West Town, Chicago, Illinois, United States
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House Goose Island
from $258 per night
House ∙ 14 guests ∙ 3 bedrooms
5.0
Outstanding(51 ratings)
Goose Island, Chicago, Illinois, United States
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Apartment Streeterville
from $371 per night
Apartment ∙ 6 guests ∙ 4 bedrooms
4.7
Excellent(27 ratings)
Streeterville, Chicago, Illinois, United States
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Apartment Portage Park
from $126 per night
Apartment ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(113 ratings)
Portage Park, Chicago, Illinois, United States
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House Chatham
from $221 per night
House ∙ 12 guests ∙ 5 bedrooms
Chatham, Chicago, Illinois, United States
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Apartment Near North
from $124 per night
Apartment ∙ 7 guests ∙ 2 bedrooms
3.6
Good(22 ratings)
Near North, Chicago, Illinois, United States
Vrbo
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House West Town
from $285 per night
House ∙ 13 guests ∙ 5 bedrooms
4.4
Very good(15 ratings)
West Town, Chicago, Illinois, United States
Vrbo
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House Old Town
from $940 per night
House ∙ 12 guests ∙ 7 bedrooms
5.0
Outstanding(70 ratings)
Old Town, Chicago, Illinois, United States
Vrbo
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Apartment Near North Side
from $315 per night
Apartment ∙ 11 guests ∙ 3 bedrooms
4.5
Excellent(40 ratings)
Near North Side, Chicago, Illinois, United States
Vrbo
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Condo South Shore
from $126 per night
Condo ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(2 ratings)
South Shore, Chicago, Illinois, United States
Vrbo
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House Lincoln Park
from $427 per night
House ∙ 24 guests ∙ 4 bedrooms
5.0
Outstanding(190 ratings)
Lincoln Park, Chicago, Illinois, United States
Vrbo
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Apartment West Loop
from $148 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
4.3
Very good(26 ratings)
West Loop, Chicago, Illinois, United States
Vrbo
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House Fifth City
from $144 per night
House ∙ 5 guests ∙ 3 bedrooms
4.9
Outstanding(18 ratings)
Fifth City, Chicago, Illinois, United States
Vrbo
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Apartment Washington Park
from $72 per night
Apartment ∙ 3 guests ∙ 3 bedrooms
Washington Park, Chicago, Illinois, United States
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House West Loop
from $240 per night
House ∙ 9 guests ∙ 3 bedrooms
4.6
Excellent(71 ratings)
West Loop, Chicago, Illinois, United States
Vrbo
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House Lake View
from $617 per night
House ∙ 13 guests ∙ 4 bedrooms
5.0
Outstanding(5 ratings)
Lake View, Chicago, Illinois, United States
Vrbo
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House East Village
from $599 per night
House ∙ 12 guests ∙ 5 bedrooms
4.9
Outstanding(29 ratings)
East Village, Chicago, Illinois, United States
Vrbo
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Apartment Near North
from $229 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Near North, Chicago, Illinois, United States
Vrbo
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Condo Rogers Park
from $222 per night
Condo ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(242 ratings)
Rogers Park, Chicago, Illinois, United States
Vrbo
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House Near North
from $611 per night
House ∙ 16 guests ∙ 4 bedrooms
5.0
Outstanding(2 ratings)
Near North, Chicago, Illinois, United States
Vrbo
View deal
House Noble Square
from $690 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding(98 ratings)
Noble Square, Chicago, Illinois, United States
Vrbo
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Show all 10336 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 october, remember it's the most expensive period, with average prices of $730. However, prices of vacation houses and apartments are most competitive in january (1/24 – 1/31).

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 December, make sure to book soon, as 92% 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.

5,826,062 reviews
5,826,062 travelers who stayed in Chicago rated their vacation home 4.3/5 stars on average.

And we love our apartments

139 m² House
214 m² Apartment
204 m² Villa
232 m² Apartment
Condo
Show all 10336 apartments in Chicago

Features of Chicago vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 2,515 rentals
🌙 Minimum price starting at $60
🐾 Pet friendly vacation homes 4,645 rentals
🏡 Rentals available 11,069 rentals

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