Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

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Choose from 5,559 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chicago

Discover vacation rentals with top-notch guest ratings

Bed and breakfast Magnolia Glen
from $148 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Junior Room (Room 2)

4.5
Excellent(472 ratings)
Magnolia Glen, Chicago, Illinois, United States
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Bed and breakfast Old Town
from $244 per night
Bed and breakfast ∙ 10 guests ∙ 1 bedroom

Premium Apartment

4.9
Outstanding(452 ratings)
Old Town, Chicago, Illinois, United States
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Bed and breakfast Old Town
from $155 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Superior Room, 2 Queen Beds

4.9
Outstanding(452 ratings)
Old Town, 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

Resort Archer Heights
from $105 per night
Resort ∙ 4 guests ∙ 1 bedroom

Carlton Inn Midway

3.4
Archer Heights, Chicago, Illinois, United States
Pet-friendly
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Bed and breakfast Boystown
from $1,070 per night
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

Five bedroom - 3 bath - Sleeps 12

Boystown, Chicago, Illinois, United States
Pet-friendly
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Bed and breakfast Bucktown
from $153 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Cuckoo Room (Second Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
Pet-friendly
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Vacation rentals with pool in Chicago

Discover best cabin and house rentals with pool in Chicago

Resort Bucktown
from $245 per night
10 guests ∙ 1 bedroom

Resort

Bucktown, Chicago, Illinois, United States
Pool
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Best vacation rental offers in Chicago

Bed and breakfast Sheffield & DePaul
from $250 per night
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

Villa D' Citta

3.8
Good
Sheffield & DePaul, Chicago, Illinois, United States
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Bed and breakfast Bridgeport
from $319 per night
Bed and breakfast ∙ 9 guests ∙ 3 bedrooms

The Polo Inn Bridgeport U. S.A.

5.0
Outstanding
Bridgeport, Chicago, Illinois, United States
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Motel River North
from $73 per night
Motel ∙ 5 guests ∙ 1 bedroom

Ohio House Motel

4.5
Excellent
River North, Chicago, Illinois, United States
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Bed and breakfast Boystown
from $47 per night
Bed and breakfast ∙ 12 guests ∙ 1 bedroom

Dorothy's

Boystown, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $216 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Euro Room

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast Roscoe Village
from $347 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Unique Chicago Penthouse Loft - Amazing Deal & Location

4.9
Outstanding(110 ratings)
Roscoe Village, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $271 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Capone's Cantina

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $338 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Grand Tuscan Suite

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $278 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Carmen)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $243 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Venetian Suite

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Motel Washington Heights
from $87 per night
2 guests ∙ 1 bedroom

Motel

Washington Heights, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $326 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Sinclair)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $243 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Caesar's Lair

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $215 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Meno)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $242 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Bellow)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $243 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Rooney)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $326 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Suite, 1 King Bed (Everleigh)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $280 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Harvey)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $216 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Concord)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $278 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Dybek)

4.9
Outstanding(166 ratings)
West Loop, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $165 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Eagles Nest (Second Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
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Motel Edgewater
from $103 per night
Motel ∙ 4 guests ∙ 1 bedroom

Heart O' Chicago Motel

3.8
Good
Edgewater, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $312 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Milan Suite

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $312 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Florencia Suite

4.6
Excellent(99 ratings)
Sheffield Neighbors, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $166 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chickadee room (First Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $166 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Woodpecker (Second Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $198 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 Queen Bed (Wabansia)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $294 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Exclusive Apartment, 1 Queen Bed with Sofa bed (Garden)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $162 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Flamingo Room (First Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $210 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Damen)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
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Show all 5891 apartments in Chicago

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.

7 reviews
7 travelers who stayed in Chicago rated their vacation home 4.1/5 stars on average.

And we love our apartments

Villa D' Citta
The Polo Inn Bridgeport U. S.A.
Ohio House Motel
Dorothy's
Euro Room
Show all 5891 apartments in Chicago

Features of Chicago vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 1,751 rentals
🌙 Minimum price starting at $47
🐾 Pet friendly vacation homes 2,369 rentals
🏡 Rentals available 5,559 rentals

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