Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

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Best-rated vacation rentals in Chicago

Discover vacation rentals with top-notch guest ratings

Bed and breakfast Bucktown
from $197 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Cuckoo Room (Second Floor)

4.9
Outstanding(341 ratings)
Bucktown, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $310 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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Bed and breakfast Kenwood
from $71 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Drexel Apartments, Downtown Hyde Park

4.6
Excellent
Kenwood, 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 $102 per night
Resort ∙ 127 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 $716 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 $225 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

Ray's Bucktown Bed and Breakfast

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 $281 per night
Resort ∙ 127 guests ∙ 1 bedroom

The Hotel at Midtown

4.5
Excellent
Bucktown, Chicago, Illinois, United States
Pool
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Resort Bucktown
from $323 per night
2 guests ∙ 1 bedroom

Resort

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

Bed and breakfast Sheffield Neighbors
from $337 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 Sheffield Neighbors
from $405 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 Sheffield Neighbors
from $376 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 Back of the Yards
from $54 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Beautiful Home Near Downtwon - Free Parking!

Back of the Yards, Chicago, Illinois, United States
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Bed and breakfast West Woodlawn
from $80 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chateau de Woodlawn - Room II - Le Parisienne

West Woodlawn, Chicago, Illinois, United States
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Bed and breakfast Bridgeport
from $305 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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Bed and breakfast Roscoe Village
from $320 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Unique Chicago Penthouse Loft - Amazing Deal & Location

4.9
Outstanding(108 ratings)
Roscoe Village, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $228 per night
Bed and breakfast ∙ 10 guests ∙ 1 bedroom

Wicker Park Inn

4.8
Outstanding
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast University Village / Little Italy
from $145 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Shared Modern apartment close to Downtown Chicago

University Village / Little Italy, Chicago, Illinois, United States
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Bed and breakfast Douglas
from $147 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Villa Dubois Guest Room 6

Douglas, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $225 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 Old Town
from $212 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

The Sono Chicago

4.8
Outstanding
Old Town, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $260 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Hoyne)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast Wicker Park
from $237 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Room, 1 King Bed (Pierce)

4.5
Excellent(240 ratings)
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast Legends South
from $54 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

5430 Happy Home

4.3
Very good
Legends South, Chicago, Illinois, United States
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Bed and breakfast Back of the Yards
from $54 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wonderful Home Close to Downtown Chicago - Free Parking

Back of the Yards, Chicago, Illinois, United States
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Bed and breakfast Sheffield & DePaul
from $277 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 South Austin
from $135 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

A Hidden Gem, approx 15 mins to downtown Chicago!

South Austin, Chicago, Illinois, United States
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Bed and breakfast Roscoe Village
from $212 per night
Bed and breakfast ∙ 6 guests ∙ 2 bedrooms

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

4.9
Outstanding(162 ratings)
Roscoe Village, Chicago, Illinois, United States
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Motel Washington Heights
from $75 per night
2 guests ∙ 1 bedroom

Motel

Washington Heights, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $337 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 West Woodlawn
from $92 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Afrique Francaise de Woodlawn 2

West Woodlawn, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $202 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 Sheffield Neighbors
from $244 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 Sheffield Neighbors
from $307 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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Motel River North
from $106 per night
Motel ∙ 4 guests ∙ 1 bedroom

Ohio House Motel

4.5
Excellent
River North, Chicago, Illinois, United States
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Bed and breakfast Boystown
from $73 per night
Bed and breakfast ∙ 12 guests ∙ 1 bedroom

Dorothy's

Boystown, Chicago, Illinois, United States
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Bed and breakfast West Loop
from $269 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 West Loop
from $314 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 $269 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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Show all 5182 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

Florencia Suite
Grand Tuscan Suite
Milan Suite
Beautiful Home Near Downtwon - Free Parking!
Chateau de Woodlawn - Room II - Le Parisienne
Show all 5182 apartments in Chicago

Features of Chicago vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 1,728 rentals
🌙 Minimum price starting at $54
🐾 Pet friendly vacation homes 2,255 rentals
🏡 Rentals available 5,455 rentals

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