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 Sheffield Neighbors
from $241 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 Kenwood
from $81 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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Bed and breakfast Magnolia Glen
from $159 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

House 5863- Bed and Breakfast - Adults Only

4.9
Outstanding
Magnolia Glen, 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

Bed and breakfast Boystown
from $765 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 $214 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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Bed and breakfast Bucktown
from $219 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 $271 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 $310 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 Legends South
from $44 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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Motel River North
from $110 per night
Motel ∙ 127 guests ∙ 1 bedroom

Ohio House Motel

River North, Chicago, Illinois, United States
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Bed and breakfast North Center
from $303 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Lyons' Suite

North Center, Chicago, Illinois, United States
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Bed and breakfast West Woodlawn
from $82 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 Avondale
from $162 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Prime Avondale

Avondale, Chicago, Illinois, United States
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Bed and breakfast Rogers Park
from $89 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

Farwell dream

3.4
Rogers Park, Chicago, Illinois, United States
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Bed and breakfast Sheffield & DePaul
from $317 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 West Woodlawn
from $83 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Chateau de Woodlawn - Room I - La Tour Eiffel

West Woodlawn, Chicago, Illinois, United States
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Bed and breakfast Englewood
from $66 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Simplified Living Space

Englewood, Chicago, Illinois, United States
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Bed and breakfast West Ridge
from $152 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Olive House

West Ridge, Chicago, Illinois, United States
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Bed and breakfast South Austin
from $132 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 $219 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(158 ratings)
Roscoe Village, Chicago, Illinois, United States
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Bed and breakfast Illinois Medical District
from $204 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Stylish Shared Condo Minutes from Downtown Chicago, 1Bedroom and Shared access

Illinois Medical District, Chicago, Illinois, United States
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Bed and breakfast West Woodlawn
from $83 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Afrique Francaise de Woodlawn 1

West Woodlawn, Chicago, Illinois, United States
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Bed and breakfast Roscoe Village
from $395 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Unique Chicago Penthouse Loft - Amazing Deal & Location

4.9
Outstanding(105 ratings)
Roscoe Village, Chicago, Illinois, United States
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Bed and breakfast Hyde Park
from $145 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Private room with private full bathroom

Hyde Park, Chicago, Illinois, United States
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Bed and breakfast Andersonville
from $85 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Hollywood Rentals LLC

3.6
Good
Andersonville, Chicago, Illinois, United States
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Bed and breakfast Bronzeville
from $101 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Hyde Park Modern Private Room - Near Univ of Chicago

Bronzeville, Chicago, Illinois, United States
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Bed and breakfast North Center
from $306 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Lyons' Den

North Center, Chicago, Illinois, United States
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Bed and breakfast University Village / Little Italy
from $230 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 Wicker Park
from $302 per night
Bed and breakfast ∙ 6 guests ∙ 1 bedroom

Wicker Park Inn

4.8
Outstanding
Wicker Park, Chicago, Illinois, United States
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Bed and breakfast Illinois Medical District
from $142 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Modern Shared Condo Near Downtown Chicago, Flexible Room Options and Shared Amenities

Illinois Medical District, Chicago, Illinois, United States
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Bed and breakfast Magnolia Glen
from $183 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Magnolia Studios

5.0
Outstanding
Magnolia Glen, Chicago, Illinois, United States
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Bed and breakfast Sheffield Neighbors
from $214 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 West Woodlawn
from $87 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 Sheffield Neighbors
from $268 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 $241 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 Sheffield Neighbors
from $450 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 Canaryville
from $60 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Close to Downtown - Free Parking

Canaryville, Chicago, Illinois, United States
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Motel River North
from $104 per night
Motel ∙ 4 guests ∙ 1 bedroom

Ohio House Motel

4.6
Excellent
River North, Chicago, Illinois, United States
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Show all 5162 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

5430 Happy Home
Ohio House Motel
Lyons' Suite
Afrique Francaise de Woodlawn 2
Prime Avondale
Show all 5162 apartments in Chicago

Features of Chicago vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 1,783 rentals
🌙 Minimum price starting at $44
🐾 Pet friendly vacation homes 2,248 rentals
🏡 Rentals available 5,512 rentals

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