Accommodation in Chicago

Chicago
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Top 50 Apartments in Chicago

440 ft² Apartment
from $62
10.0 "Excellent" (7 reviews)
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440 ft² Apartment

Irving Woods, Chicago, Illinois, United States
Apartment
2 guests
800 ft² Apartment
from $57
8.9 "Outstanding" (17 reviews)
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800 ft² Apartment

Albany Park, Chicago, Illinois, United States
Apartment
2 guests
1040 ft² Apartment
from $162
9.8 "Excellent" (75 reviews)
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1040 ft² Apartment

Near North, Chicago, Illinois, United States
Apartment
4 guests
2500 ft² Apartment
from $333
9.1 "Excellent" (14 reviews)
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2500 ft² Apartment

Old Town, Chicago, Illinois, United States
Apartment
4 guests
Apartment
from $54
9.2 "Excellent" (13 reviews)
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Apartment

Edgewater, Chicago, Illinois, United States
Apartment
2 guests
1000 ft² Apartment
from $84
9.0 "Excellent" (21 reviews)
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1000 ft² Apartment

Andersonville, Chicago, Illinois, United States
Apartment
3 guests
420 ft² Apartment
from $98
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420 ft² Apartment

South Loop, Chicago, Illinois, United States
Apartment
2 guests
850 ft² Apartment
from $138
10.0 "Excellent" (43 reviews)
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850 ft² Apartment

Near North, Chicago, Illinois, United States
Apartment
4 guests
930 ft² House
from $144
10.0 "Excellent" (10 reviews)
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930 ft² House

Oakland, Chicago, Illinois, United States
House
3 guests
Art Filled Loft with WiFi
from $145US
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Art Filled Loft with WiFi

Chicago, United States
Apartment
3 guests / 2 bedrooms / 1300 ft²
With 2 bedrooms and a TV, this 121m² apartment is located in Chicago. Other facilities include air conditioning and breakfast.
7 people are interested in this property
Cool Flat in Ukrainian Village
from $100US
9 Great (4 reviews)
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Cool Flat in Ukrainian Village

Chicago, United States
Apartment
4 guests / 2 bedrooms / 600 ft²
This apartment, offering air conditioning, is located in Chicago . Also providing a gym and breakfast, the 2-bedroom property has 60m² of space.
8 people are interested in this property
LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB 2. City & McCormick Place & safe
from $210US
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LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB 2. City & McCormick Place & safe

Chicago, United States
Apartment
6 guests / 2 bedrooms / 1100 ft²
This 2-bedroom apartment in Chicago offers 121m² of space. Amenities include air conditioning, a TV and parking.
9 people are interested in this property
Arkadia Tower One Bedroom
from $310US
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Arkadia Tower One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 902 ft²
Location! Parking Close Two Downtown
Flexible Cancellation
from $150US
10 Excellent (1 review)
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Location! Parking Close Two Downtown

Chicago, United States
Apartment
6 guests / 2 bedrooms / 900 ft²
River View Jr. One Bedroom
Flexible Cancellation
from $310US
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River View Jr. One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 539 ft²
Beautiful House by Lake and Nightlife
from $795US
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Beautiful House by Lake and Nightlife

Chicago, United States
House
14 guests / 5 bedrooms / 4000 ft²
All-Inclusive Furnished Jr. One Bedroom
from $310US
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All-Inclusive Furnished Jr. One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 662 ft²
LINEA All-Inclusive Jr. One Bedroom
Flexible Cancellation
from $310US
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LINEA All-Inclusive Jr. One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 601 ft²
River View All Inclusive Studio
from $310US
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River View All Inclusive Studio

Chicago, United States
Apartment
2 guests / 1 bedroom / 539 ft²
Arkadia Tower Studio
from $310US
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Arkadia Tower Studio

Chicago, United States
Apartment
2 guests / 1 bedroom / 510 ft²
River North Studio
Flexible Cancellation
from $310US
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River North Studio

Chicago, United States
Apartment
4 guests / 1 bedroom / 653 ft²
River North One Bedroom
from $310US
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River North One Bedroom

Chicago, United States
Apartment
5 guests / 1 bedroom / 961 ft²
River North Jr. One Bedroom
from $310US
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River North Jr. One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 660 ft²
River View One Bedroom
from $310US
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River View One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 637 ft²
All-Inclusive Furnished One Bedroom
from $310US
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All-Inclusive Furnished One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 751 ft²
LINEA All-Inclusive One Bedroom
Flexible Cancellation
from $310US
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LINEA All-Inclusive One Bedroom

Chicago, United States
Apartment
4 guests / 1 bedroom / 700 ft²
Wicker Park two Bedroom one Bathroom IIR
Flexible Cancellation
from $200US
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Wicker Park two Bedroom one Bathroom IIR

Chicago, United States
Apartment
5 guests / 2 bedrooms / 900 m²
The Dickens Place Trendy Flat
from $147US
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The Dickens Place Trendy Flat

Chicago, United States
Apartment
12 guests / 2 bedrooms / 1000 ft²
LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB. 1 FL. Close to Everything & safe
from $210US
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LUXURY & HUGE DISCOUNTS GREAT REVIEWS HOT TUB. 1 FL. Close to Everything & safe

Chicago, United States
Apartment
6 guests / 3 bedrooms / 1100 ft²
Located in Chicago, this 1300m² apartment offers 3 bedrooms and parking - a hot tub and a kitchen are also provided.
11 people are interested in this property
PRIVATE GUEST SUITE WIFI NETFLIX
from $175US
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PRIVATE GUEST SUITE WIFI NETFLIX

Chicago, United States
Apartment
3 guests / 1 bedroom / 430 ft²
Bright and Spacious Private Room & Bath
from $109US
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Bright and Spacious Private Room & Bath

Chicago, United States
Private room
2 guests / 1 bedroom / 900 ft²
Old Town Private Guest House Parking
Flexible Cancellation
from $129US
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Old Town Private Guest House Parking

Chicago, United States
Apartment
2 guests / 1 bedroom / 600 ft²
View all 1496 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.

Ready to book?

Our Apartments have an average score of 9/10! See what our guests are saying:

10 Excellent
September 2018
Even Cowgirls Get the Blues Room in Chicago! (Women Only)

The affordable room was well worth it. I had a small room to myself on the second floor. The second floor had common areas, including a kitchen and bathroom, shared by all the tenants and short-term guests. Our host, Dianna, set clear st...

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10 Excellent
August 2018
Florence Comfy Room! Retreat to RELAX!!! (Women Only)

Host is very accommodating. Thank you Dianna.

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10 Excellent
July 2018
Ukrainian Village Cool Flat II

Thanks to Layne and her Cool Flat II I had the best time in Chicago. Stayed for almost three months and I really felt like being part of the city. The flat is situated at the perfect location. Close to all exciting things to do in Ukrai...

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10 Excellent
June 2018
Sunny Triple Room in Excellent Location

Justine is perfect! Polite and hospitable! All living conditions corresponded to the description. I was offered coffee and tea in unlimited quantities, as well as snacks. Also it was really close to the train (blue line) - 5 min walking....

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Wimdu is Europe's largest marketplace for private accommodation. With over 350,000 properties in more than 150 countries, you're sure to find the perfect place to stay.

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440 ft² Apartment
800 ft² Apartment
1040 ft² Apartment
2500 ft² Apartment
Apartment
1000 ft² Apartment
420 ft² Apartment
850 ft² Apartment
930 ft² House
View all 1496 apartments in Chicago