Accommodation in Chicago

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Top 50 Apartments in Chicago

1040 ft² Apartment
from $387
9.8 "Excellent" (86 reviews)
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1040 ft² Apartment

Near North, Chicago, Illinois, United States
Apartment
4 guests
This apartment, offering a gym, is located in Chicago . Also providing breakfast and Wi-Fi, the 2-bedroom property has 58m² of space.
Apartment
from $74
9.0 "Excellent" (4 reviews)
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Apartment

Hanson Park, Chicago, Illinois, United States
Apartment
4 guests
Apartment
from $159
7.0 "Good" (4 reviews)
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Apartment

Hermosa, Chicago, Illinois, United States
Apartment
4 guests
Offering Wi-Fi and a kitchen, this 45m² apartment has 1 bedroom. It is located in Chicago and has air conditioning.
1290 ft² Apartment
from $91
10.0 "Excellent" (2 reviews)
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1290 ft² Apartment

Logan Square, Chicago, Illinois, United States
Apartment
4 guests
House
from $140
9.4 "Excellent" (18 reviews)
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House

Logan Square, Chicago, Illinois, United States
House
4 guests
Located in Chicago, this 42m² room offers 3 bedrooms and a TV - parking and Wi-Fi are also provided.
House
from $46
8.0 "Very good" (2 reviews)
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House

South Austin, Chicago, Illinois, United States
House
2 guests
340 ft² House
from $129
9.7 "Excellent" (7 reviews)
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340 ft² House

Logan Square, Chicago, Illinois, United States
House
2 guests
680 ft² Apartment
from $240
8.5 "Outstanding" (4 reviews)
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680 ft² Apartment

South Loop, Chicago, Illinois, United States
Apartment
2 guests
Apartment
from $165
9.5 "Excellent" (71 reviews)
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Apartment

Ranch Triangle, Chicago, Illinois, United States
Apartment
2 guests
590 ft² Apartment
from $240
9.8 "Excellent" (45 reviews)
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590 ft² Apartment

Gold Coast, Chicago, Illinois, United States
Apartment
2 guests
With 2 bedrooms and a TV, this 121m² apartment is located in Chicago. Other facilities include air conditioning and breakfast.
930 ft² House
from $209
10.0 "Excellent" (10 reviews)
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930 ft² House

Oakland, Chicago, Illinois, United States
House
3 guests
This apartment, offering air conditioning, is located in Chicago . Also providing a gym and breakfast, the 2-bedroom property has 60m² of space.
Apartment
from $54
9.3 "Excellent" (15 reviews)
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Apartment

Edgewater, Chicago, Illinois, United States
Apartment
2 guests
This 2-bedroom apartment in Chicago offers 121m² of space. Amenities include air conditioning, a TV and parking.
Apartment
from $120
9.0 "Excellent"
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Apartment

Palmer Square, Chicago, Illinois, United States
Apartment
4 guests
440 ft² Apartment
from $241
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440 ft² Apartment

South Loop, Chicago, Illinois, United States
Apartment
2 guests
1000 ft² Apartment
from $142
10.0 "Excellent" (7 reviews)
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1000 ft² Apartment

Pilsen, Chicago, Illinois, United States
Apartment
4 guests
440 ft² Apartment
from $95
10.0 "Excellent"
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440 ft² Apartment

Uptown, Chicago, Illinois, United States
Apartment
3 guests
740 ft² Apartment
from $101
10.0 "Excellent" (7 reviews)
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740 ft² Apartment

Irving Woods, Chicago, Illinois, United States
Apartment
2 guests
1400 ft² Apartment
from $262
9.9 "Excellent" (48 reviews)
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1400 ft² Apartment

Andersonville, Chicago, Illinois, United States
Apartment
4 guests
1040 ft² Apartment
from $419
9.9 "Excellent" (328 reviews)
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1040 ft² Apartment

Near North, Chicago, Illinois, United States
Apartment
4 guests
800 ft² Apartment
from $78
8.7 "Outstanding" (20 reviews)
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800 ft² Apartment

Albany Park, Chicago, Illinois, United States
Apartment
2 guests
850 ft² Apartment
from $328
10.0 "Excellent" (45 reviews)
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850 ft² Apartment

Near North, Chicago, Illinois, United States
Apartment
4 guests
650 ft² House
from $183
9.9 "Excellent" (17 reviews)
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650 ft² House

Wrightwood Neighbors, Chicago, Illinois, United States
House
2 guests
1000 ft² Apartment
from $90
10.0 "Excellent"
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1000 ft² Apartment

Irving Park, Chicago, Illinois, United States
Apartment
4 guests
590 ft² Apartment
from $185
9.1 "Excellent" (7 reviews)
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590 ft² Apartment

Chicago Loop, Chicago, Illinois, United States
Apartment
3 guests
House
from $118
8.0 "Very good" (1 review)
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House

Grand Boulevard, Chicago, Illinois, United States
House
2 guests
1000 ft² Apartment
from $138
9.0 "Excellent" (21 reviews)
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1000 ft² Apartment

Andersonville, Chicago, Illinois, United States
Apartment
3 guests
680 ft² Apartment
from $261
10.0 "Excellent" (2 reviews)
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680 ft² Apartment

Roscoe Village, Chicago, Illinois, United States
Apartment
4 guests
Apartment
from $189
9.7 "Excellent" (32 reviews)
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Apartment

Heart of Chicago, Chicago, Illinois, United States
Apartment
4 guests
8610 ft² Apartment
from $136
6.8 (5 reviews)
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8610 ft² Apartment

Jefferson Park, Chicago, Illinois, United States
Apartment
5 guests
Located in Chicago, this 1300m² apartment offers 3 bedrooms and parking - a hot tub and a kitchen are also provided.
House
from
9.0 "Excellent"
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House

North Center, Chicago, Illinois, United States
House
4 guests
1000 ft² Apartment
from $215
9.7 "Excellent" (70 reviews)
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1000 ft² Apartment

Edgewater, Chicago, Illinois, United States
Apartment
4 guests
540 ft² Apartment
from $21
10.0 "Excellent" (1 review)
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540 ft² Apartment

Hyde Park, Chicago, Illinois, United States
Apartment
3 guests
800 ft² House
from $219
9.8 "Excellent" (75 reviews)
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800 ft² House

West Town, Chicago, Illinois, United States
House
4 guests
850 ft² Apartment
from $155
9.6 "Excellent" (57 reviews)
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850 ft² Apartment

Horner Park, Chicago, Illinois, United States
Apartment
4 guests
1210 ft² Apartment
from $397
9.7 "Excellent" (12 reviews)
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1210 ft² Apartment

West Loop, Chicago, Illinois, United States
Apartment
4 guests
440 ft² Apartment
from $258
8.8 "Outstanding" (8 reviews)
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440 ft² Apartment

South Loop, Chicago, Illinois, United States
Apartment
2 guests
House
from $185
8.8 "Outstanding" (5 reviews)
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House

South Shore, Chicago, Illinois, United States
House
6 guests
890 ft² Apartment
from $237
9.9 "Excellent" (62 reviews)
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890 ft² Apartment

Roscoe Village, Chicago, Illinois, United States
Apartment
4 guests
500 ft² Apartment
from $123
8.0 "Very good" (7 reviews)
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500 ft² Apartment

Sheridan Park, Chicago, Illinois, United States
Apartment
4 guests
680 ft² Apartment
from $240
9.2 "Excellent" (10 reviews)
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680 ft² Apartment

Near South Side, Chicago, Illinois, United States
Apartment
2 guests
1000 ft² Apartment
from $132
9.1 "Excellent" (7 reviews)
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1000 ft² Apartment

Mid-North District, Chicago, Illinois, United States
Apartment
4 guests
1190 ft² Apartment
from $201
10.0 "Excellent" (24 reviews)
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1190 ft² Apartment

Tri-Taylor, Chicago, Illinois, United States
Apartment
5 guests
440 ft² Apartment
from $369
10.0 "Excellent" (1 review)
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440 ft² Apartment

Chicago Loop, Chicago, Illinois, United States
Apartment
4 guests
590 ft² Apartment
from $542
9.5 "Excellent" (65 reviews)
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590 ft² Apartment

Gold Coast, Chicago, Illinois, United States
Apartment
2 guests
500 ft² House
from $515
10.0 "Excellent" (1 review)
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500 ft² House

Near North, Chicago, Illinois, United States
House
2 guests
Apartment
from $195
9.3 "Excellent" (9 reviews)
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Apartment

Heart of Italy, Chicago, Illinois, United States
Apartment
4 guests
Apartment
from $190
8.1 "Very good" (26 reviews)
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Apartment

Sheffield Neighbors, Chicago, Illinois, United States
Apartment
4 guests
Apartment
from $124
9.7 "Excellent" (45 reviews)
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Apartment

West Woodlawn, Chicago, Illinois, United States
Apartment
6 guests
460 ft² Apartment
from $340
9.5 "Excellent" (4 reviews)
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460 ft² Apartment

Goose Island, Chicago, Illinois, United States
Apartment
2 guests
540 ft² Apartment
from $136
10.0 "Excellent" (1 review)
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540 ft² Apartment

Humboldt Park, Chicago, Illinois, United States
Apartment
5 guests
700 ft² Apartment
from $230
9.4 "Excellent" (81 reviews)
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700 ft² Apartment

Gold Coast, Chicago, Illinois, United States
Apartment
2 guests
View all 2019 apartments in Chicago

Price and Availability Index in Chicago

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 july, remember it's the most expensive period, with average prices of $263. However, prices of vacation houses and apartments are most competitive in april (4/11 - 4/18).

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 March, make sure to book soon, as 49% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is May.

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.

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1040 ft² Apartment
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