Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

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Choose from 5,593 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chicago

Discover vacation rentals with top-notch guest ratings

Bed and breakfast Old Town
from $263 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with terrace | City view

5.0
Outstanding(521 ratings)
Old Town, Chicago, Illinois, United States
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Bed and breakfast Magnolia Glen
from $899 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

B&B with yard, patio & grill | City view | Good for workation

4.6
Excellent(505 ratings)
Magnolia Glen, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $199 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented spacious B&B with patio & yard | Good for workation | Pets allowed

4.9
Outstanding(401 ratings)
Bucktown, 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 $1,107 per night
Bed and breakfast ∙ 12 guests ∙ 5 bedrooms

B&B with 5 bedrooms for 12 persons

Boystown, Chicago, Illinois, United States
Pet-friendly
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Bed and breakfast Bucktown
from $198 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Bed and breakfast with garden & terrace | Good for workation

4.9
Outstanding(401 ratings)
Bucktown, Chicago, Illinois, United States
Pet-friendly
View deal
Bed and breakfast Bucktown
from $197 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

B&B with terrace & garden

4.9
Outstanding(401 ratings)
Bucktown, Chicago, Illinois, United States
Pet-friendly
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Best vacation rental offers in Chicago

Motel Rogers Park
from $147 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

3.5
Good(6 ratings)
Rogers Park, Chicago, Illinois, United States
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Bed and breakfast Magnolia Glen
from $197 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Lovely bed and breakfast with patio, barbeque & garden | City view | Perfect for remote work

4.6
Excellent(505 ratings)
Magnolia Glen, Chicago, Illinois, United States
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Bed and breakfast Fulton Market
from $367 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant bed and breakfast for 2 persons

4.9
Outstanding(208 ratings)
Fulton Market, Chicago, Illinois, United States
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Motel River North
from $221 per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel | Near Magnificent Mile

4.5
Excellent(1124 ratings)
River North, Chicago, Illinois, United States
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Motel Peterson Park
from $90 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.3
(797 ratings)
Peterson Park, Chicago, Illinois, United States
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Bed and breakfast Roscoe Village
from $380 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Family-oriented charming B&B with patio & yard

4.9
Outstanding(110 ratings)
Roscoe Village, Chicago, Illinois, United States
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Motel Washington Heights
from $85 per night
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel for 2 persons

3.7
Good(352 ratings)
Washington Heights, Chicago, Illinois, United States
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Bed and breakfast Bucktown
from $201 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

Family-friendly B&B with garden & terrace | Perfect for remote work | Dogs allowed

4.9
Outstanding(401 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from $283 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with garden

4.5
Excellent(266 ratings)
Wicker Park, Chicago, Illinois, United States
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Motel North Park
from $93 per night
Motel ∙ 2 guests ∙ 1 bedroom

Wonderful motel for 2 persons

3.6
Good(829 ratings)
North Park, Chicago, Illinois, United States
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Motel Archer Heights
from $136 per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

3.1
(1021 ratings)
Archer Heights, Chicago, Illinois, United States
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Bed and breakfast East Village
from $3,380 per night
Bed and breakfast ∙ 16 guests ∙ 8 bedrooms

B&B with garden | Perfect for remote work

East Village, Chicago, Illinois, United States
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Bed and breakfast Humboldt Park
from $415 per night
Bed and breakfast ∙ 7 guests ∙ 3 bedrooms

Bed and breakfast | Perfect for remote work

Humboldt Park, Chicago, Illinois, United States
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Bed and breakfast Old Town
from $588 per night
Bed and breakfast ∙ 10 guests ∙ 1 bedroom

Bed and breakfast with terrace | City view

5.0
Outstanding(521 ratings)
Old Town, Chicago, Illinois, United States
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Motel Rogers Park
from $157 per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel with fast internet

3.5
Good(6 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
Bed and breakfast Sheffield & DePaul
from $377 per night
Bed and breakfast ∙ 5 guests ∙ 1 bedroom

B&B with barbeque, yard & terrace | Perfect for remote work

4.7
Excellent(120 ratings)
Sheffield & DePaul, Chicago, Illinois, United States
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Bed and breakfast Fulton Market
from $256 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Pleasant B&B for 2 persons

4.9
Outstanding(208 ratings)
Fulton Market, Chicago, Illinois, United States
View deal
Bed and breakfast Magnolia Glen
from $240 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with grill, garden & patio | City view | Good for workation

4.6
Excellent(505 ratings)
Magnolia Glen, Chicago, Illinois, United States
View deal
Motel River North
from $220 per night
Motel ∙ 2 guests ∙ 1 bedroom

Pleasant motel | Close to Magnificent Mile

4.5
Excellent(1124 ratings)
River North, Chicago, Illinois, United States
View deal
Bed and breakfast Bucktown
from $201 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with patio & garden

4.9
Outstanding(401 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from $259 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with yard

4.5
Excellent(266 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Motel North Park
from $93 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.6
Good(829 ratings)
North Park, Chicago, Illinois, United States
View deal
Motel Archer Heights
from $126 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.1
(1021 ratings)
Archer Heights, Chicago, Illinois, United States
View deal
Motel Peterson Park
from $89 per night
Motel ∙ 2 guests ∙ 1 bedroom

Nice motel for 2 persons

3.3
(797 ratings)
Peterson Park, Chicago, Illinois, United States
View deal
Bed and breakfast Old Town
from $216 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with terrace

5.0
Outstanding(521 ratings)
Old Town, Chicago, Illinois, United States
View deal
Bed and breakfast Sheffield & DePaul
from $341 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Nice bed & breakfast with terrace, barbeque & yard | Good for workation

4.7
Excellent(120 ratings)
Sheffield & DePaul, Chicago, Illinois, United States
View deal
Motel Rogers Park
from $147 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel with fast internet | Close to the beach

3.5
Good(6 ratings)
Rogers Park, Chicago, Illinois, United States
View deal
Bed and breakfast Bucktown
from $201 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with terrace & garden

4.9
Outstanding(401 ratings)
Bucktown, Chicago, Illinois, United States
View deal
Bed and breakfast Wicker Park
from $283 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B with garden

4.5
Excellent(266 ratings)
Wicker Park, Chicago, Illinois, United States
View deal
Bed and breakfast Fulton Market
from $321 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast for 2 persons

4.9
Outstanding(208 ratings)
Fulton Market, Chicago, Illinois, United States
View deal
Show all 6023 apartments in Chicago

Price and Availability Index in Chicago

Click on any bar to see price and availability information

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 august, remember it's the most expensive period, with average prices of $575. However, prices of vacation houses and apartments are most competitive in december (12/12 – 12/19).

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 April, make sure to book soon, as 99% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is July.

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

Motel with fast internet | Close to the beach
Lovely bed and breakfast with patio, barbeque & garden | City view | Perfect for remote work
Pleasant bed and breakfast for 2 persons
Motel | Near Magnificent Mile
Motel for 2 persons
Show all 6023 apartments in Chicago

Features of Chicago vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 1,759 rentals
🌙 Minimum price starting at $82
🐾 Pet friendly vacation homes 2,399 rentals
🏡 Rentals available 5,593 rentals

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