Chicago Vacation Rentals - Wimdu base64Hash Chicago Vacation Rentals - Wimdu

Chicago Vacation Rentals

Chicago
Anytime
Guests
Chicago
Anytime
Guests
Find quality vacation rentals and city apartments!

Best-rated vacation rentals in Chicago

Discover vacation rentals with top-notch guest ratings

Apartment Humboldt Park
$120 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent (64 ratings)
Humboldt Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House West Loop
$156 per night
House ∙ 9 guests ∙ 3 bedrooms
4.6
Excellent (63 ratings)
West Loop, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Bed and breakfast Goose Island
$90 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding
Goose Island, Chicago, Illinois, United States
Details
Agoda
View deal
View deal

Pet-friendly rentals in Chicago

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

Apartment Logan Square
$108 per night
Apartment ∙ 4 guests ∙ 3 bedrooms
5.0
Outstanding (3 ratings)
Logan Square, Chicago, Illinois, United States
Pet-friendly
Details
Vrbo
View deal
View deal
Apartment South Austin
$71 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Austin, Chicago, Illinois, United States
Pet-friendly
Details
Vrbo
View deal
View deal
House Budlong Woods
$406 per night
House ∙ 9 guests ∙ 4 bedrooms
Budlong Woods, Chicago, Illinois, United States
Pet-friendly
Details
Agoda
View deal
View deal
See all pet-friendly offers

Accommodation with Internet in Chicago

Choose your ideal rental with Internet and WiFi in Chicago

Apartment Uptown
$64 per night
Apartment ∙ 5 guests ∙ 1 bedroom
Uptown, Chicago, Illinois, United States
Internet
Details
Agoda
View deal
View deal
House Humboldt Park
$72 per night
House ∙ 6 guests ∙ 2 bedrooms
4.2
Very good (18 ratings)
Humboldt Park, Chicago, Illinois, United States
Internet
Details
Vrbo
View deal
View deal
Apartment West Loop
$147 per night
Apartment ∙ 2 guests ∙ 1 bedroom
West Loop, Chicago, Illinois, United States
Internet
Details
HousingAnywhere
View deal
View deal
See all offers with internet

Vacation rentals with pool in Chicago

Discover best cabin and house rentals with pool in Chicago

Condo Near North
$206 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (21 ratings)
Near North, Chicago, Illinois, United States
Pool
Details
Vrbo
View deal
View deal
House Grand Boulevard
$632 per night
House ∙ 15 guests ∙ 6 bedrooms
Grand Boulevard, Chicago, Illinois, United States
Pool
Details
Agoda
View deal
View deal
House West Town
$603 per night
House ∙ 10 guests ∙ 5 bedrooms
West Town, Chicago, Illinois, United States
Pool
Details
Vrbo
View deal
View deal
See all offers with pool

Best vacation rental offers in Chicago

House Near North Side
$267 per night
House ∙ 11 guests ∙ 3 bedrooms
4.5
Excellent (2 ratings)
Near North Side, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment University Village / Little Italy
$189 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (163 ratings)
University Village / Little Italy, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Rogers Park
$183 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (34 ratings)
Rogers Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House West Town
$275 per night
House ∙ 10 guests ∙ 3 bedrooms
4.9
Outstanding (51 ratings)
West Town, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Pullman
$166 per night
House ∙ 7 guests ∙ 4 bedrooms
4.7
Excellent (27 ratings)
Pullman, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Bed and breakfast Rogers Park
$71 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
4.8
Outstanding
Rogers Park, Chicago, Illinois, United States
Details
Agoda
View deal
View deal
Condo West Loop
$277 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (16 ratings)
West Loop, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Lake View East
$155 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.9
Outstanding (12 ratings)
Lake View East, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Heart of Chicago
$168 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (97 ratings)
Heart of Chicago, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House West Town
$768 per night
House ∙ 16 guests ∙ 4 bedrooms
West Town, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Bucktown
$84 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Bucktown, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Woodlawn
$4 per night
Apartment ∙ 7 guests ∙ 4 bedrooms
Woodlawn, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Grand Boulevard
$204 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (8 ratings)
Grand Boulevard, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Condo South Shore
$141 per night
Condo ∙ 8 guests ∙ 4 bedrooms
South Shore, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Condo Roscoe Village
$167 per night
Condo ∙ 10 guests ∙ 4 bedrooms
3.7
Good (33 ratings)
Roscoe Village, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment West Loop
$147 per night
Apartment ∙ 2 guests ∙ 1 bedroom
West Loop, Chicago, Illinois, United States
Details
HousingAnywhere
View deal
View deal
Apartment Wicker Park
$112 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Wicker Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Avondale
$529 per night
House ∙ 14 guests ∙ 5 bedrooms
4.6
Excellent (52 ratings)
Avondale, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Big Oaks
$160 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (43 ratings)
Big Oaks, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Uptown
$1,024 per night
House ∙ 21 guests ∙ 6 bedrooms
5.0
Outstanding (145 ratings)
Uptown, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House South Shore
$275 per night
House ∙ 16 guests ∙ 3 bedrooms
5.0
Outstanding (13 ratings)
South Shore, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Portage Park
$96 per night
Apartment ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (102 ratings)
Portage Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Lincoln Park
$128 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Lincoln Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Condo Jackson Park
$90 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Jackson Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment South Austin
$120 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
4.0
Very good (2 ratings)
South Austin, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Condo Austin
$150 per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.6
Excellent (40 ratings)
Austin, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Condo Lake View
$282 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Lake View, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Grand Boulevard
$107 per night
Apartment ∙ 8 guests ∙ 2 bedrooms
4.9
Outstanding (93 ratings)
Grand Boulevard, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Bed and breakfast Park Boulevard
$79 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Park Boulevard, Chicago, Illinois, United States
Details
Agoda
View deal
View deal
House Bronzeville
$584 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding (13 ratings)
Bronzeville, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Irving Park East
$134 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (11 ratings)
Irving Park East, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Uptown
$132 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (43 ratings)
Uptown, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
House Chatham
$170 per night
House ∙ 5 guests ∙ 3 bedrooms
4.8
Outstanding (8 ratings)
Chatham, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Roscoe Village
$232 per night
Apartment ∙ 10 guests ∙ 1 bedroom
4.1
Very good
Roscoe Village, Chicago, Illinois, United States
Details
Agoda
View deal
View deal
Apartment West Loop
$152 per night
Apartment ∙ 2 guests ∙ 1 bedroom
West Loop, Chicago, Illinois, United States
Details
HousingAnywhere
View deal
View deal
Condo Hyde Park
$181 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Hyde Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Belmont Central
$105 per night
Apartment ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (23 ratings)
Belmont Central, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Condo Washington Park
$71 per night
Condo ∙ 2 guests ∙ 2 bedrooms
Washington Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
Apartment Brighton Park
$147 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.6
Excellent (18 ratings)
Brighton Park, Chicago, Illinois, United States
Details
Vrbo
View deal
View deal
View all 9147 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 october, remember it's the most expensive period, with average prices of $613. However, prices of vacation houses and apartments are most competitive in november (11/30 – 12/7).

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 95% of the vacation rentals have already been booked. In contrast, the month with the highest availability rate in Chicago is September.

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.

9 reviews
9 travelers who stayed in Chicago rated their vacation home 4.4/5 stars on average.

And we love our apartments

167 m² House
Apartment
102 m² Apartment
121 m² House
House
View all 9147 apartments in Chicago

Features of Chicago vacation rentals

💳 Discounts up to 47%
⭐ Popular amenities Kitchen, Internet and Pool
🏊  Vacation rentals with a pool 2,329 rentals
🌙 Minimum price starting at $18
🐾 Pet friendly vacation homes 2,247 rentals
🏡 Rentals available 9,406 rentals

Chicago: other vacation ideas

Other Popular Vacation Destinations

Destinations worth visiting near Chicago

Interesting destinations to consider for your next trip

image-tag