Vacation Rentals in Chicago

Vacation Rentals in Chicago

Start comparing over 1,219 rentals in Chicago and book at the best price!

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Highlights Chicago

  • World class galleries and museums
  • Sporting spectacles
  • Beautiful skyline
  • Lakefront setting
  • Good public transportation
  • Shopping

Best Vacation Rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 5 Guests in Chicago, Cook County
Vacation Rental for 5 Guests in Chicago, Cook County, Picture 1
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Chicago, Cook County
Vacation Rental • 1130 ft² • 2 Bedrooms
It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.The Space:SLEEPING ARRANGEMENT:- Bedroom 1: 1 king-size bed (sleeps 2)- Bedroom 2: 2 twin-size beds (s...
from $257 / night
Vacation Rental for 3 Guests in Chicago, Cook County
Vacation Rental for 3 Guests in Chicago, Cook County, Picture 1
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Chicago, Cook County
Vacation Rental • 743 ft² • 1 Bedroom
With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connected to the Chicago scene you're seeking. Other nearby attractions include Millennium Park, the Chicago Children’s Museum, and the Lincoln Park Zoo. Check-in is quick and easy; each person in your group 18 and older will need to present a photo ID upon check-in with the building concierge. We'll send check-in instructions via email before you arrive. We look forward to hosting you!The Space:SLEEPING ARRANGEMENT:- Bedroom 1: 1 king-size bed (sleeps 2)- Living room: sleeper sofa (sleeps...
from $182 / night
Vacation Rental for 2 Guests in Chicago, Cook County
Vacation Rental for 2 Guests in Chicago, Cook County, Picture 1
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Chicago, Cook County
Vacation Rental • 635 ft² • 2 Guests
With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connected to the Chicago scene you're seeking. Other nearby attractions include Millennium Park, the Chicago Children’s Museum, and the Lincoln Park Zoo. Check-in is quick and easy; each person in your group 18 and older will need to present a photo ID upon check-in with the building concierge. We'll send check-in instructions via email before you arrive. We look forward to hosting you!The Space:SLEEPING ARRANGEMENT:- Living Area: 1 queen-size bed (sleeps 2)PARKING:- On-site parking availa...
from $153 / night

Other holiday ideas and property types in Chicago that might be interesting

Popular Destinations in Chicago

    Prices and availability

    Current Vacation rental prices in Chicago

    $477for 22 Jun - 29 Jun
    $435 annual average
    Jul
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    Average price per week

    Current vacation rental availability in Chicago

    4%for 22 Jun - 29 Jun
    30% annual average
    Jul
    Aug
    Sep
    Oct
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    Percentage of available rentals

    Chicago Vacation Rentals

    Elegant City Center Vacation Homes

    America’s third largest city, Chicago is full of wonderful vacation rental options. For example, if you look inside the Loop, you’ll find plenty of upscale apartment properties, with multiple bathrooms, bedrooms and huge living areas – all within walking distance of the subway and major attractions.

    Choose a Lakefront Vacation Home or a Suburban Villa

    You don’t need to stay in the center of Chicago. One of the great things about the city is the beautiful shorefront of Lake Michigan. Check out lakefront neighborhoods like Lincoln Park, the Near North Side or Gold Coast. Or look inland to roomy vacation rental options in affluent suburbs like Wheaton or Itasca. There’s no shortage of fantastic accommodation possibilities in the Windy City.

    Vacationing in Chicago

    A Lakefront Metropolis with Incredible Energy

    Chicago is clustered around the southern curve of Lake Michigan in the state of Illinois, roughly a quarter of the distance from New York to California. The gateway to the Midwest, Chicago is easy to reach thanks to O’Hare International Airport, which connects the city to every state in the US, and international destinations as well.

    Find the Loop, and You’ve Found Chicago’s Downtown Center

    In the city itself, the lake is an easy reference point. Chicago’s city center is nestled up against the lake, inside what locals call “the Loop” – which referred to the route of the elevated railway. Nowadays, the L Train network runs into the Loop from north, south, and the west, and it’s the focal point for most tourist visits.

    Hundreds of Neighborhoods to Explore

    However, Chicago is a massive city, with over 10 million people in the metro area. Within that area, there are plenty of sights and areas to explore, from Frank Lloyd Wright houses in Hyde Park to BrookfieldZoo. It’s all fairly spread out, so renting a car and choosing a rental home with parking space makes perfect sense.

    Downtown Chicago
    Downtown Chicago

    Activities

    A World Class Cultural Destination

    Chicago has an endless array of cultural attractions. There’s a huge Blues Festival in June, the delights of the Art Institute of Chicago, the huge Field Museum and the Museum of Science. If you love art, science or music, you can’t go wrong in Chicago.

    Sporting Attractions All Year-Round

    Chicago is also a major sporting destination. From the NFL’s Bears to the Bulls of the NBA and Major League Baseball’s Cubs, sports fans will have an excuse to visit the city at almost any time of year.

    A Superb Place if You Love to Shop

    The home of Sears is a major shopping hub for the Midwest. For those who need some retail therapy, the Magnificent Mile on Michigan Avenue hosts one of the highest concentrations of boutiques in the USA, while State Street is home to huge department stores like Marshall Field's.

    The famous Route 66 highway begins right outside the doors of the Art Institute of Chicago

    Top 5 things to do in Chicago

    1. Visit the city’s huge number of museums

    Chicago’s museum collection is incredible. The Field Museum is a massive natural history center, the Art Institute hosts a huge collection of modern art, the Chicago History Museum teaches visitors about the city’s fascinating past, while the Science Museum immerses guests in the world of technology.

    2. Ascend to the panoramic deck of the John Hancock Center

    There’s no better place to witness the breathtaking skyline of Chicago than the observation deck of the soaring John Hancock Tower, which is accessible by a high-speed elevator (which is an attraction in itself). Be sure to take your camera.

    3. Explore the Chicago Riverwalk

    The south bank of the Chicago River has been turned into one of America’s finest urban walkways, with attractions like tiki bars, birdwatching tours, water taxis, wine bars and brewery pubs dotted along its route.

    4. Try a Chicago deep dish pizza

    Deep dish pizza is one of Chicago’s culinary specialties. If you want to try a slice, head to local institutions like Pequod’s, the Art of Pizza or Giordano’s for a pizza pie that you will never forget.

    5. Head to Soldier Field, Wrigley Field or the United Center for sporting action

    Chicago’s teams are all in the top bracket of their sports, so whether you love NFL, NBA, Major League Baseball or even soccer or hockey, be sure to catch a contest during your stay.

    The Chicago Loop
    The Chicago Loop

    Useful Information

    Climate

    Chicago’s climate is something to think about if you are planning a visit. Because of its location at the center of the continent, Chicago experiences extremely cold winters (and the legendary wind), and hot summers. Visit in fall or late spring for the best sightseeing conditions. However, summer is festival season in Chicago, so if you are keen to attend open air music concerts, you’ll want to visit between June and September.

    Getting Around

    Getting around the city is fairly easy. You can travel from most suburban vacation rental home options via CTA buses or trains. If you do rely on public transportation, be sure to investigate day and week passes, as they are a great way to save money. You can also purchase City Passes to reduce the cost of visiting the major attractions.

    FAQs: Vacation Rentals in Chicago

    On average, what was the cost for vacation rentals in Chicago last year?

    Last year, rentals in this destination had an annual average price of around $369 per night.

    During which months can you find the best price for vacation rentals in Chicago?

    If you would like to save as much as possible during your visit to Chicago, pack your bags and travel there in February ($307 per night on average), April ($312), or March ($313), to find the lowest prices for the whole year.

    When does the price of vacation rentals in Chicago go up the most?

    When it comes to looking for a vacation rental in Chicago, the most expensive months are, in order of highest to lowest, September, August and October, with average prices per night of $432, $413, and $409, respectively.

    Should I plan a trip to Chicago well in advance?

    If you decide to put Chicago on your bucket list, we suggest planning your visit long before you go because it is usually very high in demand, with an annual average of 82% of rentals booked the previous year.

    Which months offer the highest availability?

    February, May and January are, in order of highest to lowest, the months offering the largest number of accommodations available, with an average availability of 27%, 26%, and 24%. However, even during these months, when the availability is the highest, the average is just 25%. So we highly recommend you always book your vacation early in Chicago.

    When are fewer rentals available in Chicago?

    During this period, the availability is only 9%. It is therefore preferable to book early.

    Are there many rentals in Chicago?

    In Chicago we offer you an extensive catalog of around 720 properties, with options to suit everyone, thanks to our 6 local and international providers.

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