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Chicago vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in Chicago

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Best Chicago vacation rentals

Most recommended vacation rentals in Chicago

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Cabin 101 by 747 Lofts - Chicago - Building
Cabin 101 by 747 Lofts
West Town
8.8Very good(28)
Free Wi-Fi
$213+
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Wrigleyville Suites - Chicago - Living room
Wrigleyville Suites
Wrigleyville
6.2Okay(14)
Parking
Free Wi-Fi
$998+
Check availability
Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena - Chicago - Bedroom
Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena
Near South Side
8.9Very good(122)
Free Wi-Fi
Pet friendly
$346+
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Just Minutes from Downtown Chicago - Chicago - Bedroom
Just Minutes from Downtown Chicago
South Side
9.2Wonderful(4)
Parking
Free Wi-Fi
$267+
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The Avondale Attic - Chicago - Bedroom
The Avondale Attic
Irving Park
9.8Wonderful(7)
Parking
Free Wi-Fi
$218+
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Cozy Garden studio Apartment - Chicago - Bedroom
Cozy Garden studio Apartment
South Side
$71+
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Roscoe Village Guesthouse - Chicago - Dining room
Roscoe Village Guesthouse
Chicago, IL
8.0Very good(4)
Free Wi-Fi
$228+
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5430 Happy Home - Chicago
5430 Happy Home
South Side
8.2Very good(260)
Parking
Free Wi-Fi
$89+
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Simplified Living Space - Chicago
Simplified Living Space
South Side
4.8Mediocre(61)
Parking
Free Wi-Fi
$79+
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Ginosi Chicago Apartel - Chicago
Ginosi Chicago Apartel
Near North Side
$527+
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Global Luxury Suites at the Chicago Loop - Chicago
Global Luxury Suites at the Chicago Loop
Downtown
8.9Very good(30)
Free Wi-Fi
$162+
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Chicago Downtown River North - Chicago
Chicago Downtown River North
Near North Side
6.8Okay(16)
Free Wi-Fi
$132+
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Red Robin Rentals - Avenue on Kenwood - Chicago
Red Robin Rentals - Avenue on Kenwood
South Side
7.2Good(18)
Parking
Free Wi-Fi
$184+
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Entire Modern 2 Bedroom Apartment - Chicago
Entire Modern 2 Bedroom Apartment
Belmont Cragin
8.7Very good(9)
Free Wi-Fi
$299+
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Cozy 1 Bedroom Close To Downtown Chicago - Chicago
Cozy 1 Bedroom Close To Downtown Chicago
West Town
8.6Very good(45)
Parking
Free Wi-Fi
$287+
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Navy Pier Suite Id 31 - Chicago
Navy Pier Suite Id 31
Near North Side
$355+
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KAYAK’s insights for vacation rentals in Chicago

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chicago with confidence.

Which month has the cheapest vacation rental rates in Chicago?

Vacation rentals are cheapest in Chicago in February, with average rates of $154. In comparison, September is the most expensive month, with prices at $1,138.

What is the cheapest day of the week to book a vacation rental in Chicago?

Monday offers the lowest rates in Chicago, with an average nightly price of $193. The highest prices are found on Thursday, with average rates at $341.

How early should you book a vacation rental in Chicago?

Book at least 66 days before your stay begins to get the best price for your Chicago vacation rental.
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Good to know

Low season

February

High season

September

Average price (weeknight)

$243

Average price (weekend night)

$271
Cheapest month to stay with an average 39% drop in price.
Most expensive month to stay with an average 351% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chicago vacation rental deals

  • Are you traveling to Chicago on business? Consider staying at the Wicker Park Chicago in the historical Wicker Park area. This establishment is only six blocks from both Damien and Division Blueline bus stops. It saves you from the inconvenience of getting around the city thanks to its proximity to public transportation. This vacation rental is close to great restaurants and bars where guests can dine, including Smoke Daddy BBQ – Wicker Park, Innertown Pub, Milk and Honey Café, and Seadog Sushi Bar.
  • For those looking to visit famous attractions in Chicago, consider staying at Level Chicago Old Town. This Chicago vacation rental is within minutes of several attractions such as the Chicago History Museum, Architech Gallery, and Second City Theatre.
  • If you are a pet owner looking for a pet-friendly Chicago house rental, consider staying at Beautiful Room in Chicago. This vacation rental allows furry friends on request, but charges may apply. Any damages caused by the pet are charged to your account. However, it is only minutes away from Douglas Park, where you can walk and play with your pet.
  • For those traveling to Chicago for a family vacation, consider staying at Homan Square. This family-friendly vacation rental has a family room, among other family-friendly amenities, where you and your loved ones can relax and enjoy some screen time after a hyperactive day at Garfield Park, only a short distance away. This Chicago vacation rental also offers complimentary snacks and drinks to families using the family room.
  • Golf enthusiasts looking to enjoy a round of golf during their visit to Chicago will enjoy a stay at Forrestville Ave Large Suite. Within two miles of the vacation rental is a well-maintained golf course fully equipped with golf equipment, including golf carts, clubs, and balls. Guests are also provided with complimentary drinks, which should be relaxing, especially after a whole day of golf.
  • Pet friendly, pool, air-conditioned, parking, airport shuttle, hot tub, and beachfront are the most popular vacation rental property amenities in Chicago
  • Vacation rentals in Chicago are around 18% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best vacation rental properties in Chicago are Sonder South Wabash | Superior One-Bedroom Apartment (9.4, 23 reviews), Aurelien Spacious Apartments in the Heart of Gold Coast (9.2, 20), and The Bright Retreat in Andersonville (9.2, 25), based on ratings and reviews from real travelers.
  • Kenwood is the neighborhood in Chicago with the most affordable vacation rental properties (32 properties with an average price of $229 per night). Drexel Apartments, Downtown Hyde Park, Hyde Park Modern Private Room - Near Univ of Chicago, and Modern Coach House 2BR/1BA/Den in Hyde Park/ Kenwood, walk to U of C & Lakefront are the most popular rental properties in Kenwood.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chicago for 6 days.
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FAQs when booking a vacation home in Chicago

  • How much is a vacation rental for a week in Chicago?

    The average price for a weekly Chicago vacation rental found by KAYAK users in the last 2 weeks is $1,599.

  • How much is a vacation rental for a month in Chicago?

    The average price for a monthly Chicago vacation rental found by KAYAK users in the last 2 weeks is $6,851.

  • What types of vacation rentals are available in Chicago?

    There are loads of different property types that you can make your vacation home in Chicago. You’ll find apartments, cabins, campgrounds, caravan parks, chalets, condos, cottages, houses, homestays, lodges and villas.

  • What are some of the most-loved vacation rentals available in Chicago?

    There are many types of properties available for Chicago vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Forrestville Ave Large Suite and Entire Modern 2 Bedroom Apartment.

  • What are the most popular Chicago vacation rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated vacation homes that can sleep 6 people or more by KAYAK users are Forrestville Ave Large Suite and Entire Modern 2 Bedroom Apartment.

  • Are there any pet-friendly vacation rentals in Chicago?

    There are a number of dog and pet-friendly Chicago vacation rentals, with around 15% allowing you to bring your pet along with you.

  • How much is a vacation rental in Chicago for tonight?

    In the last 72 hours, users have found Chicago vacation rentals for tonight for as low as $136. Search here for similar prices

  • What are the most popular Chicago neighborhoods to book a vacation rental in?

    Vacation rentals in Near North Side, Downtown and Loop have the most searches on KAYAK. For more information about Chicago's different neighborhoods, check out our Chicago's City Guide.

  • How can I find vacation rentals near me in Chicago?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Which Chicago vacation rental offers fitness facilities?

    If you enjoy physical fitness and are looking for a vacation rental with a fitness center, consider staying at Ginosi Chicago Apartel. This Chicago vacation rental comes with a well-equipped fitness center with treadmills and exercise bikes, among others. The gym also provides guests with a personal trainer to assist both beginners and pros.

  • Which Chicago vacation rental has a pool?

    For those who enjoy swimming, consider staying at Uptown Gem. This establishment has a great indoor heated pool where you can relax and unwind as you sip on delicious cocktails by the pool. Wicker lounge chairs are also available for guests who would like to sit and relax by the pool. The management also stations a lifeguard at the pool to ensure the safety of swimmers.

  • Which vacation rental in Chicago offers laundry services?

    If you’re visiting Chicago and are looking for a vacation rental that provides laundry services, consider staying at Entire 2br. This Chicago house rental provides laundry services convenient for travelers with families or on business. The vacation rental also ensures that the guest’s laundry is well handled, and you shouldn’t worry about any misplacement while they’re being laundered.

  • What are the benefits of self-catering in the Chicago vacation rentals?

    Choose a vacation rental when you want to be more indipendent and you want to come and go as you please. When you are staying in a vacation rental you can cook your own meals and experience Chicago as a true local!

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Where to stay in Chicago?

Our map will help you find the perfect place to stay in Chicago by showing you the exact location of each vacation rental.

What Chicago vacation rental guests are talking about

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Vacation rentals by topic

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Wrigley Oasis! Steps from the Field! - 3BD 1BA - Chicago
Wrigley Oasis! Steps from the Field! - 3BD 1BA
Lake View
9.6Wonderful(86)
Parking
$458+
Check availability
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy! - Chicago
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
Uptown
9.4Wonderful(28)
Parking
$250+
Check availability
Uptown Gem - Chicago
Uptown Gem
Uptown
9.9Wonderful(30)
Parking
$501+
Check availability
5430 Happy Home - Chicago
5430 Happy Home
South Side
8.2Very good(260)
Parking
$89+
Check availability
Perfect place to enjoy the city or just relax - Chicago
Perfect place to enjoy the city or just relax
North Lawndale
8.8Very good(124)
Parking
$218+
Check availability
Forrestville Ave Large Suite - Chicago
Forrestville Ave Large Suite
South Side
9.0Wonderful(135)
Parking
$186+
Check availability

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Everything you need to know for your stay in Chicago

Chicago vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Chicago. Find cheap vacation homes to rent in Chicago. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Chicago that suits you best.

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