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Chicago holiday rentals

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

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Booking Insights
Recommended by KAYAK

Best Chicago vacation rentals

These are the best prices for 17-18 Oct.
Mccormick Place Guest House - Chicago - Balcony
Mccormick Place Guest House
Douglas
5.4Fair(383)
Homestay
$293+
View availability
Bright and Cozy 1BR Apartment in Logan Square! - Chicago - Living room
Bright and Cozy 1BR Apartment in Logan Square!
Logan Square
9.9Wonderful(43)
Apartment
$264+
View availability
Beautifully Remodeled Third Floor Flat in River North - 3N - Chicago - Room amenity
Beautifully Remodeled Third Floor Flat in River North - 3N
Near North Side
8.1Very Good(31)
Apartment
$337+
View availability
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover - Chicago - Living room
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Edgewater
9.7Wonderful(36)
Condo
$778+
View availability
Chi-Town Chill - Get Anywhere in the City from This Perfectly Located Duplex by AllSet Turnover - Chicago - Kitchen
Chi-Town Chill - Get Anywhere in the City from This Perfectly Located Duplex by AllSet Turnover
North Lawndale
9.6Wonderful(6)
Apartment
$546+
View availability
Kasa Magnificent Mile Chicago - Chicago - Building
Kasa Magnificent Mile Chicago
Near North Side
10Wonderful(1)
Apartment
$265+
View availability
Beautiful Unit Chi In Prime River North - 1 - Chicago - Bedroom
Beautiful Unit Chi In Prime River North - 1
Near North Side
9.0Wonderful(29)
Apartment
$591+
View availability
Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover - Chicago - Living room
Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover
Lower West Side
10Wonderful(2)
Apartment
$469+
View availability
2 New Construction Suites Same Place - Chicago - Living room
2 New Construction Suites Same Place
Lincoln Park
9.2Wonderful(28)
Apartment
$829+
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Chic, Cozy home, by Blue Line Train Stop + Free parking - Chicago - Living room
Chic, Cozy home, by Blue Line Train Stop + Free parking
Irving Park
9.0Wonderful(93)
Apartment
$223+
View availability
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover - Chicago - Kitchen
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
North Center
9.2Wonderful(14)
Apartment
$611+
View availability
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover - Chicago - Living room
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover
North Center
9.2Wonderful(8)
Apartment
$698+
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Breathtaking & Bright: Designer 2BD with Garage - Chicago - Living room
Breathtaking & Bright: Designer 2BD with Garage
Near West Side
10Wonderful(2)
Apartment
$625+
View availability
Spacious Luxury Townhouse - Old Town by AllSet Turnover - Chicago - Living room
Spacious Luxury Townhouse - Old Town by AllSet Turnover
Lincoln Park
8.5Very Good(12)
House
$878+
View availability
Perfect place to enjoy the city or just relax - Chicago
Perfect place to enjoy the city or just relax
North Lawndale
8.3Very Good(161)
Apartment
$233+
View availability
Stylish Chicago Retreat: Walk to Loyola University - Chicago
Stylish Chicago Retreat: Walk to Loyola University
Edgewater
9.8Wonderful(21)
Apartment
$653+
View availability
Booking Insights

KAYAK’s insights for holiday rentals in Chicago

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

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

Sunday offers the lowest rates in Chicago, with an average nightly price of $360. The highest prices are found on Thursday, with average rates at $489.

How much is a vacation rental in Chicago for tonight by property type?

The best deal for a vacation rental in Chicago found by KAYAK users in the last 5 days was $414 in a Homestay. Apartment prices start at $1,175.

How much is a vacation rental in Chicago for this weekend by property type?

The best deal for a vacation rental in Chicago found by KAYAK users for the upcoming weekend was $138 in a Homestay. Apartments prices start at $425 and Condos at $1,046.

How early should you book a vacation rental in Chicago?

Book at least 50 days before your stay begins to get the best price for your Chicago vacation rental.

Find deals

Good to know

Low season

High season

Average price (weeknight)

August
September
$415
Cheapest month to stay with an average 28% drop in price.
Most expensive month to stay with an average 85% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Chicago holiday 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.
  • Pool, parking, air-conditioned, hot tub, and wifi are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 399% cheaper than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best holiday rental properties in Chicago are Bright and Cozy 1BR Apartment in Logan Square! (9.9, 43 reviews), Stylish Chicago Retreat: Walk to Loyola University (9.8, 21), and Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover (9.7, 36), based on ratings and reviews from real travellers.
  • Kenwood is the neighbourhood in Chicago with the most affordable holiday rental properties (16 properties with an average price of $408 per night). 2BR Apt in Hyde Park - Algonquin 8E, Lakeside Retreat: Charming Greystone Near Downtown and The Penthouse, Lux stay near Downtown, UofC & Lake are the most popular rental properties in Kenwood.
  • If you’re looking for a cheap holiday rental in Chicago, you should consider visiting during the low season. The cheapest holiday homes in Chicago can be found in August and September.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Chicago for 22 days.

FAQs when booking a holiday home in Chicago

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

    The average price for a weekly Chicago holiday rental found by KAYAK users in the last 2 weeks is $1,839.

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

    The average price for a monthly Chicago holiday rental found by KAYAK users in the last 2 weeks is $7,880.

  • What types of holiday rentals are available in Chicago?

    There are loads of different property types that you can make your holiday home in Chicago. You’ll find agritourism, apartments, bed & breakfasts, condos, cottages, houses, homestays, hotels and villas.

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

    There are a number of dog and pet-friendly Chicago holiday rentals, with around 16% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Chicago holiday rentals for tonight for as low as $414. Search here for similar prices

  • How much is a holiday rental in Chicago for this weekend?

    In the last 72 hours, users have found Chicago holiday rentals for this weekend for as low as $138 per night. Search here for similar prices

  • Which are the most popular neighbourhoods to stay in Chicago?

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

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

    Take a look at our holiday rentals map to find the best holiday 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!

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 holiday rental.

More options for your stay in Chicago