Chicago holiday rentals

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

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Chicago vacation rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

€0 - €197€197 - €394€394 - €590€590 - €787€787+ per night

Property type

ApartmentCondoHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Chicago

Show all
Sonder by Marriott Bonvoy The Burnham Apartments Loop - Chicago - Living room
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Near West Side
8.2Very Good(190)
Free Wi-Fi
Air conditioning
€300+
Check availability
Sonder by Marriott Bonvoy The Opal Apartments River North - Chicago - Balcony
Sonder by Marriott Bonvoy The Opal Apartments River North
Near North Side
8.7Very Good(196)
Free Wi-Fi
Air conditioning
€260+
Check availability
Beautiful Big 3 bedroom Quiet Apt near downtown - Chicago - Living room
Beautiful Big 3 bedroom Quiet Apt near downtown
South Side
9.4Wonderful(12)
Parking
Free Wi-Fi
Air conditioning
€237+
Check availability
Just Minutes from Downtown Chicago - Chicago - Bedroom
Just Minutes from Downtown Chicago
South Side
9.2Wonderful(4)
Parking
Free Wi-Fi
Air conditioning
€230+
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
9.1Wonderful(129)
Free Wi-Fi
Pet friendly
Air conditioning
€416+
Check availability
Cozy Garden studio Apartment - Chicago - Bedroom
Cozy Garden studio Apartment
South Side
€61+
Check availability
5430 Happy Home - Chicago
5430 Happy Home
South Side
8.1Very Good(281)
Parking
Free Wi-Fi
Air conditioning
€49+
Check availability
Simplified Living Space - Chicago
Simplified Living Space
South Side
4.5Mediocre(64)
Parking
Free Wi-Fi
Air conditioning
€69+
Check availability
Ginosi Chicago Apartel - Chicago
Ginosi Chicago Apartel
Near North Side
€454+
Check availability
Wrigleyville Suites - Chicago
Wrigleyville Suites
Wrigleyville
6.5Okay(19)
Parking
Free Wi-Fi
Air conditioning
€610+
Check availability
Kenwood Apartments, Downtown Hyde Park - Chicago
Kenwood Apartments, Downtown Hyde Park
South Side
6.4Okay(30)
Parking
Free Wi-Fi
Air conditioning
€153+
Check availability
Drexel Apartments, Downtown Hyde Park - Chicago
Drexel Apartments, Downtown Hyde Park
South Side
7.1Good(33)
Parking
Free Wi-Fi
Air conditioning
€107+
Check availability
Global Luxury Suites at the Chicago Loop - Chicago
Global Luxury Suites at the Chicago Loop
Downtown
8.9Very Good(30)
Free Wi-Fi
Air conditioning
€140+
Check availability
Entire Modern 2 Bedroom Apartment - Chicago
Entire Modern 2 Bedroom Apartment
Belmont Cragin
7.1Good(11)
Free Wi-Fi
Air conditioning
€247+
Check availability
Cozy 1 Bedroom Close To Downtown Chicago - Chicago
Cozy 1 Bedroom Close To Downtown Chicago
West Town
8.4Very Good(51)
Parking
Free Wi-Fi
Air conditioning
€229+
Check availability
Close to Downtown - Free Parking - Chicago
Close to Downtown - Free Parking
South Side
10Wonderful(1)
Parking
Free Wi-Fi
Air conditioning
€40+
Check 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.

Which month has the cheapest vacation rental rates in Chicago?

Vacation rentals are cheapest in Chicago in February, with average rates of €110. In comparison, November is the most expensive month, with prices at €1,385.

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 €164. The highest prices are found on Friday, with average rates at €333.

How early should you book a vacation rental in Chicago?

Book at least 55 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
July
€49
Cheapest month to stay with an average 31% drop in price.
Most expensive month to stay with an average 29% 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, airport shuttle, hot tub, pet friendly, and beachfront are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 54% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best holiday rental properties in Chicago are Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena (9.1, 129 reviews), Global Luxury Suites at the Chicago Loop (8.9, 30), and Sonder by Marriott Bonvoy The Opal Apartments River North (8.7, 196), based on ratings and reviews from real travellers.
  • Garfield Ridge is the neighbourhood in Chicago with the most affordable holiday rental properties (5 properties with an average price of €196 per night). Condo Apartment Near Midway Airport, Sunshiny Spacious 3 Bedroom 2 Bathroom Condo With Attached Rooftop Patio and Cozy and Comfy entire apartment for you! are the most popular rental properties in Garfield Ridge.
  • 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 May.
  • The cheapest night for renting a holiday home in Chicago is Wednesday. In contrast, the most expensive is Sunday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Chicago for 27 days.

FAQs when booking a holiday home in Chicago

  • 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 apartments, cabins, campgrounds, caravan parks, chalets, condos, cottages, houses, homestays, lodges 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 12% 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 €124. Search here for similar prices

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

    Holiday rentals in Near North Side, Lake View and Near West Side 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.

What Chicago holiday rental guests are talking about

Show all

Popular topics

Holiday rentals by topic

Show all
The Chicago Hotel Collection Millennium Park - Chicago
The Chicago Hotel Collection Millennium Park
Downtown
6.8Okay(2448)
Parking
€147+
Check availability
Wrigley Oasis! Steps from the Field! - 3BD 1BA - Chicago
Wrigley Oasis! Steps from the Field! - 3BD 1BA
Lake View
9.6Wonderful(87)
Parking
€434+
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
€216+
Check availability
Uptown Gem - Chicago
Uptown Gem
Uptown
9.9Wonderful(30)
Parking
€441+
Check availability
5430 Happy Home - Chicago
5430 Happy Home
South Side
8.1Very Good(281)
Parking
€49+
Check availability
Perfect place to enjoy the city or just relax - Chicago
Perfect place to enjoy the city or just relax
North Lawndale
8.6Very Good(132)
Parking
€190+
Check availability
Forrestville Ave Large Suite - Chicago
Forrestville Ave Large Suite
South Side
9.1Wonderful(142)
Parking
€142+
Check availability

Everything you need to know for your stay in Chicago

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

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.