Chicago vacation rentals

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Best Chicago vacation rentals

Most recommended vacation rentals in Chicago

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Modern 2BR Flats - Right Next to Wrigley Field & Transit - Cubs! - Chicago - Living room
Free Wi-Fi
Pet friendly
The Avondale Guesthouse - Chicago - Living room
The Avondale Guesthouse
9.4 Wonderful
AvondaleC$ 262+
C$ 262+
Free Wi-Fi
Pet friendly
Entire Modern 2 Bedroom Apartment
8.6 Very good
Belmont CraginC$ 288+
C$ 288+
Free Wi-Fi
5430 Happy Home
8.4 Very good
South SideC$ 94+
C$ 94+
Free Wi-Fi
Simplified Living Space
6 Okay
EnglewoodC$ 91+
C$ 91+
Free Wi-Fi

Good to know

Low season


High season


Average price (weeknight)

C$ 231

Average price (weekend night)

C$ 295
Cheapest month to stay with an average 50% drop in price.
Most expensive month to stay with an average 196% rise in price.
Average Sun. - Thu. price over the last 2 weeks.
Average Fri. & Sat. price over the last 2 weeks.

When to book a vacation rental in Chicago

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

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.
  • Hot tub, pool, and kitchen/kitchenette are the most popular vacation rental property amenities in Chicago
  • Vacation rentals in Chicago are around 50% 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 Wrigley Oasis! Steps from the Field! - 3BD 1BA (9.7, 44 reviews), 2F Chicago's Little Italy near West Loop & Downtown (9.6, 60), and The Avondale Guesthouse (9.4, 120), based on ratings and reviews from real travelers.
  • Lake View is the neighborhood in Chicago with the most affordable vacation rental properties (212 properties with an average price of C$ 185 per night). Modern 2BR Flats - Right Next to Wrigley Field & Transit - Cubs!, Sophisticated Studio Apartment with Modern Kitchen - Oakdale OD2 rep, and Relaxing 1BR Apt in Lakeview near Best Restaurants - Belmont H6 are the most popular rental properties in Lake View.
  • If you’re looking for a cheap vacation rental in Chicago, you should consider visiting during the low season. The cheapest vacation homes in Chicago can be found in June and February.
  • The cheapest night for renting a vacation home in Chicago is Monday. In contrast, the most expensive is Saturday.
  • Book your Chicago vacation rental at least 16 days before your stay begins to get the best price.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chicago for 1 days.
  • The cheapest Chicago vacation rental found on KAYAK in the last 2 weeks was C$ 114, while the most expensive was C$ 187.

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 C$ 3,901.

  • 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 C$ 16,717.

  • 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, houses, homestays and condos.

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

    There are a number of dog and pet-friendly Chicago vacation rentals, with around 17% allowing you to bring your pet along with you.

  • How much is a vacation rental in Chicago?

    KAYAK users have found vacation rentals in Chicago for as cheap as C$ 143 in the last 3 days. The average price is C$ 557.

  • 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 C$ 202. Search here for similar prices

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

    Vacation rentals in Near North Side, Lake View and Near West Side 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!

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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What Chicago vacation rental guests are talking about

Vacation rentals by topic

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Wrigley Oasis! Steps from the Field! - 3BD 1BA - Chicago
C$ 531+
Uptown Gem - Chicago
Uptown Gem
8.8 Very good
UptownC$ 280+
C$ 280+
5430 Happy Home
8.4 Very good
South SideC$ 94+
C$ 94+
Forrestville Ave Large Suite
9.3 Wonderful
South SideC$ 166+
C$ 166+

Popular topics

Landmarks in Chicago