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Chicago holiday rentals

Fri 19-7
Sat 20-7

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Best Chicago vacation rentals

Most recommended vacation rentals in Chicago

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The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit - Chicago
Free Wi-Fi
Your 1BR Homey Haven in Vibrant Chicago - Chicago
Your 1BR Homey Haven in Vibrant Chicago
10 Wonderful
North CenterS$ 343+
S$ 343+
5430 Happy Home
8.4 Very Good
South SideS$ 104+
S$ 104+
Free Wi-Fi
Simplified Living Space
5.8 Fair
EnglewoodS$ 108+
S$ 108+
Free Wi-Fi
Chicago City Stay
5.4 Fair
West TownS$ 201+
S$ 201+
Free Wi-Fi
Forrestville Ave Large Suite
9.2 Wonderful
South SideS$ 261+
S$ 261+
Free Wi-Fi

Good to know

Low season


High season


Average price (weeknight)

S$ 106

Average price (weekend night)

S$ 261
Cheapest month to stay with an average 70% drop in price.
Most expensive month to stay with an average 75% 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 holiday 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.
  • Pet-friendly, fitness, and beachfront are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 47% cheaper than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best holiday rental properties in Chicago are Wrigley Oasis! Steps from the Field! - 3BD 1BA (9.7, 62 reviews), Logan Square 2 Br/1 Ba-Modern, Near Metra (9.7, 20), and The Avondale Guesthouse (9.3, 130), based on ratings and reviews from real travellers.
  • Edgewater is the neighbourhood in Chicago with the most affordable holiday rental properties (28 properties with an average price of S$ 305 per night). Chic 2BR Suite w Gym & Meeting Room by Stay Gia, Minimalist Studio Apt in Edgewater and Modern 3BR Suite by Loyola University by Stay Gia are the most popular rental properties in Edgewater.
  • 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 October and May.
  • The cheapest night for renting a holiday home in Chicago is Saturday. In contrast, the most expensive is Sunday.
  • Book your Chicago holiday rental at least 34 days before your stay begins to get the best price.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Chicago for 1 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 S$ 2,699.

  • 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 S$ 11,568.

  • 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 and houses.

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

    There are a number of dog and pet-friendly Chicago holiday rentals, with around 13% allowing you to bring your pet along with you.

  • How much is a holiday rental in Chicago?

    KAYAK users have found holiday rentals in Chicago for as cheap as S$ 210 in the last 3 days. The average price is S$ 386.

  • 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 S$ 137. 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

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What Chicago holiday rental guests are talking about

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Landmarks in Chicago