Chicago holiday rentals

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Best Chicago vacation rentals

Most recommended vacation rentals in Chicago

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The Double Play, Wrigley Flats - Located Right next to Wrigley - Chicago - Living room
Free Wi-Fi
Pet friendly
Air conditioning
River West, Third Floor Chicago by 747 Lofts - Chicago - Building
€118+
Free Wi-Fi
Air conditioning
Just Minutes from Downtown Chicago
9.2 Wonderful
South Side€238+
€238+
Parking
Free Wi-Fi
Air conditioning
Wrigleyville Suites
7.1 Good
Wrigleyville€441+
€441+
Parking
Free Wi-Fi
Air conditioning
5430 Happy Home
8 Very Good
South Side€84+
€84+
Parking
Free Wi-Fi
Air conditioning
Simplified Living Space
5 Fair
South Side€75+
€75+
Parking
Free Wi-Fi
Air conditioning
Global Luxury Apartments in Chicago
8.9 Very Good
Downtown€156+
€156+
Free Wi-Fi
Air conditioning
Entire Modern 2 Bedroom Apartment
8.7 Very Good
Belmont Cragin€198+
€198+
Free Wi-Fi
Air conditioning
Navy Pier Suite Id 31
Near North Side€342+
€342+
Air conditioning
Cozy 1 Bedroom Close To Downtown Chicago
8.7 Very Good
West Town€204+
€204+
Parking
Free Wi-Fi
Air conditioning
Red Robin Rentals - Avenue on Kenwood
7.7 Good
South Side€110+
€110+
Parking
Free Wi-Fi
Air conditioning

Good to know

Low season

May

High season

October

Average price (weeknight)

€109

Average price (weekend night)

€246
Cheapest month to stay with an average 29% drop in price.
Most expensive month to stay with an average 20% 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, pool, air-conditioned, hot tub, airport shuttle, parking, and beachfront are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 44% 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 The Avondale Guesthouse (9.2, 161 reviews), Forrestville Ave Large Suite (9.0, 132), and Global Luxury Apartments in Chicago (8.9, 30), based on ratings and reviews from real travellers.
  • Garfield Ridge is the neighbourhood in Chicago with the most affordable holiday rental properties (4 properties with an average price of €99 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 May and July.
  • The cheapest night for renting a holiday home in Chicago is Wednesday. In contrast, the most expensive is Friday.
  • Book your Chicago holiday rental at least 7 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 26 days.
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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 €3,343.

  • 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 €14,325.

  • 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, homestays, houses and condos.

  • 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 €88. 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.

  • How much is a holiday rental in Chicago?

    KAYAK users have found holiday rentals in Chicago for as cheap as €98 in the last 3 days. The average price is €478.

  • 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 holiday rental.

What Chicago holiday rental guests are talking about

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Holiday rentals by topic

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Wrigley Oasis! Steps from the Field! - 3BD 1BA - Chicago
€295+
Parking
Uptown Gem
8.6 Very Good
Uptown€228+
€228+
Parking
5430 Happy Home
8 Very Good
South Side€84+
€84+
Parking

Popular topics

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.

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