Chicago holiday rentals

Chicago holiday rentals

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Chicago, IL, United States
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Good to know

Low season

AprilCheapest month to stay with an average 35% drop in price.

High season

JulyMost expensive time to stay with an average 50% rise in price.

Average price (Weeknight)

€195Average Sunday to Thursday price over the last 2 weeks.

Average price (Weekend night)

€185Average Friday and Saturday 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 the perfect Chicago holiday rental

  • Kitchen/kitchenette, pet friendly, and hot tub are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 25% 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 Chicago Guest House on Lakewood Avenue (10.0, 36 reviews), Chicago Guest House On Newport Avenue (10.0, 26), and 2bd/2ba Near Wrigley, Lincoln Square. Family Friendly Boutique Hotel (9.9, 20), based on ratings and reviews from real travellers.
  • West Ridge is the neighbourhood in Chicago with the most affordable holiday rental properties (9 properties with an average price of €108 per night). Apartment for 6 to 8, Brand new apartment for 6 people and Retro-Chic Urban Oasis are the most popular rental properties in West Ridge.
  • 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.

FAQs when booking a holiday rental in Chicago

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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.