Chicago holiday rentals

Chicago holiday rentals

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

Chicago, IL, United States
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Good to know

Low season

JanuaryCheapest month to stay with an average 60% drop in price.

High season

OctoberMost expensive time to stay with an average 25% rise in price.

Average price (Weeknight)

€216Average Sunday to Thursday price over the last 2 weeks.

Average price (Weekend night)

€208Average Friday and Saturday price over the last 2 weeks.

Top tips for finding the perfect Chicago holiday rental

  • Pool, kitchen/kitchenette, and pet friendly are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 6% 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 Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom (9.9, 20 reviews), Logan Square: Chic, Comfy 1st Floor 2 Bdrm Apt! Parking Incld! (9.8, 28), and Wrigley Oasis! Steps from the Field! - 3BD 1BA (9.5, 59), based on ratings and reviews from real travellers.
  • Hyde Park is the neighbourhood in Chicago with the most affordable holiday rental properties (34 properties with an average price of €105 per night). SEE Chicago from a safe, convenient, and affordable, location!, Steps to UChicago, Sci Museum & Lake with Gym by Zencity and Classic Hp 2br With Fast Transit To Uchicago & Dt By Zencity are the most popular rental properties in Hyde Park.

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.