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

FebruaryCheapest month to stay with an average 71% drop in price.

High season

DecemberMost expensive time to stay with an average 99% rise in price.

Average price (Weeknight)

£87Average Sunday to Thursday price over the last 2 weeks.

Average price (Weekend night)

£230Average 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

  • Pool, kitchen/kitchenette, and pet friendly are the most popular holiday rental property amenities in Chicago
  • Holiday rentals in Chicago are around 56% 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 2bd/2ba Near Wrigley, Lincoln Square. Family Friendly Boutique Hotel (9.9, 20 reviews), 52nd Floor Magmile Penthouse - Views, Fireplace, Fitness Center, Pool, Wifi (9.7, 20), and Wrigley Oasis! Steps from the Field! - 3BD 1BA (9.5, 48), based on ratings and reviews from real travellers.
  • Grand Boulevard is the neighbourhood in Chicago with the most affordable holiday rental properties (22 properties with an average price of £124 per night). Forrestville Ave Large Suite, Skydeck Experience at Indiana Place and McCormick Place Experience at Indiana Place are the most popular rental properties in Grand Boulevard.

FAQs when booking a holiday rental in Chicago

How much is a holiday rental in Chicago?

How much is a holiday rental in Chicago for tonight?

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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.