Chicago vacation rentals

Chicago vacation rentals

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

Chicago, IL
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Good to know

Low season

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

High season

MarchMost expensive time to stay with an average 92% rise in price.

Average price (Weeknight)

$231Average Sunday to Thursday price over the last 2 weeks.

Average price (Weekend night)

$221Average Friday and Saturday price over the last 2 weeks.

When to book a vacation 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 vacation rental

  • Pool, air-conditioned, and kitchen/kitchenette are the most popular vacation rental property amenities in Chicago
  • Vacation rentals in Chicago are around 32% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chicago.
  • The best vacation rental properties in Chicago are Luxury Home Away From Your Home (9.6, 20 reviews), The Avondale Guesthouse (9.4, 45), and Wrigley Oasis! Steps from the Field! - 3BD 1BA (9.4, 45), based on ratings and reviews from real travelers.
  • West Ridge is the neighborhood in Chicago with the most affordable vacation rental properties (4 properties with an average price of $127 per night). Spacious 3BR Condo Perfect for Staycation, Vintage Condo With Whirlpool Tub, Fireplace And Open Floor Plan. Mins. To Lak, and Tastefully Designed 3BR Apt Bright and Stylish plus WiFi are the most popular rental properties in West Ridge.

FAQs when booking a vacation 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 vacation rental.