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Chicago vacation rentals

Chicago vacation rentals

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

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)

C$ 279Average Sunday to Thursday price over the last 2 weeks.

Average price (Weekend night)

C$ 264Average 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, pet friendly, and wifi are the most popular vacation rental property amenities in Chicago
  • Vacation 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 vacation rental properties in Chicago are River North's Rock N' Roll - In The Heart Of The City (9.7, 20 reviews), Luxury Home Away From Your Home (9.5, 20), and The Avondale Guesthouse (9.4, 49), 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 C$ 157 per night). Vintage Condo With Whirlpool Tub, Fireplace And Open Floor Plan. Mins. To Lak, Spacious 3BR Condo Perfect for Staycation, and Retro-Chic Urban Oasis 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.