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Short Term Rentals in Chicago, IL

Short Term Rentals in Chicago, IL. 225 Rentals Available
225 Rentals Available
Quick filters
  • an empty kitchen with wooden cabinets and stainless steel appliances
    Ask for pricing
    Verified Listing

    5073 N Wolcott Ave, Chicago, IL 60640
    Pet friendly
  • a living room with a couch and a television
    Studio $1,300+
    Base rent
    Verified Listing

    14 West Elm Street, Chicago, IL 60610
    Apply online • Cat friendly
  • a living room with a couch and a round table
    Ask for pricing
    Income restricted
    Verified Listing

    2101 S. Michigan Ave, Chicago, IL 60616
    Pet friendly
53-0-city

Frequently asked questions

What is the price of a short-term rental in Chicago, IL?

The price range for a short-term rental in Chicago, IL is between $1,025 and $22,000.

How many short-term rentals are available in Chicago, IL on RentCafe?

There are 174 short-term rentals available on RentCafe. Prices and availability in Chicago, IL were last updated on 26 May 2026.

What is the average size of a short-term rental in Chicago, IL?

The average Chicago, IL short-term rental size is 382 sq. ft..

What are the advantages of renting a short-term rental in Chicago, IL?

Short-term rentals offer flexibility and are ideal for temporary stays or transitional periods.

What are the downsides of renting a short-term rental in Chicago, IL?

Short-term rentals typically cost more per month and may have limited availability.