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Short Term Rentals in Chicago, IL

Short Term Rentals in Chicago, IL. 391 Rentals Available
391 Rentals Available
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  • Rent specials
    Ask for pricing
    Verified Listing

    4.5 (2)
    707 N. Wells St., Chicago, IL 60654
    Apply online • Pet friendly • Parking
  • a living room with a couch and a table and a tv
    7 units available
    Studio $1,013+
    1 bd $1,400
    Base rent
    Verified Listing

    3.5 (4)
    5330 S Blackstone Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • A living room with a grey sofa, a wooden coffee table, and a painting on the wall.
    Rent specials 205 units available
    Studio $1,040+
    1 bd $1,205
    2 bd $1,525+
    Base rent
    Verified Listing

    3233 S King Drive, Chicago, IL 60616
    Apply online • Pet friendly
  • A living room with a grey couch and a wooden coffee table.
    1 bd $1,675
    2 bd $1,950
    Base rent
    Verified Listing

    4.0 (1)
    2025 N. Damen Ave., Chicago, IL 60647
    Apply online • Pet friendly
  • a kitchen with a sink and a stove and a window
    Only 3 units left
    1 bd $1,720
    Base rent
    Verified Listing

    5439-45 S Woodlawn Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • a living room with chairs and a black and white picture
    Rent specials
    Ask for pricing
    Verified Listing

    4.5 (2)
    707 N. Wells St., Chicago, IL 60654
    Apply online • Pet friendly • Parking
  • a kitchen with dark wood cabinets and a stainless steel refrigerator
    7 units available
    Studio $1,195+
    1 bd $1,550
    Base rent
    Verified Listing

    5316 S Dorchester Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • a living room with a mirror and a wood floor
    Rent specials Only 1 unit left
    Studio $1,419+
    Base rent
    Verified Listing

    3.5 (12)
    660 - 678 N. Dearborn St., Chicago, IL 60654
    Apply online • Cat friendly
  • an empty kitchen with black cabinets and a stove and sink
    New units available Only 2 units left
    Studio $1,295+
    Base rent
    Verified Listing

    3.0 (3)
    1429 W Lunt Ave, Chicago, IL 60626
    Apply online • Pet friendly
  • a living room with a couch and a television
    Studio $1,545+
    1 bd $1,705+
    2 bd $2,595+
    Base rent
    Verified Listing

    4.5 (40)
    14 West Elm Street, Chicago, IL 60610
    Apply online • Cat friendly
  • a kitchen with stainless steel appliances and wooden floors
    Only 2 units left
    2 bd $1,750
    Base rent
    Verified Listing

    7434 N Artesian Ave, Chicago, IL 60645
    Apply online • Pet friendly
  • a kitchen with stainless steel appliances and a window
    Only 3 units left
    Studio $1,400
    2 bd $1,825
    Base rent
    Verified Listing

    4.5 (2)
    7539 N Bell Ave, Chicago, IL 60645
    Apply online • Pet friendly
  • a living room with a couch and a rug
    Rent specials
    Studio $1,550
    Base rent
    Verified Listing

    4.0 (11)
    911 W. Oakdale Ave., Chicago, IL 60657
    Apply online • Pet friendly
  • an empty living room with wood floors and a window
    7 units available
    Studio $1,007+
    1 bd $1,736
    Base rent
    Verified Listing

    3.0 (2)
    5455 S Blackstone Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • A living room with a large couch and a view of the ocean.
    Rent specials New units available
    Studio $2,546+
    1 bd $2,839+
    2 bd $4,384+
    Base rent
    Verified Listing

    4.0 (7)
    1210 S Indiana Ave, Chicago, IL 60605
    Apply online • Pet friendly
  • A living room with a grey sofa, a coffee table, and a television playing a golf game.
    Only 1 unit left
    2 bd $1,620
    Base rent
    Verified Listing

    5.0 (2)
    2340 N California Ave, Chicago, IL 60647
    Apply online • Pet friendly
  • a parking garage filled with lots of cars
    New units available 16 units available
    Studio $1,197+
    1 bd $1,282+
    2 bd $1,811+
    Base rent
    Verified Listing

    4.0 (69)
    6700 S. Oglesby Ave., Chicago, IL 60649
    Apply online • Pet friendly
  • a kitchen with a table and a refrigerator
    4 units available
    Studio $1,352+
    Base rent
    Verified Listing

    4.0 (19)
    420 W. Fullerton Pkwy., Chicago, IL 60614
    Apply online • Pet friendly
  • A living room with a white couch and a painting on the wall.
    Only 1 unit left
    1 bd $1,630
    Base rent
    Verified Listing

    4.5 (5)
    5525 N Winthrop, Chicago, IL 60640
    Apply online • Pet friendly
  • a living room with couches and a coffee table
    9 units available
    Studio $1,134+
    1 bd $1,573+
    Base rent
    Verified Listing

    3.5 (7)
    5514 S Blackstone Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • A living room with a fireplace and a television on the wall.
    Rent specials
    2 bd $1,965
    Base rent
    Verified Listing

    4.0 (11)
    2500-08 W. Pensacola Ave., Chicago, IL 60618
    Apply online • Pet friendly
  • a living room with a couch and a table and a ceiling fan
    New units available 15 units available
    Studio $1,087+
    1 bd $1,468+
    Base rent
    Verified Listing

    4.0 (66)
    5541 S. Everett Ave., Chicago, IL 60637
    Apply online • Pet friendly
  • A kitchen with a table and chairs in the middle of the room.
    Rent specials
    2 bd $2,895+
    3 bd $3,100
    Base rent
    Verified Listing

    4410 N Clark St, Chicago, IL 60640
    Apply online • Pet friendly
  • a kitchen with stainless steel appliances and wooden cabinets
    4 units available
    1 bd $1,515
    2 bd $1,650
    Base rent
    Verified Listing

    3.0 (6)
    1433-45 W. Lunt Ave., Chicago, IL 60626
    Apply online • Pet friendly
  • a white kitchen with stainless steel appliances and white cabinets
    Only 1 unit left
    4 bd $3,595
    Base rent
    Verified Listing

    4.0 (1)
    1209 E Madison Park, Chicago, IL 60615
    Apply online • Cat friendly
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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 $1,040 and $13,700.

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

There are 322 short-term rentals available on RentCafe. Prices and availability in Chicago, IL were last updated on 2 Jun 2026.

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

The average Chicago, IL short-term rental size is 443 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.