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Short Term Rentals in Chicago, IL

Short Term Rentals in Chicago, IL. 439 Rentals Available
439 Rentals Available
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  • Rent specials Only 2 units left
    2 bd $3,799
    3 bd $5,221+
    Base rent
    Verified Listing

    4.5 (2)
    707 N. Wells St., Chicago, IL 60654
    Apply online • Pet friendly • Parking
  • 228 units available
    Studio $1,045+
    1 bd $1,215+
    2 bd $1,500+
    Base rent
    Verified Listing

    3233 S King Drive, Chicago, IL 60616
    Apply online • Pet friendly
  • Only 3 units left
    Studio $1,025+
    1 bd $1,356+
    2 bd $2,187+
    Base rent
    Verified Listing

    3.5 (28)
    5100 S. Cornell Ave., Chicago, IL 60615
    Apply online • Pet friendly
  • Only 1 unit left
    Studio $1,295
    Base rent
    Verified Listing

    3.0 (3)
    1429 W Lunt Ave, Chicago, IL 60626
    Apply online • Pet friendly
  • Only 3 units left
    2 bd $1,815+
    Base rent
    Verified Listing

    1414 W Devon Ave, Chicago, IL 60660
    Apply online • Pet friendly
  • Rent specials Only 2 units left
    2 bd $3,799
    3 bd $5,221+
    Base rent
    Verified Listing

    4.5 (2)
    707 N. Wells St., Chicago, IL 60654
    Apply online • Pet friendly • Parking
  • Studio $1,430+
    2 bd $2,595+
    Base rent
    Verified Listing

    4.5 (40)
    14 West Elm Street, Chicago, IL 60610
    Apply online • Cat friendly
  • Only 1 unit left
    2 bd $2,150
    Base rent
    Verified Listing

    4.5 (1)
    6922 N Greenview Ave, Chicago, IL 60626
    Apply online • Pet friendly
  • 5 units available
    Studio $1,230
    1 bd $1,460
    Base rent
    Verified Listing

    4.5 (1)
    5532 S Kenwood Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • 1 bd $1,675
    Base rent
    Verified Listing

    4.0 (1)
    2025 N. Damen Ave., Chicago, IL 60647
    Apply online • Pet friendly
  • Only 2 units left
    3 bd $2,395+
    Base rent
    Verified Listing

    4.0 (3)
    5430 S Drexel, Chicago, IL 60615
    Apply online • Cat friendly
  • 8 units available
    Studio $1,350
    1 bd $1,495+
    Base rent
    Verified Listing

    3.0 (5)
    6748 N Ashland Ave, Chicago, IL 60626
    Apply online • Pet friendly
  • Only 2 units left
    2 bd $1,710+
    Base rent
    Verified Listing

    7434 N Artesian Ave, Chicago, IL 60645
    Apply online • Pet friendly
  • 16 units available
    Studio $1,060+
    1 bd $1,448+
    Base rent
    Verified Listing

    4.0 (66)
    5541 S. Everett Ave., Chicago, IL 60637
    Apply online • Pet friendly
  • Only 2 units left
    1 bd $2,358+
    Base rent
    Verified Listing

    4.5 (1)
    1879 North Milwaukee, Chicago, IL 60647
    Apply online • Pet friendly
  • New units available 10 units available
    1 bd $1,274+
    2 bd $1,811+
    Base rent
    Verified Listing

    4.0 (69)
    6700 S. Oglesby Ave., Chicago, IL 60649
    Apply online • Pet friendly
  • New units available Only 3 units left
    1 bd $1,475
    2 bd $1,515
    Base rent
    Verified Listing

    4.0 (6)
    6500 N Claremont Ave, Chicago, IL 60645
    Apply online • Pet friendly
  • Rent specials Only 2 units left
    Studio $1,405+
    Base rent
    Verified Listing

    3.5 (12)
    660 - 678 N. Dearborn St., Chicago, IL 60654
    Apply online • Cat friendly
  • 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
  • Ask for pricing
    Verified Listing

    4.0 (5)
    2038 W Touhy Ave, Chicago, IL 60645
    Apply online • Pet friendly
  • 9 units available
    Studio $1,177+
    1 bd $1,580+
    2 bd $2,012
    Base rent
    Verified Listing

    3.5 (7)
    5514 S Blackstone Ave, Chicago, IL 60615
    Apply online • Pet friendly
  • Rent specials
    2 bd $2,925+
    Base rent
    Verified Listing

    4410 N Clark St, Chicago, IL 60640
    Apply online • Pet friendly
  • Rent specials
    1 bd $1,795+
    Base rent
    Verified Listing

    4.0 (11)
    2500-08 W. Pensacola Ave., Chicago, IL 60618
    Apply online • Pet friendly
  • Only 1 unit left
    Studio $1,375
    Base rent
    Verified Listing

    4.5 (5)
    5525 N Winthrop, Chicago, IL 60640
    Apply online • Pet friendly
  • Rent specials
    2 bd $2,250
    Base rent
    Verified Listing

    3.5 (6)
    2156 W. Grace St., Chicago, IL 60618
    Apply online • Pet 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 $1,005 and $13,700.

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

There are 360 short-term rentals available on RentCafe. Prices and availability in Chicago, IL were last updated on 14 May 2026.

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

The average Chicago, IL short-term rental size is 431 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.