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Chicago Public School District 299 Homes & Apartments For Rent

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      4849 W Gladys Ave, Chicago, IL 60644 - Photo 1
      Just Listed

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      4849 W Gladys Ave  #1  Chicago, IL 60644

      $1,800
      • Rental
      • Active
      • MLS # 12660702
      • Updated 12 hours ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,044
        Sq. Ft.

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      3161 N Cambridge Ave  #507  Chicago, IL 60657

      $1,750
      • Rental
      • Active
      • MLS # 12661311
      • Updated 5 days ago
      • 1
        Full Bath
      • 1
        Total Bath
      • 1
        Parking Space

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      933 W Sunnyside Ave  #1N  Chicago, IL 60640

      $1,750
      • Rental
      • Active
      • MLS # 12660904
      • Updated 5 days ago
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath
      • 550
        Sq. Ft.

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      7722 S Cornell Ave  #1W  Chicago, IL 60649

      $1,600
      • Condo
      • Active
      • MLS # 12662721
      • Updated 23 hours ago
      • 2
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 900
        Sq. Ft.

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      3621 S Winchester Ave  #2F  Chicago, IL 60609

      $1,600
      • Rental
      • Active
      • MLS # 12661429
      • Updated 4 days ago
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath
      • 700
        Sq. Ft.
      • 1
        Parking Space

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      6522 S Paulina St  #2  Chicago, IL 60636

      $1,600
      • Rental
      • Active
      • MLS # 12661449
      • Updated 4 days ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 900
        Sq. Ft.
      • 1
        Parking Space

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      4100 N Kedzie Ave  #2E  Chicago, IL 60618

      $1,600
      • Rental
      • Active
      • MLS # 12661185
      • Updated 5 days ago
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 550
        Sq. Ft.

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      6030 S Eberhart Ave  #B  Chicago, IL 60637

      $1,550
      • Condo
      • Active
      • MLS # 12661147
      • Updated 6 hours ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,500
        Sq. Ft.
      • 1
        Parking Space

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      6619 N Sheridan Rd, Chicago, IL 60626 - Photo 1 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 2 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 3 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 4 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 5 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 6 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 7 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 8 6619 N Sheridan Rd, Chicago, IL 60626 - Photo 9
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      6619 N Sheridan Rd  #305  Chicago, IL 60626

      $1,550
      • Rental
      • Active
      • MLS # 12655152
      • Updated 19 hours ago
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath
      • 850
        Sq. Ft.

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      4753 N Monticello Ave  #3A  Chicago, IL 60625

      $1,500
      • Rental
      • Active
      • MLS # 12661513
      • Updated 4 days ago
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath
      • 650
        Sq. Ft.

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      3933 N Clarendon Ave  #508  Chicago, IL 60613

      $1,500
      • Condo
      • Active
      • MLS # 12661124
      • Updated 5 days ago
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath

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      5849 S Francisco Ave  #1D  Chicago, IL 60629

      $1,395
      • Rental
      • Active
      • MLS # 12661617
      • Updated 4 days ago
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,200
        Sq. Ft.
      • 1
        Parking Space

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      8917 S Cottage Grove Ave  #2E  Chicago, IL 60619

      $1,350
      • Rental
      • Active
      • MLS # 12661438
      • Updated 6 hours ago
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 950
        Sq. Ft.

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      8046 S Pulaski Rd  #2  Chicago, IL 60652

      $1,350
      • Rental
      • Active
      • MLS # 12661393
      • Updated 4 days ago
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,000
        Sq. Ft.

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      2053 N Bingham St, Chicago, IL 60647 - Photo 1
      Sale Pending

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      2053 N Bingham St  #2  Chicago, IL 60647

      $2,150
      • Rental
      • Pending
      • MLS # 12659741
      • Updated 6 days ago
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 700
        Sq. Ft.
      • 1
        Parking Space
      Listed by Brian Somera (630) 408-1304 and Lucas Lyons (317) 507-0378

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      3238 N Southport Ave, Chicago, IL 60657 - Photo 1 3238 N Southport Ave, Chicago, IL 60657 - Photo 2 3238 N Southport Ave, Chicago, IL 60657 - Photo 3 3238 N Southport Ave, Chicago, IL 60657 - Photo 4 3238 N Southport Ave, Chicago, IL 60657 - Photo 5 3238 N Southport Ave, Chicago, IL 60657 - Photo 6 3238 N Southport Ave, Chicago, IL 60657 - Photo 7 3238 N Southport Ave, Chicago, IL 60657 - Photo 8 3238 N Southport Ave, Chicago, IL 60657 - Photo 9 3238 N Southport Ave, Chicago, IL 60657 - Photo 10 3238 N Southport Ave, Chicago, IL 60657 - Photo 11 3238 N Southport Ave, Chicago, IL 60657 - Photo 12 3238 N Southport Ave, Chicago, IL 60657 - Photo 13
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      3238 N Southport Ave  #1  Chicago, IL 60657

      $1,950
      • Rental
      • Active
      • MLS # 12657310
      • Updated 13 hours ago
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath
      Listed by Kristin Gonnella (773) 619-0215 and Phillip Weaver (773) 269-8471

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      5452 N Central Ave, Chicago, IL 60630 - Photo 1 5452 N Central Ave, Chicago, IL 60630 - Photo 2 5452 N Central Ave, Chicago, IL 60630 - Photo 3 5452 N Central Ave, Chicago, IL 60630 - Photo 4 5452 N Central Ave, Chicago, IL 60630 - Photo 5 5452 N Central Ave, Chicago, IL 60630 - Photo 6 5452 N Central Ave, Chicago, IL 60630 - Photo 7 5452 N Central Ave, Chicago, IL 60630 - Photo 8 5452 N Central Ave, Chicago, IL 60630 - Photo 9 5452 N Central Ave, Chicago, IL 60630 - Photo 10 5452 N Central Ave, Chicago, IL 60630 - Photo 11 5452 N Central Ave, Chicago, IL 60630 - Photo 12 5452 N Central Ave, Chicago, IL 60630 - Photo 13 5452 N Central Ave, Chicago, IL 60630 - Photo 14
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      5452 N Central Ave  #1  Chicago, IL 60630

      $1,850
      • Rental
      • Active
      • MLS # 12659187
      • Updated 13 hours ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,050
        Sq. Ft.
      Listed by Jacek Piktel (773) 655-7597

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      363 E Wacker Dr, Chicago, IL 60601 - Photo 1 363 E Wacker Dr, Chicago, IL 60601 - Photo 2 363 E Wacker Dr, Chicago, IL 60601 - Photo 3 363 E Wacker Dr, Chicago, IL 60601 - Photo 4 363 E Wacker Dr, Chicago, IL 60601 - Photo 5 363 E Wacker Dr, Chicago, IL 60601 - Photo 6 363 E Wacker Dr, Chicago, IL 60601 - Photo 7 363 E Wacker Dr, Chicago, IL 60601 - Photo 8 363 E Wacker Dr, Chicago, IL 60601 - Photo 9 363 E Wacker Dr, Chicago, IL 60601 - Photo 10 363 E Wacker Dr, Chicago, IL 60601 - Photo 11 363 E Wacker Dr, Chicago, IL 60601 - Photo 12 363 E Wacker Dr, Chicago, IL 60601 - Photo 13 363 E Wacker Dr, Chicago, IL 60601 - Photo 14 363 E Wacker Dr, Chicago, IL 60601 - Photo 15 363 E Wacker Dr, Chicago, IL 60601 - Photo 16 363 E Wacker Dr, Chicago, IL 60601 - Photo 17 363 E Wacker Dr, Chicago, IL 60601 - Photo 18 363 E Wacker Dr, Chicago, IL 60601 - Photo 19 363 E Wacker Dr, Chicago, IL 60601 - Photo 20 363 E Wacker Dr, Chicago, IL 60601 - Photo 21 363 E Wacker Dr, Chicago, IL 60601 - Photo 22 363 E Wacker Dr, Chicago, IL 60601 - Photo 23 363 E Wacker Dr, Chicago, IL 60601 - Photo 24 363 E Wacker Dr, Chicago, IL 60601 - Photo 25 363 E Wacker Dr, Chicago, IL 60601 - Photo 26 363 E Wacker Dr, Chicago, IL 60601 - Photo 27 363 E Wacker Dr, Chicago, IL 60601 - Photo 28 363 E Wacker Dr, Chicago, IL 60601 - Photo 29 363 E Wacker Dr, Chicago, IL 60601 - Photo 30 363 E Wacker Dr, Chicago, IL 60601 - Photo 31 363 E Wacker Dr, Chicago, IL 60601 - Photo 32 363 E Wacker Dr, Chicago, IL 60601 - Photo 33 363 E Wacker Dr, Chicago, IL 60601 - Photo 34 363 E Wacker Dr, Chicago, IL 60601 - Photo 35
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      363 E Wacker Dr  #3709  Chicago, IL 60601

      $14,000
      • Condo
      • Active
      • MLS # 12659122
      • Updated 6 hours ago
      • 3
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,763
        Sq. Ft.
      • 1
        Parking Space

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      2020 N Cleveland Ave, Chicago, IL 60614 - Photo 1 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 2 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 3 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 4 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 5 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 6 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 7 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 8 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 9 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 10 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 11 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 12 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 13 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 14 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 15 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 16 2020 N Cleveland Ave, Chicago, IL 60614 - Photo 17
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      2020 N Cleveland Ave  #A  Chicago, IL 60614

      $8,000
      • Townhouse
      • Active
      • MLS # 12651160
      • Updated 13 hours ago
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 2,600
        Sq. Ft.
      • 1
        Parking Space

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      no-photo Just Listed

      1400 N State Pkwy  #5DEF  Chicago, IL 60610

      $6,500
      • Rental
      • Active
      • MLS # 12660160
      • Updated 6 hours ago
      • 3
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 3,000
        Sq. Ft.
      • 2
        Parking Spaces

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      719 N Elizabeth St, Chicago, IL 60642 - Photo 1 719 N Elizabeth St, Chicago, IL 60642 - Photo 2 719 N Elizabeth St, Chicago, IL 60642 - Photo 3 719 N Elizabeth St, Chicago, IL 60642 - Photo 4 719 N Elizabeth St, Chicago, IL 60642 - Photo 5 719 N Elizabeth St, Chicago, IL 60642 - Photo 6 719 N Elizabeth St, Chicago, IL 60642 - Photo 7 719 N Elizabeth St, Chicago, IL 60642 - Photo 8 719 N Elizabeth St, Chicago, IL 60642 - Photo 9 719 N Elizabeth St, Chicago, IL 60642 - Photo 10 719 N Elizabeth St, Chicago, IL 60642 - Photo 11 719 N Elizabeth St, Chicago, IL 60642 - Photo 12 719 N Elizabeth St, Chicago, IL 60642 - Photo 13 719 N Elizabeth St, Chicago, IL 60642 - Photo 14 719 N Elizabeth St, Chicago, IL 60642 - Photo 15 719 N Elizabeth St, Chicago, IL 60642 - Photo 16 719 N Elizabeth St, Chicago, IL 60642 - Photo 17 719 N Elizabeth St, Chicago, IL 60642 - Photo 18 719 N Elizabeth St, Chicago, IL 60642 - Photo 19 719 N Elizabeth St, Chicago, IL 60642 - Photo 20 719 N Elizabeth St, Chicago, IL 60642 - Photo 21 719 N Elizabeth St, Chicago, IL 60642 - Photo 22 719 N Elizabeth St, Chicago, IL 60642 - Photo 23 719 N Elizabeth St, Chicago, IL 60642 - Photo 24 719 N Elizabeth St, Chicago, IL 60642 - Photo 25 719 N Elizabeth St, Chicago, IL 60642 - Photo 26 719 N Elizabeth St, Chicago, IL 60642 - Photo 27
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      719 N Elizabeth St  #3S  Chicago, IL 60642

      $6,500
      • Condo
      • Active
      • MLS # 12659163
      • Updated 13 hours ago
      • 3
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 2,400
        Sq. Ft.
      • 1
        Parking Space

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      1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 1 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 2 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 3 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 4 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 5 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 6 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 7 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 8 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 9 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 10 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 11 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 12 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 13 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 14 1440 N Milwaukee Ave, Chicago, IL 60622 - Photo 15
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      1440 N Milwaukee Ave  #4  Chicago, IL 60622

      $5,000
      • Condo
      • Active
      • MLS # 12659761
      • Updated 13 hours ago
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 1,800
        Sq. Ft.

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      no-photo Just Listed

      33 W Huron St  #305  Chicago, IL 60654

      $4,500
      • Condo
      • Active
      • MLS # 12655062
      • Updated 13 hours ago
      • 2
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,461
        Sq. Ft.
      • 1
        Parking Space

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      1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 1 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 2 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 3 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 4 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 5 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 6 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 7 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 8 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 9 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 10 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 11 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 12 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 13 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 14 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 15 1001 N Milwaukee Ave, Chicago, IL 60642 - Photo 16
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      1001 N Milwaukee Ave  #204  Chicago, IL 60642

      $4,500
      • Condo
      • Active
      • MLS # 12659104
      • Updated 13 hours ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,634
        Sq. Ft.
      • 2
        Parking Spaces

      Save this searchYou’ll get email updates when new properties matching this criteria go on the market. You can also run these searches quickly under “Properties & Searches” at the top of every page. and receive alerts when new properties are listed.

      Find Apartments and Homes for Rent in the Chicago Public School District 299, Chicago, IL

      Coldwell Banker Realty can help you find Chicago Public School District 299 apartments and rentals. Refine your Chicago Public School District 299 rental search results by price, property type, bedrooms, baths and other features. Need more information? View our Chicago real estate offices and let us help you find the perfect rental or apartment.

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      Based on information submitted to the MRED as of Jun 2 2026 3:37PM. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. MRED DMCA Notice

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