14

Highwood, IL Homes for Rent under $2,500

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  • /48

    Starting at $2,248 Per Month

    • 1 - 3 Beds

    440 Green Bay Rd, Highwood, IL 60040

    Welcome to Highpoint Highwood Station 440 — modern 1, 2 & 3-bedroom apartments for rent in Highwood, IL. Enjoy updated kitchens, in-unit laundry, and walkable access to downtown Highwood, Green Bay Road, and Fort Sheridan. Our pet-friendly community offers convenient living near Highland Park, boutique dining, and local shops. Schedule your tour today.

    HIGHPOINT Highwood Station 440

    440 Green Bay Rd, Highwood, IL 60040
  • /35

    Starting at $1,759 Per Month

    • 1 - 3 Beds

    634 Sheridan Rd, Highwood, IL 60040

    Nestled between affluent Lake Forest and Highland Park, Arrive North Shore® is located in vibrant downtown Highwood and offers a unique opportunity to live on Chicago's scenic North Shore, just minutes away from Downtown Highwood shops and restaurants and Fort Sheridan Metra Stations. Our newly restyled apartment homes are equipped with deluxe kitchens, generous living spaces, and private patios.

    Arrive North Shore

    634 Sheridan Rd, Highwood, IL 60040
  • /8

    Starting at $2,300 Per Month

    • 2 Beds

    318 Walker Ave, Highland Park, IL 60035

    Welcome to this beautifully situated apartment home nestled on a quiet, tree-lined street in one of Highland Park's most desirable neighborhoods. This spacious property offers a bright, comfortable layout with generous living areas, abundant natural light, and timeless character throughout.The location can't be beat just minutes from downtown Highland Park, 1/2 mile to Metra & Lake

    318 Walker Ave, Highland Park, IL 60035
  • /19

    $2,100

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    350 Prairie Ave Unit A, Highwood, IL 60040

    Spacious and charming 3-bedroom apartment available in Highwood, IL, located in a brick duplex (upstairs unit in a 2-unit building). Just a short stroll to downtown Highwood and the Highwood Train Station, with easy access to Highway 41 right around the corner. This unit features a generous kitchen and dining area, along with a large living room ideal for relaxation. The apartment includes one

    350 Prairie Ave Unit A, Highwood, IL 60040
  • /23

    $2,000

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    113 Burtis Ave Unit A, Highwood, IL 60040

    **PLEASE READ CAREFULLY & THOROUGHLY**We are renting a perfect 2-bedroom 1-bath apartment in a wonderfully quiet neighborhood in Highwood. Just renovated in May 2026. It's also within walking distance to Highwood's bustling business district and train station. Located right off Half Day Rd/Rte 22, making it very close to Highway 41.This first-floor apartment is composed of a large

    113 Burtis Ave Unit A, Highwood, IL 60040

Rental Home Trends

Number of Homes for Rent
5
Median Rent
$2,995
Median Single Family Home Rent
$2,973
Median Townhouse Rent
$4,125
Median Condo Rent
$2,700
How to Rent a Home