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Highwood, IL Homes for Rent

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  • /49

    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
  • /20

    Starting at $5,500 Per Month

    • 3 Beds

    425 Bloom St, Highland Park, IL 60035

    Discover luxury living at 425 Bloom St Townhomes, a beautiful community of spacious 3 bedroom, 2.5 bathroom townhomes totaling 2,000 sqft. Each home offers a bonus office/flex space, perfect for remote work or extra living area. Enjoy the convenience of a private entrance and an attached 2-car garage. Nestled within a charming courtyard setting, this pet-friendly community is located in the

    Bloom Street Townhomes

    425 Bloom St, 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
  • /13

    $2,035 Per Month

    • 1 Bed
    • 1 Bath
    • 699 Sq Ft
    • Apartment for Rent

    546 Green Bay Rd Unit 408, Highwood, IL 60040

    Luxury Living in the Heart of Highwood! This stunning 1-bedroom, 1-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully

    Christopher Dumitru Crosstown Realtors, Inc.

    546 Green Bay Rd Unit 408, Highwood, IL 60040
  • /13

    $2,700 Per Month

    • 1 Bed
    • 1 Bath
    • 814 Sq Ft
    • Apartment for Rent

    246 Green Bay Rd Unit 404, Highwood, IL 60040

    Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine

    Christopher Dumitru Crosstown Realtors, Inc.

    246 Green Bay Rd Unit 404, Highwood, IL 60040
  • /13

    $2,550 Per Month

    • 3 Beds
    • 1 Bath
    • Apartment for Rent

    522 N Central Ave Unit 1, Highwood, IL 60040

    Beautifully updated 2-flat featuring a spacious first-floor apartment with 3 bedrooms and 1 bath. The well-designed open floor plan offers abundant natural light, an updated kitchen and bath, custom closet organizers, and window treatments throughout. Enjoy the convenience of a large private bonus room with washer and dryer. The property also includes access to a wonderful yard and 1 garage

    Diana Martinez Realty of America, LLC

    522 N Central Ave Unit 1, Highwood, IL 60040
  • /13

    $2,350 Per Month

    • 1 Bed
    • 1 Bath
    • 742 Sq Ft
    • Apartment for Rent

    246 Green Bay Rd Unit 310, Highwood, IL 60040

    Luxurious apartments feature high-end kitchens with 42-inch cabinets, stone countertops, breakfast bars, over-the-stove microwaves, and dishwashers. They also offer nine-foot ceilings, outdoor spaces, spacious closets, and in-unit washer and dryers. This modern rental community is situated in the heart of Highwood's historic downtown entertainment center, providing easy access to shopping, fine

    Christopher Dumitru Crosstown Realtors, Inc.

    246 Green Bay Rd Unit 310, Highwood, IL 60040
  • /28

    $4,249 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft
    • Townhouse for Rent

    20 Webster Ave Unit C, Highwood, IL 60040

    Rarely available Highwood 3 bedroom, 2.5 bathroom townhome is now available. This listing boasts hardwood floors throughout each floor, central air conditioning and heat, and washer / dryer in the unit. Granite countertops and stainless steel appliances (incl. dishwasher) in massive kitchen. More than ample countertop and cabinet space to enjoy. Large & sunny living area with separate dining

    Daniel Management Group Daniel Management Group Inc

    20 Webster Ave Unit C, Highwood, IL 60040
  • /15

    $3,193 Per Month

    • 2 Beds
    • 2 Baths
    • 1,028 Sq Ft
    • Apartment for Rent

    546 Green Bay Rd Unit 507, Highwood, IL 60040

    Luxury Living in the Heart of Highwood! This stunning 2-bedroom, 2-bathroom apartment offers modern elegance with a private terrace and generous closet space. Nestled in Highwood's vibrant historic downtown, you're just steps from premier shopping, fine dining, and the Metra station for effortless commuting. The building features a selection of 1, 2, and 3-bedroom residences, each thoughtfully

    Christopher Dumitru Crosstown Realtors, Inc.

    546 Green Bay Rd Unit 507, Highwood, IL 60040
  • /13

    $2,995 Per Month

    • 3 Beds
    • 1 Bath
    • Apartment for Rent

    423 Funston Ave Unit 2F, Highwood, IL 60040

    Lovely rehabbed 3 bedroom apartment ideally located close to all the action in the vibrant village of Highwood. This inviting home features a modern kitchen with granite countertops, gas cooking, and ample storage. Both bedrooms are generously sized and offer flexibility for a variety of needs, while the bonus space is perfect for a dedicated home office.The beautifully updated bathroom features

    Axel Cohen Compass

    423 Funston Ave Unit 2F, Highwood, IL 60040
  • /13

    $2,409 Per Month

    • 1 Bed
    • 1 Bath
    • 862 Sq Ft
    • Apartment for Rent

    440 Green Bay Rd Unit 401, Highwood, IL 60040

    This one-bedroom apartment boasts high ceilings, a balcony, and spacious closets. It is situated in the vibrant heart of Highwood's historic downtown entertainment center, with easy access to shopping, fine dining, and a Metra station just steps away. The building offers a variety of one, two, and three-bedroom options, all featuring luxurious kitchens and bathrooms, balconies, central heating,

    Christopher Dumitru Crosstown Realtors, Inc.

    440 Green Bay Rd Unit 401, Highwood, IL 60040

Why Live in Highwood

Named for its status as the tallest point between Chicago and Milwaukee, Highwood is a North Shore suburb known for its established downtown district. “It’s a community, with bars, restaurants and entertainment,” says Mike Del Monte, a broker with ...

Frequently Asked Questions

How much does it cost to rent a home in Highwood, IL?
The median rent for a home in Highwood, IL is $2,479 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Highwood, IL?
To comfortably afford the median rent in Highwood, IL, a household needs to earn roughly $99,160 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,479 per month in Highwood, IL, renters typically need to show $7,437 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Highwood, IL?
In Highwood, IL, the price-to-rent ratio is 15.5, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Highwood, IL are best for renting a home?
The best neighborhood for renting in Highwood, IL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include West Highland Park, East Highland Park, Northeast Buffalo Grove and Southwest Waukegan, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
14
Median Rent
$2,479
Median Single Family Home Rent
$2,638
Median Townhouse Rent
$4,125
Median Condo Rent
$2,458
How to Rent a Home