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Highwood, IL Homes for Rent

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  • /50

    Starting at $2,532 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 $1,779 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
  • /11

    $2,800

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    250 High St Unit 1, Highwood, IL 60040

    250 High St Unit 1, Highwood, IL 60040
  • /28

    $3,824 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
  • /2

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Townhouse for Rent

    322 Euclid Ave, Highwood, IL 60040

    Beautifully remodeled 3 bedroom 2 bath duplex is fabulous Highwood location. Lovely updated kitchen, gorgeous hardwood floors throughout much of the home. Parking includes one garage space and one exterior space in the driveway. Close to all the amazing Highwood businesses, train, festivals and schools. Dogs and cats considered at owners discretion. No other pets considered. More photos coming

    Mada Hitchmough Compass

    322 Euclid Ave, Highwood, IL 60040
  • /17

    $2,500 Per Month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Apartment for Rent

    217 Highwood Ave Unit 1A, Highwood, IL 60040

    Highwood on the North Shore Apartment. This rental property offers approximately 900 square feet of living space with two bedrooms and one bathroom. The open concept layout connects the living room, dining room, and kitchen, creating a seamless flow throughout the residence. The kitchen is equipped with essential appliances and ample counter space for meal preparation. The bedrooms feature ample

    Carol Santi Coldwell Banker Realty

    217 Highwood Ave Unit 1A, Highwood, IL 60040
  • /13

    $2,800 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
  • /21

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • Condo for Rent

    2490 Green Bay Rd Unit 1, Highland Park, IL 60035

    Completely remodeled 3 bed/2 bath within walking distance to Schools, metra, shopping and more. Bright and spacious living room with wood burning fire place. Wood floors throughout. Updated kitchen with brand new refrigerator and plenty of storage. New W/D on main level. Dining area with access to side deck. Bedrooms share modern and brand new hallway bath. Back entry area provides access to

    Jacqueline Lotzof Compass

    2490 Green Bay Rd Unit 1, Highland Park, IL 60035

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 $2,800 per month, though prices vary by neighborhood, size, and property type. As of September 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 $112,000 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 $2,800 per month in Highwood, IL, renters typically need to show $8,400 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 19.1, 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 East Highland Park, Riverwoods Country Club Estates, Northeast Buffalo Grove and Southwest Waukegan, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
8
Median Rent
$2,800
Median Single Family Home Rent
$2,800
Median Townhouse Rent
$2,800
Median Condo Rent
$2,710
How to Rent a Home