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Highwood, IL Homes for Rent

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  • /45

    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 $1,789 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
  • /20

    Starting at $5,600 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
  • /8

    Starting at $2,500 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
  • /23

    $1,980

    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
  • /30

    $1,900

    Total Monthly Price

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

    30 Michigan Ave Unit 2, Highwood, IL 60040

    30 Michigan ave is a two flat house in which the second floor is available for rent. Utilities are $150 additional to rent price. This 2 bedroom 1 bath is 800 square ft with a personal deck that is 300 square ft. This space has been completely renovated with brand new wood floors, new appliances, new cabinets, new bathroom and brand new patio ready for furniture. Parking spot available in

    30 Michigan Ave Unit 2, Highwood, IL 60040
  • /12

    $2,995

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 2,200 Sq Ft
    • House for Rent

    111 Pleasant Ave, Highwood, IL 60040

    Another single-family bespoke renovation by Green Dog Homes! Walk to Highwood’s trendy restaurants, coffee shops, and festivals and live your best life!Sunlit renovated chef’s kitchen with quartz countertops, all new appliances, and great storage. Dining room with views of professionally landscaped yard and family room with cozy wood-burning fireplace and built-in bookshelves complete the

    111 Pleasant Ave, Highwood, IL 60040
  • /28

    $4,072 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
  • /42

    $2,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Townhouse for Rent

    334 Euclid Ave, Highwood, IL 60040

    Welcome Home To This Beautifully Maintained 3-Bedroom, 2.5-Bath Half Duplex, Nestled On A Quiet Dead-End Street In A Prime Location. Filled With Natural Light, The Spacious Living & Dining Rooms Offer The Perfect Space For Everyday Living & Entertaining. The Generously Sized Kitchen Features A Cozy Breakfast Area, While All Three Bedrooms Provide Comfortable Living Space & Ample Closet Storage,

    Sandra Locascio RE/MAX Suburban

    334 Euclid Ave, 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
  • /20

    $3,300 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,204 Sq Ft
    • House for Rent

    111 Pleasant Ave, Highwood, IL 60040

    Charming single family home with beautiful hardwood floors, new windows and freshly painted throughout! Main level features living room with wood burning fireplace, built-ins and french doors. Separate dining room, and kitchen with all new appliances. Second floor has 3 nice sized bedrooms and a full bath. Lower level has half bath, laundry and plenty of space for storage. Outdoor spaces include

    Lane Klein Compass

    111 Pleasant Ave, 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 $2,947 per month, though prices vary by neighborhood, size, and property type. As of August 2026, condos tend to be the most affordable option while townhouses and single-family homes 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 $117,880 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 $2,947 per month in Highwood, IL, renters typically need to show $8,841 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 14.1, 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 West Highland Park, East Highland Park and Northeast Buffalo Grove, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
12
Median Rent
$2,947
Median Single Family Home Rent
$2,995
Median Townhouse Rent
$2,900
Median Condo Rent
$2,579
How to Rent a Home