Photo by Tara Jabbari

Search Apartments in Highwood

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 310 Apartments in Highwood with updated reviews, rates, and availability.

Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (50)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (14)
"Great time and location. "
The price is AED 364
AED 959 total
includes taxes & fees
19 May - 20 May
2-bedroom apartment just 2 minutes drive to Wrigley Field
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (19)
"This place was perfect for us, and right where we needed it to be. "
Charming Wrigleyville Home Close to the Cubs!
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
Fridge, microwave, oven, stovetop

Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94

10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay at Toby's place. The property is as listed, very accommodating, everything we needed was provided! The host was very responsive within minutes of contacting. The place was very clean and well kept! The bed is very comfortable however if sleeping with a partner you will feel their every move. Parking can be difficult if you stay out late! If you can't find a spot on belle plaine try whipple. Would definitely stay here again. "
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Terrace/patio

Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!

9.4 out of 10, Exceptional, (20)
"Really nice space for an extended stay. Clean and thoughtfully decorated. Has all of the amenities you need."
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Property grounds

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover

8.8 out of 10, Excellent, (9)
"This lovely apartment was a great location for our family. Close to shops and restaurants. Easy walk to the Red Line train. The place was well stocked with bedding and the mattresses were quite comfy. We enjoyed cooking and hanging out in the living area. "
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (22)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is AED 316
AED 901 total
includes taxes & fees
19 May - 20 May
Bright Garden Studio
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Pool

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (98)
"We had a great stay here in December. Communication was great and the property owner was very nice and helpful! Would definitely recommend this location. We will definitely return on our next trip if it’s available. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Fridge, microwave, oven, stovetop

Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square

3.0 star property
10.0 out of 10, Exceptional, (13)
"Everything was as advertised. "
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Beach

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

10.0 out of 10, Exceptional, (222)
"Great rental, lovely, easy in and out."
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Great Location-Beautiful Friendly Andersonville Neighborhood
Smart TV, books

Great Location-Beautiful Friendly Andersonville Neighborhood

10.0 out of 10, Exceptional, (181)
"Beautiful building! Comfy beds, well-stocked pantry with essentials. Great location, 2 blocks from CLark Street, but really quiet. Paul was great with communication."
Great Location-Beautiful Friendly Andersonville Neighborhood
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Terrace/patio

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (28)
"This place is convenient for a short stay. near the L Train and shops and restaurants. "
The price is AED 202
AED 743 total
includes taxes & fees
20 May - 21 May
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Cozy W Front Porch DT Libertyville near Naval Base
Miscellaneous

Cozy W Front Porch DT Libertyville near Naval Base

9.4 out of 10, Exceptional, (11)
"Older house but it suited our needs perfectly. Host was very responsive when we couldn’t get access on check in. "
Cozy W Front Porch DT Libertyville near Naval Base
"Hope of Evanston" 180°view, 2BDR +2Bath Urban luxury
Interior

"Hope of Evanston" 180°view, 2BDR +2Bath Urban luxury

10.0 out of 10, Exceptional, (17)
"We really enjoyed our time here. The condo was great and management very responsive to questions. "
"Hope of Evanston" 180°view, 2BDR +2Bath Urban luxury
Elegant 3 Bedroom and 1 Bath Apartment
3 bedrooms, desk, iron/ironing board, free WiFi

Elegant 3 Bedroom and 1 Bath Apartment

9.0 out of 10, Wonderful, (10)
"Very nice place - can easily fit quite a few people! Host was very accommodating, place was clean and comfortable. My friends and I had a great time! "
Elegant 3 Bedroom and 1 Bath Apartment
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Exterior

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (177)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Smart TV

Cozy 2BR/1BA Garden Apartment Near Lincoln Square

8.0 out of 10, Very Good, (9)
"very good for the peice"
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Luxury 5Bed 2Bath Apt w/Parking
Fridge, microwave, oven, stovetop

Luxury 5Bed 2Bath Apt w/Parking

Luxury 5Bed 2Bath Apt w/Parking
Chic studio in Loyola University with WiFi, fitness room, steps from the lake
Fridge, oven, stovetop, coffee/tea maker

Chic studio in Loyola University with WiFi, fitness room, steps from the lake

9.0 out of 10, Wonderful, (4)
"It's a new place with comfortable but bare bones furniture. A few more tables or dressers wouldn't hurt. The area is great with lots of restaurant options. Street parking was generally easy. Nice place."
Chic studio in Loyola University with WiFi, fitness room, steps from the lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Highwood
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Highwood

The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (61)
"This hotel was outstanding in all respects. "
The price is AED 737
AED 844 total
includes taxes & fees
3 Jun - 4 Jun
The Gem Museum Suites
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (22)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is AED 316
AED 901 total
includes taxes & fees
19 May - 20 May
Bright Garden Studio
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (14)
"Great time and location. "
The price is AED 364
AED 959 total
includes taxes & fees
19 May - 20 May
2-bedroom apartment just 2 minutes drive to Wrigley Field
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's it like to stay at an apartment in Highwood?
There are plenty of places to stay with in the Chicago area, with 5061 accommodation choices including 2561 apartments. Visit some favorite places in the larger area like Naval Base Great Lakes and Six Flags Great America.
How do you know if an apartment is a good option for your stay?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, and also for families wanting the conveniences of home.
What's a favorite apartment I should consider for a stay in Highwood?
Below are some of the more popular apartments in the area: 2-bedroom apartment just 2 minutes drive to Wrigley Field: Located in Chicago, 18.7 mi/30.2 km from the heart of Highwood. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Bright Garden Studio: Located 13.6 mi/21.8 km away in Evanston. Private patios, fireplaces, and separate dining areas are included. Access to onsite laundry facilities is available on site. Charming Wrigleyville Home Close to the Cubs!: Located in Chicago, 19.2 mi/31 km away. Includes Smart TVs. Access to onsite laundry facilities is available on site.
What will the weather be like when I travel to Highwood?
Weather is only one factor, but it can really affect your travel plans, especially when you’re planning an extended stay in Highwood. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Highwood is 47 inches.
What are the must-see places to visit in Highwood?
While exploring the area, visit family-friendly sights like Six Flags Great America, or get outside and enjoy nature at Chicago Botanic Garden. In the larger area, you’ll find Naval Base Great Lakes and Lake Forest College.
What's the best way to get to and around Highwood?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Chicago, IL (PWK-Chicago Executive), which is located 7.6 mi (12.3 km) away from the heart of the city. You can also search for flights into Chicago O’Hare Intl. Airport (ORD), which is 16.6 mi (26.6 km) away. To venture out into the surrounding area, ride one of the trains from Highwood Station or Highland Park Fort Sheridan Station.