Photo by Tara Jabbari

Search Apartments in Highwood

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Apartments in Highwood

Uptown Studio Gem Sum

The price is SAR 371
SAR 680 total
includes taxes & fees
7 Jul - 8 Jul
Uptown Studio Gem Sum

Montrose Studio:Your Uptown Base

The price is SAR 371
SAR 680 total
includes taxes & fees
7 Jul - 8 Jul
Montrose Studio:Your Uptown Base

Elegant 2BR Apartment w/ In-Unit Laundry

The price is SAR 402
SAR 827 total
includes taxes & fees
8 Jul - 9 Jul
Elegant 2BR Apartment w/ In-Unit Laundry

Majestic Modern Style|13 mins DT|4 mins Lake

9.2 out of 10, Wonderful, (9)
"Perfect for our short weekend stay. We walked to Ubered to local restaurants and bars. Checked out Andersonville. "
The price is SAR 263
SAR 839 total
includes taxes & fees
23 Jun - 24 Jun
Majestic Modern Style|13 mins DT|4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (29)
"Fun 1br stay. Great for a getaway or weekend stay."
The price is SAR 263
SAR 839 total
includes taxes & fees
23 Jun - 24 Jun
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

8.4 out of 10, Very Good, (7)
"Very nice cozy little apartment. Contactless check in and the instructions provided were clear and simple. Parked in a Spot Hero lot about a quarter mile north of the apartment. There were plenty of spots left when we got there and left so that was cheap and convenient. We only stayed here to sleep after a concert so we didn't really use any amenities or anything so I can't speak to that. There were some reviews about thin walls but the neighbors apparently weren't home or are very quiet because...
The price is SAR 263
SAR 839 total
includes taxes & fees
23 Jun - 24 Jun
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Bright & Modern Apt | Steps to Lake, Train, Food

10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised with easy (albeit somewhat tight) parking, minimal house rules and clean-up required, and a reasonable price. I would gladly stay again on a future trip to Chicago."
Bright & Modern Apt | Steps to Lake, Train, Food

Spacious 4BR Retreat - Chase E1

The price is SAR 694
SAR 1,675 total
includes taxes & fees
8 Jul - 9 Jul
Spacious 4BR Retreat - Chase E1

2BR/1BA North Shore Nest

The price is SAR 383
SAR 789 total
includes taxes & fees
7 Jul - 8 Jul
2BR/1BA North Shore Nest

Cozy 1BR Apt in Rogers Park

Cozy 1BR Apt in Rogers Park

Perfect 3BR Apt in Chicago

Perfect 3BR Apt in Chicago

Lovely 2BR Apartment with Equipped Kitchen

Lovely 2BR Apartment with Equipped Kitchen

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago

Chic apartment with fitness room and AC in beautiful Chicago

The price is SAR 369
SAR 1,145 total
includes taxes & fees
22 Jun - 23 Jun
Chic apartment with fitness room and AC in beautiful Chicago

Spacious 2BR Near Dining & Shops

Spacious 2BR Near Dining & Shops

2BR Getaway - Comfy & Ready

2BR Getaway - Comfy & Ready

3BR Spacious Apartment in Chicago

3BR Spacious Apartment in Chicago

Cozy studio in Andersonville Chicago

9.6 out of 10, Exceptional, (5)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is SAR 394
SAR 709 total
includes taxes & fees
22 Jun - 23 Jun
Cozy studio in Andersonville Chicago

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (1)
"The location was perfect. It was clean and just as pictured. For a studio, it had plenty of room. "
The price is SAR 488
SAR 898 total
includes taxes & fees
8 Jul - 9 Jul
Relaxing Chicago Studio

Sunlit Studio with City Charm - Lunt studio rep

Sunlit Studio with City Charm - Lunt studio rep
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.
Save an average of 15% on thousands of hotels when you're signed in

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 5299 accommodation choices including 2631 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: Cozy studio in Andersonville Chicago: Located in Chicago, 17.1 mi/27.5 km from the heart of Highwood. Includes free WiFi. Access to onsite laundry facilities is available on site. Luxurious 3 Bedroom Apartment in Chicago: Located 17.1 mi/27.5 km away in Chicago. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. 2-bedroom apartment just 2 minutes drive to Wrigley Field: Located in Chicago, 18.7 mi/30.2 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING: 17.9 mi/28.9 km away in Chicago. Free WiFi and separate dining areas are included. Serene 3-bedroom apartment in Chicago: Located in Chicago, 17.1 mi/27.5 km from Highwood. 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 Rosewood Beach. 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.