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 356
SAR 665 total
includes taxes & fees
14 Jul - 15 Jul
Uptown Studio Gem Sum

Montrose Studio:Your Uptown Base

The price is SAR 356
SAR 665 total
includes taxes & fees
16 Jul - 17 Jul
Montrose Studio:Your Uptown Base

Elegant 2BR Apartment w/ In-Unit Laundry

The price is SAR 368
SAR 814 total
includes taxes & fees
12 Aug - 13 Aug
Elegant 2BR Apartment w/ In-Unit Laundry

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

8.6 out of 10, Excellent, (14)
"Loved the space, nice decor, clean. Perfect for 2 people."
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (34)
"This was convenient and check-in process was easy. We would stay here again."
The price is SAR 263
SAR 894 total
includes taxes & fees
13 Jul - 14 Jul
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

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 281
SAR 916 total
includes taxes & fees
16 Jul - 17 Jul
Majestic Modern Style|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."
The price is SAR 746
SAR 1,334 total
includes taxes & fees
11 Aug - 12 Aug
Bright & Modern Apt | Steps to Lake, Train, Food

Spacious 4BR Retreat - Chase E1

2.0 out of 10, (1)
"3 hours before we were supposed to check-in they canceled. They had my cell phone and didn't contact me. I had messaged them to get check in information and was only told at that time the place was now unavailable. For something as important as cancelling last minute they should have called, messaged and emailed. They had no problem requiring me via my cell phone to give them not only give them the names and ages of every guest staying but a picture of my passport and CC. Was this just a scam to...
The price is SAR 653
SAR 1,608 total
includes taxes & fees
28 Jul - 29 Jul
Spacious 4BR Retreat - Chase E1

Great Layout – Spacious 2BR Apt

The price is SAR 345
SAR 747 total
includes taxes & fees
15 Jul - 16 Jul
Great Layout – Spacious 2BR Apt

Cozy 1BR Apt in Rogers Park

Cozy 1BR Apt in Rogers Park

Lovely 2BR Apartment with Equipped Kitchen

Lovely 2BR Apartment with Equipped Kitchen

2BR Getaway - Comfy & Ready

The price is SAR 345
SAR 747 total
includes taxes & fees
13 Jul - 14 Jul
2BR Getaway - Comfy & Ready

Spacious 2BR Near Dining & Shops

The price is SAR 345
SAR 752 total
includes taxes & fees
22 Jul - 23 Jul
Spacious 2BR Near Dining & Shops

3BR Spacious Apartment in Chicago

"The property was OK, save for a lot of mold in the bathroom. Anybody booking with this property manager needs to be prepared for a lot of texts from a lot of random area codes requesting personal information (age, occupation, residence, multiple selfies). If you're young and don't think twice about giving away all your information online, it's not a problem. But it's jarring otherwise."
The price is SAR 608
SAR 1,125 total
includes taxes & fees
28 Jul - 29 Jul
3BR Spacious Apartment in Chicago

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (10)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is SAR 319
SAR 616 total
includes taxes & fees
15 Jul - 16 Jul
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 281
SAR 639 total
includes taxes & fees
14 Jul - 15 Jul
Relaxing Chicago Studio

Sunlit Studio with City Charm - Lunt studio rep

Sunlit Studio with City Charm - Lunt studio rep

Delightful 1BR Apt in Ravenswood

The price is SAR 356
SAR 702 total
includes taxes & fees
13 Jul - 14 Jul
Delightful 1BR Apt in Ravenswood

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago

1BR Apartment in Rogers Park

10.0 out of 10, Exceptional, (1)
"Clean up to date place in quiet neighborhood. "
The price is SAR 334
SAR 680 total
includes taxes & fees
14 Jul - 15 Jul
1BR Apartment in Rogers Park
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 5297 accommodation choices including 2638 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: Luxurious 3 Bedroom Apartment in Chicago: Located in Chicago, 17.1 mi/27.5 km from the heart of Highwood. Includes Smart TVs. Access to onsite laundry facilities is available on site. Cozy studio in Andersonville Chicago: Located 17.1 mi/27.5 km away in Chicago. Amenities include free WiFi. Access to onsite laundry facilities is available on site. Charming 3-bedroom apartment with AC and WiFi in Waukegan.: It's situated in Waukegan, 9.5 mi/15.2 km away. Includes free WiFi, private balconies, and separate dining areas. 2-bedroom apartment just 2 minutes drive to Wrigley Field: Located 18.7 mi/30.2 km away in Chicago. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Nice 1BR Spot, Unwind & Relax: It's situated in Chicago, 17.9 mi/28.8 km from Highwood.
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.