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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Highwood apartments

Fridge, microwave, oven, stovetop

Apartment in Uptown

Majestic Modern Style|13 mins DT|4 mins Lake
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
The price is AED 185
AED 864 total
includes taxes & fees
22 Jan - 23 Jan
Majestic Modern Style|13 mins DT|4 mins Lake
Iron/ironing board, travel crib, WiFi, bed sheets

Apartment in Skokie

Chic Skokie Retreat - 1BR Unit in Skokie
2.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is AED 231
AED 607 total
includes taxes & fees
21 Jan - 22 Jan
Chic Skokie Retreat - 1BR Unit in Skokie
Interior

Apartment in Irving Park

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
The price is AED 314
AED 768 total
includes taxes & fees
20 Jan - 21 Jan
Pine Beam Sloth Apartment next to Blue Line
TV, offices

Apartment in North Park

Cozy 1BR Apartment Near Dining & Shops
10.0 out of 10, Exceptional, (1 review)
"Everything was perfectly designed. Sleek and Comfortable. Easy to access. Parking on the street next block. "
United States
Jill S.
The price is AED 231
AED 619 total
includes taxes & fees
20 Jan - 21 Jan
Cozy 1BR Apartment Near Dining & Shops
Terrace/patio

Apartment in Uptown

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
10.0 out of 10, Exceptional, (49 reviews)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is AED 286
AED 1,026 total
includes taxes & fees
1 Feb - 2 Feb
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Property grounds

Apartment in North Center

2-bedroom apartment just 2 minutes drive to Wrigley Field
2.0 star property
9.6 out of 10, Exceptional, (56 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is AED 426
AED 1,115 total
includes taxes & fees
25 Jan - 26 Jan
2-bedroom apartment just 2 minutes drive to Wrigley Field
Smart TV, books

Apartment in West Ridge

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
10.0 out of 10, Exceptional, (5 reviews)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is AED 314
AED 1,036 total
includes taxes & fees
20 Jan - 21 Jan
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
Outdoor dining

Apartment in Edgewater

Relaxing Chicago Studio
10.0 out of 10, Exceptional, (47 reviews)
"Had a great stay. Great location. "
United States
Justin
The price is AED 184
AED 521 total
includes taxes & fees
20 Jan - 21 Jan
Relaxing Chicago Studio
2 bedrooms, iron/ironing board, travel crib, WiFi

Apartment in Belmont Cragin

2BR Cozy & Functional Unit
10.0 out of 10, Exceptional, (1 review)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
The price is AED 253
AED 700 total
includes taxes & fees
1 Feb - 2 Feb
2BR Cozy & Functional Unit
TV, offices

Apartment in Edgewater

Stylish and Roomy 2BR in Chicago
9.0 out of 10, Wonderful, (14 reviews)
"Location was perfect for the weekend festivities. The unit was clean and well appointed. Communication with the host was easy and timely. "
United States
Maribeth
The price is AED 250
AED 695 total
includes taxes & fees
2 Feb - 3 Feb
Stylish and Roomy 2BR in Chicago
Private kitchen

Apartment in Rogers Park

Cozy apartment with AC and WiFi in awesome Chicago
9.2 out of 10, Wonderful, (7 reviews)
"clean and comfortable "
United States
Joseph S.
The price is AED 294
AED 1,024 total
includes taxes & fees
20 Jan - 21 Jan
Cozy apartment with AC and WiFi in awesome Chicago
TV, offices

Apartment in Rogers Park

Great Layout – Spacious 2BR Apt
10.0 out of 10, Exceptional, (5 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is AED 253
AED 700 total
includes taxes & fees
25 Jan - 26 Jan
Great Layout – Spacious 2BR Apt
Interior

Apartment in Albany Park

Comfortable 2BR Chicago Apt
9.6 out of 10, Exceptional, (4 reviews)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is AED 268
AED 717 total
includes taxes & fees
20 Jan - 21 Jan
Comfortable 2BR Chicago Apt
TV, offices

Apartment in Portage Park

Cozy 1-Bedroom Apartment
10.0 out of 10, Exceptional, (1 review)
"The place was great! It's stocked with the basics, bed and couch are comfy, and everything is clean. There were only a handful of times when I heard the upstairs neighbor, but nothing too crazy. The neighborhood itself is very cute and quiet, with good food and stores within walking distance. Street parking was easy. Thank you! "
United States
Sarah M.
The price is AED 231
AED 619 total
includes taxes & fees
20 Jan - 21 Jan
Cozy 1-Bedroom Apartment
Smart TV

Apartment in Barrington

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
9.8 out of 10, Exceptional, (7 reviews)
"Barrington was an adorable town tucked away just an hour out of Chicago. This property is the perfect spot for a getaway with your loved one. My boyfriend and I had an amazing weekend and will definitely stop by again in the future!"
United States
Cierra F.
The price is AED 463
AED 790 total
includes taxes & fees
20 Jan - 21 Jan
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
TV

Apartment in Avondale

Chic & Fully Furnished 2BR Apt!
10.0 out of 10, Exceptional, (2 reviews)
"Our stay was great! The apartment is very clean and comfortable. Nicely furnished. On a residential street in a lovely neighborhood. Wifi and A/C units worked well (we were there in August). We found street parking pretty easily. And Kristine was a really responsive host. Would absolutely stay again!"
United States
Stephanie D.
The price is AED 253
AED 700 total
includes taxes & fees
1 Feb - 2 Feb
Chic & Fully Furnished 2BR Apt!
Terrace/patio

Apartment in South Evanston

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
10.0 out of 10, Exceptional, (43 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is AED 314
AED 803 total
includes taxes & fees
25 Jan - 26 Jan
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Interior

Apartment in Highland Park

Stunning & Stylish Downtown Studio - Highland Park
2.0 star property
8.8 out of 10, Excellent, (6 reviews)
"The apartment was just as advertised and fit my needs. The A/C went down the first day and the host was extremely responsive and got it fixed right away. The location is perfect and and extremely convenient. 10/10 would stay again!"
United States
Rich K.
The price is AED 239
AED 584 total
includes taxes & fees
20 Jan - 21 Jan
Stunning & Stylish Downtown Studio - Highland Park
TV, offices

Apartment in West Dempster

Spacious 2BR Close to it All - Chic Apt in Skokie
8.0 out of 10, Very Good, (1 review)
"Nice apartment, good location for what I was in the area for. Unfortunately we couldn't get the radiators to turn on, but the building stayed relatively warm regardless."
United States
Rion B.
The price is AED 253
AED 688 total
includes taxes & fees
20 Jan - 21 Jan
Spacious 2BR Close to it All - Chic Apt in Skokie
2 bedrooms, iron/ironing board, travel crib, WiFi

Apartment in Albany Park

Warm & Stylish 2BR Apt
10.0 out of 10, Exceptional, (1 review)
"Met my expectations. Nice comfortable unit located in a great part of Chicago. Host was very responsive."
United States
Maureen B.
The price is AED 268
AED 717 total
includes taxes & fees
29 Jan - 30 Jan
Warm & Stylish 2BR Apt
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.
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Top Highwood Hotel Reviews

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Very convenient with short walk to the terminal. "
James 1-night trip
Posted 1 day ago
Hilton Chicago O'Hare Airport

Frequently asked questions

What's it like to stay at an apartment in Highwood?
You can search through 5 apartments in Highwood for your trip. Make time to visit the region's favorite places like Naval Base Great Lakes.
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: Relaxing Chicago Studio: Located in Chicago, 17.1 mi/27.5 km from the heart of Highwood. Includes separate dining areas and Smart TVs. 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. Nice 1BR Spot, Unwind & Relax: It's located in Chicago, 17.9 mi/28.8 km away. Charming Wrigleyville Home Close to the Cubs!: Located 19.2 mi/31 km away in Chicago. Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Cozy studio in Andersonville Chicago: Located in Chicago, 17.1 mi/27.5 km from Highwood. Includes free WiFi. Access to onsite laundry facilities is available on site.
How many apartments are there in Highwood?
Expedia has 5 apartments to book in 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 Northbrook Sports Complex, 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.