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Compare 285 Apartments in Highwood with updated reviews, rates, and availability.

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Living area

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.4 out of 10, Very Good, (14)
"The property was excellent, for my stay "
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen

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

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Charming Wrigleyville Home Close to the Cubs!
Bedroom 1

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (14)
"This place was perfect for us, and right where we needed it to be. "
Charming Wrigleyville Home Close to the Cubs!
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover
Our converted storefront condo has high ceilings and large windows, lending the living area an airy and open feel

PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

9.4 out of 10, Exceptional, (26)
"Nice open space with large bedrooms. Quiet and clean! Perfect location to walk to local restaurants and shops "
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover
Regal Stylish Uptown Loft Beachfront RooftopWFHGym

Regal Stylish Uptown Loft Beachfront RooftopWFHGym

8.6 out of 10, Excellent, (10)
"Although it's posted as small, it had plenty of room for us. VERY clean and comfortable, and walking distance to all that we needed. Will definitely stay here again"
The price is AED 176
AED 704 total
includes taxes & fees
30 Dec - 31 Dec
Regal Stylish Uptown Loft Beachfront RooftopWFHGym
Spirit of Evanston
Living area

Spirit of Evanston

9.6 out of 10, Exceptional, (5)
"Great stay. Beds were comfortable. Apartment was very clean and well appointed. "
Spirit of Evanston
Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym

Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym

9.4 out of 10, Exceptional, (14)
"we really enjoyed our stay here!! it was super nice and the bed was comfortable. there were a lot of useful amenities which we really liked. the location was convenient because it had a lot of food/bar options and was right by the music venue we went to. will definitely stay here again if we come back to chicago. thank you to the host for this little find!! "
Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym
1 Garage Spot Included - Near "L" Train - Highly Rated - North Center
Centrally located in the North Center neighborhood of Chicago's northside.

1 Garage Spot Included - Near "L" Train - Highly Rated - North Center

9.8 out of 10, Exceptional, (10)
"Our stay was phenomenal! It couldn’t have been more perfect. The apartment has everything you need. It is very clean, cozy, organized and quiet.There are tons of restaurants, shopping and things to do within waking distance. Tara was extremely accommodating and responsive. I will surely recommend this to friends and family and I will be booking again in the future. "
1 Garage Spot Included - Near "L" Train - Highly Rated - North Center
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
9.4 out of 10, Exceptional, (3)
"Clean , beautiful home."
The price is AED 441
AED 1,062 total
includes taxes & fees
1 Jan - 2 January 2025
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chic apartment in phenomenal Chicago with WiFi, AC
Interior

Chic apartment in phenomenal Chicago with WiFi, AC

9.4 out of 10, Exceptional, (3)
"Check in prices was a breeze, superb communication at all times and we were very pleased with our stay here"
Chic apartment in phenomenal Chicago with WiFi, AC
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Private kitchen

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

10.0 out of 10, Exceptional, (166)
"Fantastic location and an outstanding host! I had an amazing stay. The space was ideal for my needs, offering a comfortable and convenient setting to assist my daughter with her wedding preparations. It had everything I was looking for—well-equipped with great amenities and in a prime location. The property was spotless, peaceful, and provided everything needed for a smooth and enjoyable experience. Easy street parking was always available! I highly recommend this place to anyone looking for a...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
3BR Spacious Home Away From Home
Our home away from home

3BR Spacious Home Away From Home

10.0 out of 10, Exceptional, (29)
"Everything was very nicely laid out and organized. Everything was pretty clean. We did not realize that it was just the one floor though and that there would be people above us. That could be better advertised in the description of the property. Other than that it was very good. "
3BR Spacious Home Away From Home
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
Full kitchen with all high end appliances

Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field

9.8 out of 10, Exceptional, (37)
"Spent the weekend in Chicago, could not have been happier with this location and was a great spot to call home for a few days!"
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking
Living area

8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking

8.0 out of 10, Very Good, (7)
"Cute with extra bedding for everyone."
8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking
10 minutes to the lake! Family-sized Apt with free parking.
Private kitchen

10 minutes to the lake! Family-sized Apt with free parking.

10.0 out of 10, Exceptional, (4)
"Clean and nice property and value for the money for the price"
10 minutes to the lake! Family-sized Apt with free parking.
Relaxing 2BR Apartment in Lively West Rogers Park
Living area

Relaxing 2BR Apartment in Lively West Rogers Park

9.0 out of 10, Wonderful, (2)
"My husband and I had a wonderful stay at this VRBO. It was just as depicted and and more. Perfect location, within walking distance of a lot of bars and especially the beach which we loved. The host was welcoming, professional, and helpful throughout the entire stay. The VRBO was clean, nicely decorated, inviting, and easy to access/ locate. Looking forward to coming back to Chicago one day and possibly staying here again."
Relaxing 2BR Apartment in Lively West Rogers Park
Beautifully Styled Apartment in South East Evanston
Dining

Beautifully Styled Apartment in South East Evanston

10.0 out of 10, Exceptional, (2)
"Very quiet. Perfect for a weekend in Evanston Appreciated the parking. "
Beautifully Styled Apartment in South East Evanston
ALL NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
Living area

ALL NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!

ALL NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
Chic studio in Loyola University with WiFi, fitness room, steps from the lake
Room

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

8.0 out of 10, Very Good, (2)
"Great location, walkable to everything you could need. Kitchen was great made a few meals for us there. Good size tv small desk iron n hair dryer on site fitness equipment was great. Very easy digital entry. Communication was great arranged for airport pickup and drop off. Worked w me when my flight was delayed. So appreciative to all the assistance. "
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.
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Other property types in Highwood

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

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

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Breathtaking home close to Schaumburg, Chicago
Exterior

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (45)
"We had unexpected changes last minute for Thanksgiving and our Host was so great and accommodating. The space was roomy and beautiful with the rooms flowing into each other so little groups of people could talk and nosh and enjoy the food and company. The light coming in from the windows and the backyard is a little piece of nature to enjoy. At our request, our wonderful host even snuck in to start a fire for us in the firepit, making it even more homey. My husband, myself, my sister, and my...
Breathtaking home close to Schaumburg, Chicago
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
First floor living room with leather couch, smart cable TV, and Alexa speaker.

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (120)
"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & 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.

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 4912 accommodation choices including 2434 apartments. While in the region, visit favorite sights 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?
Listed below are some of the top apartments in the area: Chic, Cozy home, by Blue Line Train Stop + Free parking: Situated in Chicago, 17.8 mi/28.7 km from the heart of Highwood. Includes free WiFi, private balconies, and Smart TVs. Charming Wrigleyville Home Close to the Cubs!: It’s situated in Chicago, 19.2 mi/31 km away. Includes Smart TVs. PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover: 19.4 mi/31.2 km away in Chicago.
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 Ravinia Park. 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.