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Compare 279 Apartments in Highwood with updated reviews, rates, and availability.

Beautiful apartment in peaceful Elk Grove
Lobby
Beautiful apartment in peaceful Elk Grove
Beautiful apartment in peaceful Elk Grove
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, (163)
"The location is close to the bus, and then easy to the Metro. It was about a 40ish min travel to the Art Institute when we were there. Roscoe Village is picturesque. There is a Starbucks at the end of the street if you want your pumpkin spice latte, but they've also got plenty of local talent- the owner of Rudy's Bakery (try the butter cookies YUM!!)-was lovely. There were plenty of other places--we just didn't have time! We arrived on Halloween; the entire neighborhood came out on their front...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.6 out of 10, Exceptional, (34)
"The house & the apartment were very clean & cute. Neighborhood was nice & felt safe. My only complaints were that we would’ve liked more than 2 bath towels for two people for 3 days. Also, it was very warm in the apartment (no air conditioning), but who could’ve known it would be 80 degrees in mid-October. Thank goodness there was one fan provided."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
Flooring,Chair,Furniture,Living Room,Room
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
8.4 out of 10, Very Good, (16)
"The apartment suited our needs. We were in town to take care of some family business. Apartment was spacious and the location was perfect for us. Plenty of shopping and restaurants nearby."
Enjoy Evanston! Slow Down After a Busy Day Sight Seeing - Walking Distance from Public Transportation by AllSet Turnover
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO
Lovely living room with sofa sleeper.
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO
8.4 out of 10, Very Good, (10)
"It was a good place to stay for fanexpo "
Lovely 2 bedrooms apartment 10min from O'HARE CHICAGO
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
Comfy Avondale Flat - Sleeps 4
Comfy Avondale Flat - Sleeps 4
8.6 out of 10, Excellent, (10)
"We booked this place because we (two people) were working from home while visiting. The WiFi was enough for both of us to get all our work done, which was great. The space itself is fine. No razzle dazzle, but the Ms Pac Man machine ended up being a nice addition to our late nights. We really enjoyed the neighborhood, close proximity to restaurants and bars (definitely check out Central Park!)"
The price is SAR 169
SAR 765 total
includes taxes & fees
25 Nov - 26 Nov
Comfy Avondale Flat - Sleeps 4
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Bedroom
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
10.0 out of 10, Exceptional, (19)
"Imani’s apartment is in a great location and was sparkling clean with a very comfortable bed and couch. It appears to be freshly renovated. Check in was simple and easy. Imani is prompt to reply to questions and we would definitely stay at her place again."
The price is SAR 301
SAR 760 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Cozy w/ 3 Kings Beds & Front Porch! ★ Walk to Libertyville ★ Near Naval Base
Living area
Cozy w/ 3 Kings Beds & Front Porch! ★ Walk to Libertyville ★ Near Naval Base
10.0 out of 10, Exceptional, (3)
"Was a great stay. Was very quick responding to questions. Was quick drive to RTC from the house. Plenty to do within walking distance. "
Cozy w/ 3 Kings Beds & Front Porch! ★ Walk to Libertyville ★ Near Naval Base
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Living area
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
10.0 out of 10, Exceptional, (12)
"The management (Michelle) is very good at this property. It was clean and well maintained. If you need anything she gets it for you immediately. I will be back! Beautifully furnished, a nice balcony and the pool and deck area are lovely."
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Spacious 4-bedroom apartment with fitness room, WiFi in delightful Chicago
Room
Spacious 4-bedroom apartment with fitness room, WiFi in delightful Chicago
2.0 star property
4.0 out of 10, (4)
"The space is a second story apartment of a duplex. Check in is odd as they just leave a key behind a statue in front of the building. Not very secure. However, the area felt safe. Upon arrival there were no sheets or towels. We communicated this with the host the next day and they were quick to respond and rectify the issue. If you are looking for many beds on a budget as we were. It will do the job, but do not expect much more."
The price is SAR 1,503
SAR 2,049 total
includes taxes & fees
15 Nov - 16 Nov
Spacious 4-bedroom apartment with fitness room, WiFi in delightful Chicago
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Terrace/patio
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (34)
"Very clean and well thought out/supplied apartment on a lovely street a 30 second walk to Lake Michigan. There are 2 bedrooms, one larger master with en suite bathroom, and a second full bathroom and smaller bedroom. The unit is on the bottom floor so windows are high. Diane is friendly and responsive. The walk along the beach & out to an old lighthouse was a bonus. The street has mature trees and people walking dogs. There is a 7-11 on the corner and several restaurants walking distance. ...
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Charming Wrigleyville Home Close to the Cubs!
Bedroom 1
Charming Wrigleyville Home Close to the Cubs!
9.2 out of 10, Wonderful, (11)
"Fantastic neighborhood and a great little apartment. "
Charming Wrigleyville Home Close to the Cubs!
Chic Studio - In Downtown Highland Park, by Metra
Room
Chic Studio - In Downtown Highland Park, by Metra
8.4 out of 10, Very Good, (9)
"Overall my husband and I were happy with the studio apt. Communication with the host was easy and the place was clean and had all the amenities we needed during our stay. The place was centrally located with easy access to shops/restaurants as well as the Metra system to take us into Chicago. The one drawback is that there are no windows but the skylight adds enough natural light to the space and we were there to sightsee and not stay for extended periods in the apartment."
The price is SAR 485
SAR 821 total
includes taxes & fees
15 Nov - 16 Nov
Chic Studio - In Downtown Highland Park, by Metra
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood
Exterior
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood
7.6 out of 10, Good, (5)
"What a lovely place to stay! "
Retro 2 bedroom bungalow in Chicago's Avondale neighborhood
"Bliss of Evanston" 180°view, 2BDR +2Bath UrbanLux
Living area
"Bliss of Evanston" 180°view, 2BDR +2Bath UrbanLux
10.0 out of 10, Exceptional, (20)
"Nice Condo, central to Northwestern U. and the great neighborhoods in the area. "
"Bliss of Evanston" 180°view, 2BDR +2Bath UrbanLux
DT Libertyville Home ★ Near Naval Base ★ Arcade Pac Man & Air Hockey & PingPong
Living area
DT Libertyville Home ★ Near Naval Base ★ Arcade Pac Man & Air Hockey & PingPong
9.0 out of 10, Wonderful, (12)
"Very quick response at 12:30 am when we couldn’t get our code to work. Automatically let us in so we weren’t stuck outside in the cold and dark! Really great communication throughout our stay. "
DT Libertyville Home ★ Near Naval Base ★ Arcade Pac Man & Air Hockey & PingPong
10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT
Living area
10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT
8.6 out of 10, Excellent, (11)
"Close to metro station for riding into the city! Had all of the things my family needed to prepare meals, wash clothes, bathe and get plenty of rest during our trip 👍"
10-15 MIN FROM O'HARE CHICAGO-LOVELY 3BEDROOMS GARDEN APARTMENT
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
Living Room,Room,Indoors,Furniture,Couch
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
9.4 out of 10, Exceptional, (17)
"Nice Place ,.exactly as advertised "
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
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
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

Roxan Corner
Room
Roxan Corner
8.4 out of 10, Very Good, (28)
"Just what I needed. The property was clean and the neighborhood is quiet. I would definitely stay again."
Roxan Corner
Walking distance to restaurants, shops and Lake Michigan,
Large kitchen with open floor plan, hardwood floor throughout.
Walking distance to restaurants, shops and Lake Michigan,
9.6 out of 10, Exceptional, (171)
"Very easy to find. The host was friendly and was easy to communicate with. The condo was clean and and felt very safe. "
Walking distance to restaurants, shops and Lake Michigan,
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Terrace/patio
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (34)
"Very clean and well thought out/supplied apartment on a lovely street a 30 second walk to Lake Michigan. There are 2 bedrooms, one larger master with en suite bathroom, and a second full bathroom and smaller bedroom. The unit is on the bottom floor so windows are high. Diane is friendly and responsive. The walk along the beach & out to an old lighthouse was a bonus. The street has mature trees and people walking dogs. There is a 7-11 on the corner and several restaurants walking distance. ...
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
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 4859 accommodation choices including 2425 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: The Holiday Lake House - 2br 2bth - 50 steps from the beach!: Situated in Chicago, 16 mi/25.8 km from the heart of Highwood. Includes free WiFi, private patios, and jetted bathtubs. Charming Wrigleyville Home Close to the Cubs!: Located 19.2 mi/31 km away in Chicago. Amenities include Smart TVs. Chic, Cozy home, by Blue Line Train Stop + Free parking: It’s situated in Chicago, 17.8 mi/28.7 km away. Includes free WiFi, private balconies, and Smart TVs. Roscoe Village Inn | Guesthouse | Walk to Chicago’s Wrigley Field: It’s situated in Chicago, 19.3 mi/31.1 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 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.