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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 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
Exterior

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

10.0 out of 10, Exceptional, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
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
9.8 out of 10, Exceptional, (6)
"My wife and I were attending a show and stayed for a night. It's fairly close to the Aragon Ballroom and has lots of dining options nearby. The host was attentive and easy to reach. He even shoveled the snow at 11pm; as it had snowed during the show and when it was over several inches had fallen. Well done sir, cleanest walk in the neighborhood.Everything in the apartment was clean and comfortable."
The price is AED 349
AED 950 total
includes taxes & fees
5 Mar - 6 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"First of all, the pictures does not do this place justice. It was so bright and sunny and well decorated. It was WELL stocked with anything you could think of. And our hostess was the mostess. Thank you again Tori for everything. I just loved the place! Easy parking as well, that's always a plus in my book!"
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Property grounds

The Holiday Lake House - 2br 2bth - 50 steps from the beach!

10.0 out of 10, Exceptional, (39)
"This was a great place to celebrate the holidays. Kitchen was well stocked with cookware and utensils to make Christmas dinner and we had plenty of room to gather for game night. Beds were comfy and all amenities were in good condition. The apartment looks brand new! Loved the shampoo/conditioner/soap dispensers in the shower! Will definitely be back next Christmas. Thanks for the hospitality!"
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

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

9.4 out of 10, Exceptional, (44)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (16)
"Great walkable location with easy access to everything. We appreciated the parking passes so much. Brian has a very nice set up eith ever3you need for a great weekend getaway. "
Charming Wrigleyville Home Close to the Cubs!
Cozy Nest in Chicago's Vibrant Lincoln Square
Fridge, microwave, oven, stovetop

Cozy Nest in Chicago's Vibrant Lincoln Square

10.0 out of 10, Exceptional, (56)
"This isn't the fanciest place we've stayed in Chicago but it's plenty nice and might be my favorite( we come often to visit our daughter so have sampled different properties and neighborhoods. Very clean, in a quiet neighborhood close to the shops and restaurants of Lincoln Square. Train is fairly close to the property but the sound didn't bother us. Liked that it was on two levels, so adult children could have their own space. Street parking was easy on the weekend; stickers available from...
Cozy Nest in Chicago's Vibrant Lincoln Square
1 Garage Spot Included - Near "L" Train - Highly Rated - North Center
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (12)
"Great time staying in a wonderful condo in terrific location. This was my second time here and I have no complaints. Tara was a great communicator. Highly recommend. "
1 Garage Spot Included - Near "L" Train - Highly Rated - North Center
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Fridge, microwave, oven, stovetop

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

10.0 out of 10, Exceptional, (24)
"Really nice unit. It was immaculately clean. The renovations are all fresh. The building was quiet and in a good location for my needs. Hosts communication was excellent. "
The price is AED 294
AED 732 total
includes taxes & fees
10 Mar - 11 Mar
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
Terrace/patio

Artistic Loft Rooftop Uptown Montrose Beach GymWFH

10.0 out of 10, Exceptional, (20)
"Fun 1br stay. Great for a getaway or weekend stay."
The price is AED 257
AED 821 total
includes taxes & fees
9 Mar - 10 Mar
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking
Fridge, microwave, oven, stovetop

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
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Interior

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.0 out of 10, Very Good, (16)
"Ckean and affordable."
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Cozy W Front Porch DT Libertyville near Naval Base
Miscellaneous

Cozy W Front Porch DT Libertyville near Naval Base

9.4 out of 10, Exceptional, (10)
"Friendly neighborhood, close to base and many restaurants and shop..... definitely go to The Green Room!!!!!!"
Cozy W Front Porch DT Libertyville near Naval Base
Stunning & Stylish Downtown Studio - Highland Park
Fridge, microwave, oven, stovetop

Stunning & Stylish Downtown Studio - Highland Park

2.0 star property
The price is AED 294
AED 606 total
includes taxes & fees
20 Mar - 21 Mar
Stunning & Stylish Downtown Studio - Highland Park
Corporate Housing by MGM
Pool

Corporate Housing by MGM

2.0 star property
7.8 out of 10, Good, (6)
"Came here for a navy graduation, amazing stay. This place is very clean and neat, they provide basic utensils (ie. forks, spoons, knives) along with pots and pans and other useful kitchen items. Communication with host was clear and check in instructions were very simple to follow and remember. Location also very close to grocery stores, restaurants, and the mall. Overall loved this place and if I came to Chicago again I would choose this place again! "
The price is AED 505
AED 1,082 total
includes taxes & fees
5 Mar - 6 Mar
Corporate Housing by MGM
Great for families DT Libertyville Near Naval Base
Miscellaneous

Great for families DT Libertyville Near Naval Base

9.8 out of 10, Exceptional, (11)
"Everything was well-equipped and just as the listing described. The host was friendly and responsive. The location is very close to the quaint downtown shops and an easy drive to and from Naval Station Great Lakes. There are large stores for groceries and other needs nearby. "
Great for families DT Libertyville Near Naval Base
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
1 bedroom, iron/ironing board, WiFi, bed sheets

Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.

10.0 out of 10, Exceptional, (28)
"My daughter and I loved our time here. From the first steps through the gate we felt comfortable and welcome! Great bed and linens, beautiful bathroom, and excellent kitchenette. Everything we needed was there and the charm and coziness of this little carriage house really had us wishing our stay was longer!. We will absolutely look forward to staying here again! 10/10 recommend!"
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
Relaxing 2BR Apartment in Lively West Rogers Park
Beach

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
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

8.8 out of 10, Excellent, (18)
"Place was really nice. Property manager was very kind and friendly! Responded in a timely manner. The place was nice and clean. Felt very comfortable during our stay. "
The price is AED 360
AED 930 total
includes taxes & fees
12 Mar - 13 Mar
Bright Garden Studio
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

Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (24)
"The property listing was exactly as described. Very clean and quite spacious. We arrived at 530 pm and found adequate street parking. The beds were comfortable, the kitchen was stocked with key necessities and the bathrooms provided plenty of towels and basic toiletries. Our host was responsive with any concerns too. I would definitely recommend this property!"
Great 3 bedroom rental unit near Logan Square
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (16)
"Great walkable location with easy access to everything. We appreciated the parking passes so much. Brian has a very nice set up eith ever3you need for a great weekend getaway. "
Charming Wrigleyville Home Close to the Cubs!
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

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

9.4 out of 10, Exceptional, (44)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking
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 5045 accommodation choices including 2576 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: 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. Roscoe Village Inn -Guesthouse - Walk to Chicago’s Wrigley Field: Located 19.3 mi/31.1 km away in Chicago. Charming Wrigleyville Home Close to the Cubs!: It’s situated in Chicago, 19.2 mi/31 km away. Includes Smart TVs. The Holiday Lake House - 2br 2bth - 50 steps from the beach!: 16 mi/25.8 km away in Chicago. Free WiFi, private patios, and jetted bathtubs are included. Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!: Located in Chicago, 17.4 mi/28.1 km from Highwood. Includes free WiFi, outdoor space, and private yards. Access to free breakfast 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 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.