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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

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
Private kitchen

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
9.6 out of 10, Exceptional, (5)
"One of the most beautiful rentals I've stayed in. Also, when there was a hiccup in the booking process, the owner communicated directly with me right away, coming to a solution that made everyone happy. A very lovely experience all around. "
The price is AED 624
AED 1,302 total
includes taxes & fees
12 Feb - 13 Feb
2-bedroom apartment just 2 minutes drive to Wrigley Field
NEW, clean & sunny, 2bd, private deck, 15min to Wrigley!
Living area

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!
Terrace/patio

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
Private kitchen

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

9.4 out of 10, Exceptional, (42)
"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!
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!
Chic apartment in phenomenal Chicago with WiFi, AC
Interior

Chic apartment in phenomenal Chicago with WiFi, AC

8.8 out of 10, Excellent, (6)
"I was really impressed with the decor and layout. The TV wasn’t working but other than that the experience was great"
Chic apartment in phenomenal Chicago with WiFi, AC
Cozy Nest in Chicago's Vibrant Lincoln Square

Cozy Nest in Chicago's Vibrant Lincoln Square

10.0 out of 10, Exceptional, (55)
"We returned to our old neighborhood of Lincoln Square after 15 years for the Frozen Confines hockey games at Wrigley. This home was a perfect base for all our activities! We were cozy and had fun playing foosball, air hockey and board games at the large dining room table! Almir was very responsive and directions were clear and accurate! Highly recommend!"
Cozy Nest in Chicago's Vibrant Lincoln Square
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

10.0 out of 10, Exceptional, (11)
"Tara’s apartment is beautiful!! Exactly as shown in listing! Tara was very responsive and gave great directions! Check in and out we’re very easy. Would definitely stay there again!!"
1 Garage Spot Included - Near "L" Train - Highly Rated - North Center
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Bedroom

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

10.0 out of 10, Exceptional, (22)
"Me and my daughter felt more than accepted and had a great time while moving her to college. Thank you for giving us a sense of home while away. "
The price is AED 275
AED 712 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Artistic Loft Rooftop Uptown Montrose Beach GymWFH

Artistic Loft Rooftop Uptown Montrose Beach GymWFH

10.0 out of 10, Exceptional, (18)
"This property is located only a few blocks from various public transit stops which gave us great access to Downtown Chicago without having to drive.Additionally, the property was clean and the perfect size for a couple. Everything was included for us to prepare our own meals and hang out inside since we visited in the winter. We would certainly consider this location again if we visit the city in the future!"
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
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
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
Living area

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.0 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

Cozy W Front Porch DT Libertyville near Naval Base

9.4 out of 10, Exceptional, (9)
"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
Interior

Stunning & Stylish Downtown Studio - Highland Park

2.0 star property
The price is AED 239
AED 551 total
includes taxes & fees
3 Mar - 4 Mar
Stunning & Stylish Downtown Studio - Highland Park
Corporate Housing by MGM

Corporate Housing by MGM

2.0 star property
8.6 out of 10, Excellent, (4)
"Overall enjoyed our stay! Well stocked and nice decorated. Clear check-in and check-out instructions. Our stay went smoothly. "
The price is AED 480
AED 1,074 total
includes taxes & fees
2 Feb - 3 Feb
Corporate Housing by MGM
Great for families DT Libertyville Near Naval Base

Great for families DT Libertyville Near Naval Base

9.6 out of 10, Exceptional, (10)
"This apt is perfect. Stayed for Navy graduation and it’s located 15mins from Base. You will be surprised as to how big and comfortable this place is. We did the “locals” thing and walked to the little town of Libertyville for the day. A few miles away is the more modern side of town. The apt was stocked with all we needed for our stay. Highly recommend this apt and management was awesome. "
Great for families DT Libertyville Near Naval Base
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
1

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
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

3-bedroom house WiFi in lovely Waukegan Near Gurnee
Private kitchen

3-bedroom house WiFi in lovely Waukegan Near Gurnee

2.0 star property
4.4 out of 10, (13)
"Cute little house at all the necessities convenient to Naval base where we spent most of our time"
3-bedroom house WiFi in lovely Waukegan Near Gurnee
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, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Bright Garden Studio
Interior

Bright Garden Studio

8.8 out of 10, Excellent, (16)
"We had a great stay in this Evanston lower level studio apartment while in town for our reunion and Homecoming weekend at Northwestern. The studio is clean, nicely decorated, good amenities, and conveniently located to both the NU campus and downtown Chicago. Having a dedicated parking spot was awesome too, as the off-street parking fills up quickly in the evening. My only recommendation would be replacing the really firm mattress with a softer one, or a memory foam topper. All in all we had...
The price is AED 209
AED 760 total
includes taxes & fees
2 Feb - 3 Feb
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.

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 5026 accommodation choices including 2530 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: Roscoe Village Inn -Guesthouse - Walk to Chicago’s Wrigley Field: Situated in Chicago, 19.3 mi/31.1 km from the heart of Highwood. 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. Bright Garden Studio: It’s situated in Evanston, 13.6 mi/21.8 km away. Includes private patios, fireplaces, and separate dining areas.
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.