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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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

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, (46)
"This property is very clean and very cozy. The location is great, except at night, I was able to hear the train and highway traffic. My husband wasn't bothered at all. We still liked it and suited our needs. The amenities were excellent. There's plenty of parking. "
Chic, Cozy home, by Blue Line Train Stop + Free parking
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, (8)
"The property is very quiet, clean, well appointed, and is in a great location. It’s only a 3 minute walk to the Brown Line which easily gets you downtown in half an hour and not worry about parking. I did notice the absence of a microwave which would have been an added convenience. Overall, it suited my needs perfectly and will consider it again if I get back to Chicago."
The price is AED 327
AED 904 total
includes taxes & fees
10 Apr - 11 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (17)
"Great neighborhood. Free and easy parking. "
Charming Wrigleyville Home Close to the Cubs!
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
Fridge, microwave, oven, stovetop

Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94

10.0 out of 10, Exceptional, (3)
"This is the perfect place for a couple to stay for a weekend in the Windy City! It has everything you need, and youre close to the big attractions! Parking can be a little tricky, but the fact that its free helps a lot! Toby is a wonderful host. You'll feel taken care of, and enjoy your time at this property!"
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Terrace/patio

Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!

9.8 out of 10, Exceptional, (17)
"The two bedroom apartment was clean and comfortable"
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Property grounds

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover

8.8 out of 10, Excellent, (8)
"This lovely apartment was a great location for our family. Close to shops and restaurants. Easy walk to the Red Line train. The place was well stocked with bedding and the mattresses were quite comfy. We enjoyed cooking and hanging out in the living area. "
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is AED 298
AED 855 total
includes taxes & fees
15 Apr - 16 Apr
Bright Garden Studio
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Pool

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (96)
"We had an amazing stay at Jamie’s place. Quiet location, great host, and lovely accommodations. If you’re visiting Chicago, highly recommend staying at Jamie’s. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Fridge, microwave, oven, stovetop

Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square

3.0 star property
9.8 out of 10, Exceptional, (10)
"We live in a very rural area and wanted to see Chicago. This property was better than advertised! It was a short walk to the L for easy commuting to the Loop, where we walked to Field and Shedd's. We enjoyed the parks and neighborhoods by the apartment- all very safe. Apartment was spacious, clean, quiet. Kitchen stocked well for cooking meals. We would stay here again."
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Beach

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

10.0 out of 10, Exceptional, (217)
"Our group consisted of two couples and this place was perfect for us. Very comfortable, kitchen is well equipped with everything you could need. "
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Great Location-Beautiful Friendly Andersonville Neighborhood
Smart TV, books

Great Location-Beautiful Friendly Andersonville Neighborhood

10.0 out of 10, Exceptional, (178)
"Fantastic location and wonderful property. Walking distance to lots of restaurants, cute stores, the Swedish Museum, and the train to go downtown. We loved the charm of this older home. Everything was very clean, the beds were soft, and the shower great! I was a little concerned about on street parking but we were always able to find a spot near by. "
Great Location-Beautiful Friendly Andersonville Neighborhood
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
Terrace/patio

Artistic Loft Rooftop Uptown Montrose Beach GymWFH

10.0 out of 10, Exceptional, (22)
"My stay was very comfortable and matched the listing accurately. I did notice some dog hair from a previous guest, which is understandable given how challenging it can be to clean thoroughly. Overall, the space was clean and pleasant. Thank you for a nice experience!"
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
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, (11)
"The house was cozy, clean and comfortable. I would highly recommend staying here to anyone. Third bedroom is downstairs...which was a surprise. But all was good."
Cozy W Front Porch DT Libertyville near Naval Base
"Hope of Evanston" 180°view, 2BDR +2Bath Urban luxury
Interior

"Hope of Evanston" 180°view, 2BDR +2Bath Urban luxury

10.0 out of 10, Exceptional, (14)
"The property is beautiful, clean, warm and welcoming. Great location. Convenient, secure parking. Could not have been better. This will be our go to for accommodations when we are in Chicago. "
"Hope of Evanston" 180°view, 2BDR +2Bath Urban luxury
Elegant 3 Bedroom and 1 Bath Apartment
3 bedrooms, desk, iron/ironing board, free WiFi

Elegant 3 Bedroom and 1 Bath Apartment

9.0 out of 10, Wonderful, (10)
"Very nice place - can easily fit quite a few people! Host was very accommodating, place was clean and comfortable. My friends and I had a great time! "
Elegant 3 Bedroom and 1 Bath Apartment
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, (171)
"Great experience and location. Worked perfect for our needs "
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Smart TV

Cozy 2BR/1BA Garden Apartment Near Lincoln Square

8.0 out of 10, Very Good, (8)
"The place was clean but very cold even when the heat was requested to be turned up. Probably just part of being in a basement. Overall, it was a great place but wish there was a Keurig and complimentary coffee. Coffee was the one thing I didn’t think about bringing. "
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Luxury 5Bed 2Bath Apt w/Parking
Fridge, microwave, oven, stovetop

Luxury 5Bed 2Bath Apt w/Parking

Luxury 5Bed 2Bath Apt w/Parking
Chic studio in Loyola University with WiFi, fitness room, steps from the lake
Fridge, oven, stovetop, coffee/tea maker

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

9.0 out of 10, Wonderful, (4)
"It's a new place with comfortable but bare bones furniture. A few more tables or dressers wouldn't hurt. The area is great with lots of restaurant options. Street parking was generally easy. Nice place."
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

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, (8)
"The property is very quiet, clean, well appointed, and is in a great location. It’s only a 3 minute walk to the Brown Line which easily gets you downtown in half an hour and not worry about parking. I did notice the absence of a microwave which would have been an added convenience. Overall, it suited my needs perfectly and will consider it again if I get back to Chicago."
The price is AED 327
AED 904 total
includes taxes & fees
10 Apr - 11 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is AED 298
AED 855 total
includes taxes & fees
15 Apr - 16 Apr
Bright Garden Studio
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (50)
"Clean. Quiet. Comfortable. As advertised. "
The price is AED 400
AED 727 total
includes taxes & fees
28 Apr - 29 Apr
Master qtr close to nature & easy urban facilities
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 4937 accommodation choices including 2463 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: 2-bedroom apartment just 2 minutes drive to Wrigley Field: Situated in Chicago, 18.7 mi/30.2 km from the heart of Highwood. Includes free WiFi and Smart TVs. Bright Garden Studio: Located 13.6 mi/21.8 km away in Evanston. Private patios, fireplaces, and separate dining areas are included. Chic, Cozy home, by Blue Line Train Stop + Free parking: 17.8 mi/28.7 km away in Chicago. Free WiFi, private balconies, and Smart TVs are included. Charming Wrigleyville Home Close to the Cubs!: It’s located in Chicago, 19.2 mi/31 km from Highwood. Includes Smart TVs.
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 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.