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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 310 Apartments in Highwood with updated reviews, rates, and availability.

Cozy studio in Andersonville Chicago
Iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.6 out of 10, Exceptional, (4)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is AED 239
AED 512 total
includes taxes & fees
9 Jun - 10 Jun
Cozy studio in Andersonville Chicago
Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (4)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
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, (19)
"Great time and location. "
The price is AED 426
AED 1,098 total
includes taxes & fees
8 Jun - 9 Jun
2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Exterior

North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

10.0 out of 10, Exceptional, (106)
"Really enjoyed our stay. Parking was easy and we could walk to restaurants. Felt very safe and the neighborhood was welcoming. Would stay again."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
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, (53)
"This property was clean, and the host provided clear instructions for access. I reached out to the host/owner and they were immediately responsive. Overall a great experience."
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, (22)
"This place was perfect for us, and right where we needed it to be. "
Charming Wrigleyville Home Close to the Cubs!
Corporate Housing by MGM
Fridge, microwave, oven, stovetop

Corporate Housing by MGM

8.4 out of 10, Very Good, (7)
"We stayed here for a week for our sons Navy Graduation, 2/20/25...It was 12 mins from base, convenient, and although some reviews have that it was a little noisey, it was actually very quiet for us..quiet when we went."
The price is AED 671
AED 1,174 total
includes taxes & fees
30 Jun - 1 Jul
Corporate Housing by MGM
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (23)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is AED 389
AED 999 total
includes taxes & fees
16 Jun - 17 Jun
Bright Garden Studio
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Bright & Modern Apt | Steps to Lake, Train, Food
Fridge, microwave, oven, stovetop

Bright & Modern Apt | Steps to Lake, Train, Food

10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised with easy (albeit somewhat tight) parking, minimal house rules and clean-up required, and a reasonable price. I would gladly stay again on a future trip to Chicago."
The price is AED 657
AED 1,204 total
includes taxes & fees
16 Jun - 17 Jun
Bright & Modern Apt | Steps to Lake, Train, Food
Serene 3-bedroom apartment in Chicago
Smart TV

Serene 3-bedroom apartment in Chicago

10.0 out of 10, Exceptional, (2)
"I wish we had stayed longer!"
Serene 3-bedroom apartment in Chicago
Haus Of Hues: MDRN Bright Peaceful Private Apt
Fridge, microwave, oven, stovetop

Haus Of Hues: MDRN Bright Peaceful Private Apt

2.0 star property
9.2 out of 10, Wonderful, (12)
"Appreciated every little detail of this place. Thank you"
The price is AED 907
AED 1,775 total
includes taxes & fees
10 Jun - 11 Jun
Haus Of Hues: MDRN Bright Peaceful Private Apt
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Beach nearby

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

9.2 out of 10, Wonderful, (5)
"Everything was above expectations except the entry system. Three times during our 7 week stay the code to the outside door was changed and we got no advance warning. Luckily the manager was easy to reach and resolved the issue pronto. Otherwise it was a great stay in a great neighborhood."
The price is AED 650
AED 1,350 total
includes taxes & fees
13 Jun - 14 Jun
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Adorable 1BR Apartment in Evanston
Fridge, microwave, oven, stovetop

Adorable 1BR Apartment in Evanston

2.5 star property
8.6 out of 10, Excellent, (11)
"Great stay"
Adorable 1BR Apartment in Evanston
"Faith of Evanston" 180°view, 2BDR +2Bath Urban luxury
Interior

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

10.0 out of 10, Exceptional, (11)
"Great place to stay with family when traveling!"
"Faith of Evanston" 180°view, 2BDR +2Bath Urban luxury
Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV
Private kitchen

Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV

9.0 out of 10, Wonderful, (2)
"I enjoyed my stay in Rogers Park. The apartment was clean, convenient and comfortable. "
Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV
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
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Terrace/patio

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (29)
"Fun 1br stay. Great for a getaway or weekend stay."
The price is AED 878
AED 1,669 total
includes taxes & fees
13 Jun - 14 Jun
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Comfort/Clean!: Free Parking 15 min ORD/Downtown3
Fridge, microwave, oven, stovetop

Comfort/Clean!: Free Parking 15 min ORD/Downtown3

8.6 out of 10, Excellent, (16)
"The place was clean and cozy. "
Comfort/Clean!: Free Parking 15 min ORD/Downtown3
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, (224)
"Great rental, lovely, easy in and out."
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and 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.
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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 5256 accommodation choices including 2614 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: Cozy studio in Andersonville Chicago: Located in Chicago, 17.1 mi/27.5 km from the heart of Highwood. Includes free WiFi. Access to onsite laundry facilities is available on site. Luxurious 3 Bedroom Apartment in Chicago: Located 17.1 mi/27.5 km away in Chicago. Amenities include Smart TVs. Access to onsite laundry facilities is available on site. 2-bedroom apartment just 2 minutes drive to Wrigley Field: Located in Chicago, 18.7 mi/30.2 km away. Includes free WiFi and Smart TVs. Access to onsite laundry facilities is available on site. Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING: 17.9 mi/28.9 km away in Chicago. Free WiFi and separate dining areas are included. Chic, Cozy home, by Blue Line Train Stop + Free parking: Located in Chicago, 17.8 mi/28.7 km from Highwood. Includes free WiFi, private balconies, and Smart TVs. Access to onsite laundry facilities 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 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.