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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 297 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, (45)
"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, (16)
"Really nice location and a good place to stay. There's not a full kitchen but there is a kitchenette. We were out and about most of the time so that was no problem for us. Great neighborhood. "
Charming Wrigleyville Home Close to the Cubs!
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, (7)
"This place was perfect for our overnight stay in Chicago! Thank you to the owners for making everything super easy and smooth. "
The price is SAR 371
SAR 971 total
includes taxes & fees
16 Mar - 17 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
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, (93)
"Great place for me to stay for work travel! Bed is cozy and Jamie does a fantastic job making guests feel welcome and comfortable. Location was super cute as well. I would definitely stay here again. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
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, (214)
"Beautiful property.. very responsive host .. above and beyond what we expected.. and Peefect location for us .. near our daughter’s new Roger’s park apartment !! Highly recommen "
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
3 BR / 2 BTH unit steps to the beach and close to Loyola
Terrace/patio

3 BR / 2 BTH unit steps to the beach and close to Loyola

10.0 out of 10, Exceptional, (27)
"The description about the property was very accurate. Very nice and clean. The kitchen was well stocked with cookware. I highly recommend this place. The pr"
3 BR / 2 BTH unit steps to the beach and close to Loyola
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
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
Elegant Style Loft Montrose Beach Rooftop WFH Gym
Terrace/patio

Elegant Style Loft Montrose Beach Rooftop WFH Gym

9.4 out of 10, Exceptional, (18)
"We rented this loft for a weekend trip. I thought check in process was a lot of steps having to download an app to get the check in information. The room loft was nice, but you could tell it had cheaper furniture. Bed was not comfortable and pillows were very flat like feathers. Shower did not have a liner and was ground level so water got on the floor easily. Shower head was not great and pressure was bad Overall it has fine for a weekend, and a good location close to a lot of things. "
The price is SAR 225
SAR 781 total
includes taxes & fees
17 Mar - 18 Mar
Elegant Style Loft Montrose Beach Rooftop WFH Gym
"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
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!
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 SAR 300
SAR 751 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
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
Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR/2BA Apartment in Chicago
Fridge, microwave, oven, stovetop

Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR/2BA Apartment in Chicago

9.8 out of 10, Exceptional, (17)
"We like the area and it feels safe there. We would stay there again, but we did see one cockroach in the kitchen, and you would need to wash some of the dishes you pull out of the cupboard. The apartment is spacious and accommodated our group well. The beds are comfy, but the king bed lacked a top sheet. Design tip: put floor and table lamps in the living area instead of just the overhead light. Couch and TV were awesome."
Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR/2BA Apartment in Chicago
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
Terrace/patio

Artistic Loft Rooftop Uptown Montrose Beach GymWFH

10.0 out of 10, Exceptional, (21)
"The property has everything you need for a comfortable stay. It was clean, quiet, everything looks like in the photos. There is a good work space, which was important to us. The location is good, close to the beach, shops and restaurants. It was not noisy, we slept well. We received answers to our questions very quickly."
The price is SAR 266
SAR 831 total
includes taxes & fees
23 Mar - 24 Mar
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
Haus Of Hues: MDRN Bright Peaceful Private Apt
Fridge, microwave, oven, stovetop

Haus Of Hues: MDRN Bright Peaceful Private Apt

2.0 star property
10.0 out of 10, Exceptional, (6)
"Craig was very responsive to any questions we had. Duplex is located in a great neighborhood. Easy street parking. We had everything we needed for a atay. eeverything "
The price is SAR 649
SAR 1,474 total
includes taxes & fees
16 Mar - 17 Mar
Haus Of Hues: MDRN Bright Peaceful Private Apt
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
Smart TV, DVD player

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
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
10.0 out of 10, Exceptional, (8)
"Very comfortable property close to some nice restaurants and ample shopping. Surprisingly quite at night enabled a great nights sleep."
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
Outdoor dining

The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.

10.0 out of 10, Exceptional, (99)
"Maia took great care of us, and offers a great place to stay. It’s exactly as listed and wonderful amenities, freshly laundered linens, and soft towels. Highly recommend!"
The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
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

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, (45)
"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
Great 3 bedroom rental unit near Logan Square
Interior

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (25)
"The property is as described and was perfect for our stay. David answered all of our questions promptly. Would definitely recommend this host and property."
Great 3 bedroom rental unit near Logan Square
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, (7)
"This place was perfect for our overnight stay in Chicago! Thank you to the owners for making everything super easy and smooth. "
The price is SAR 371
SAR 971 total
includes taxes & fees
16 Mar - 17 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
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 4938 accommodation choices including 2439 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. 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. Charming Wrigleyville Home Close to the Cubs!: It’s situated in Chicago, 19.2 mi/31 km away. Includes Smart TVs. Bright Garden Studio: 13.6 mi/21.8 km away in Evanston. Private patios, fireplaces, and separate dining areas 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 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.