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Search and Rent Highwood Condos

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Condo Rentals in Highwood

Urban Chicago Escape ~ 1 Mi to Local Beaches!
Kitchen features a microwave, gas stove, and oven, along with a granite countertop and stainless steel sink.

Urban Chicago Escape ~ 1 Mi to Local Beaches!

9.4 out of 10, Exceptional, (20)
"We met friends for the weekend. This was such a fun, comfortable place to stay. Plus it was a 5 minute walk to the train station, which made sight seeing in Chicago so accessible! We would definitely stay again!"
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Walking distance to restaurants, shops and Lake Michigan,
Classic corner building with a central entrance, surrounded by a black iron fence and lush greenery.

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (183)
"We enjoyed our stay in Rogers Park. The property was nice and a welcome retreat at the end of the day. "
Walking distance to restaurants, shops and Lake Michigan,
Walk to Train: Convenient Skokie Condo!
Enjoy cooking in this fully equipped kitchen with a dining area and convenient washing machine.

Walk to Train: Convenient Skokie Condo!

2.0 star property
10.0 out of 10, Exceptional, (2)
"The condo was spacious and situated in a nice area. Place is located nearby the yellow Skokie CTA line to take you into the city for activities. Host was helpful and quick to respond to any questions we had."
Walk to Train: Convenient Skokie Condo!
Just remodeled apartment close to airport and mall
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and ample counter space.

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (11)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
$233 nightly
The price is $249
Aug 9 - Aug 10
Total includes taxes and fees
Just remodeled apartment close to airport and mall
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Relax in a serene outdoor space with a central water feature, surrounded by lush greenery and modern architecture.

Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago

10.0 out of 10, Exceptional, (26)
"Awesome stay!"
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.4 out of 10, Exceptional, (28)
"The place was super nice, very clean, and quiet. It was perfectly located for our needs. We were visiting my daughter and brand new granddaughter, and hope to make it our new home away from home when we visit."
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Prepare meals in a clean and functional kitchen with a stainless steel stove and ample natural light.

Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

9.8 out of 10, Exceptional, (18)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
Relax in this serene bedroom with a large bed, framed artworks, and a potted plant.

SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen

9.4 out of 10, Exceptional, (8)
"Place was as described and the check in/check out process was easy. Location was great as it was next to the train station and target for any necessities needed. House was clean provided enough space for a comfortable stay. Would recommend and stay again."
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
Walking distance to restaurants, shops and Lake Michigan,
Classic building with a central entrance and symmetrical facade, featuring a double door and series of windows.

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (205)
"Everything was as listed. "
Walking distance to restaurants, shops and Lake Michigan,
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Enjoy cooking in this well-equipped kitchen with a refrigerator, stove, dishwasher, and coffee maker.

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

9.6 out of 10, Exceptional, (24)
"Great location near Northwestern University. Plenty of on street parking for our group. Good communication with owner."
$453 nightly
The price is $515
Aug 19 - Aug 20
Total includes taxes and fees
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Wrigley 2 bedroom 2 bath with free parking & yard!
Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and refrigerator.

Wrigley 2 bedroom 2 bath with free parking & yard!

10.0 out of 10, Exceptional, (4)
"Great location and ease of getting around. Great amenities."
Wrigley 2 bedroom 2 bath with free parking & yard!
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
Enjoy a modern kitchen and dining area with a sleek design, gas stove, and round glass table.

"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

10.0 out of 10, Exceptional, (54)
"Great stay!"
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
Free Parking, Private Terrace Up to 10%off on 30day stay
Enjoy a convenient coffee break at the Dempster Street Station's drive-thru, surrounded by a beautifully maintained outdoor seating area.

Free Parking, Private Terrace Up to 10%off on 30day stay

10.0 out of 10, Exceptional, (38)
"Very convenient to bus stop, train station, and a few stores for essentials. A clean and comfortable apartment with a lovely little porch. I hope to stay here again!"
Free Parking, Private Terrace Up to 10%off on 30day stay
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a dining area with a table and vase of flowers.

Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

10.0 out of 10, Exceptional, (35)
"Wonderful location and home. Thanks to our hosts!"
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
PARKING, BALCONY near NAPA, UNIVERSITIES, RAVINIA, GOLFING & TRAIN to CHICAGO
Stroll through a tranquil outdoor oasis with a central water feature, surrounded by lush planters and a paved walkway.

PARKING, BALCONY near NAPA, UNIVERSITIES, RAVINIA, GOLFING & TRAIN to CHICAGO

10.0 out of 10, Exceptional, (14)
"Great location for us. Very clean, comfortable place . Would stay again."
PARKING, BALCONY near NAPA, UNIVERSITIES, RAVINIA, GOLFING & TRAIN to CHICAGO
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Cozy retreat with a rustic brick wall, a comfortable bed, and a wooden shelf.

Soft Suede and Warm Bricks at a Stylish Rogers Park Home

9.4 out of 10, Exceptional, (31)
"Beautiful and clean property!"
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Cozy 3BR on Chicago's North Side & Free Parking On-premises!
Enjoy cooking in this well-equipped kitchen with a gas stove, dishwasher, and granite countertop.

Cozy 3BR on Chicago's North Side & Free Parking On-premises!

10.0 out of 10, Exceptional, (2)
"Beautiful property. Great location with plenty of room for everyone. All the comforts of home. Would stay here again. "
Cozy 3BR on Chicago's North Side & Free Parking On-premises!
Spacious Skokie Retreat - 2BR/2BA - Mins to Chicago, mall & Train
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and dishwasher.

Spacious Skokie Retreat - 2BR/2BA - Mins to Chicago, mall & Train

10.0 out of 10, Exceptional, (1)
"Its good for a family of 4-5"
Spacious Skokie Retreat - 2BR/2BA - Mins to Chicago, mall & Train
Oakton St. Inn, Evanston near Northwestern, Loyola and Chicago
Enjoy cooking in this well-equipped kitchen with a central island and stainless steel appliances.

Oakton St. Inn, Evanston near Northwestern, Loyola and Chicago

10.0 out of 10, Exceptional, (11)
"The second floor flat was well lit with great space in the kitchen for cooking, nice place to eat overlooking the neighborhood, and a great place to sit and watch a movie or the game. Beds were comfortable and bathrooms were nice. Overall, a great place to stay for a visit to the area. "
Oakton St. Inn, Evanston near Northwestern, Loyola and Chicago
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover

2.0 star property
9.0 out of 10, Wonderful, (4)
"We rented this apartment for a concert at Wrigley Field during the hottest week of the year (June 26, 2025, iykyk). We loved it and would rent again! The air conditioning worked FANTASTIC, which was needed. There were tons of restaurants in the area. The apartment is about a 20 minute walk to Wrigley Field and about 30 steps from the Brown Line train. $5 to ride trains all day, made exploring Chicago easy. It wasn't hard to find parking nearby during any time of day or day of week (be warned,...
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
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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Top Highwood Hotel Reviews

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

10/10 Excellent
"Nice Hotel. Reasonable Price. Room was clean. Property could use updating. "
Carlo 5-night trip
Posted 22 hours ago
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove