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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 41 Condo Rentals in Highwood with updated reviews, rates, and availability.

Pet-Friendly Urban Chicago Vacation Rental Condo
Beach nearby

Pet-Friendly Urban Chicago Vacation Rental Condo

9.2 out of 10, Wonderful, (14)
"Great place to stay. Close to everything. Nice and clean "
Pet-Friendly Urban Chicago Vacation Rental Condo
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, (102)
"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
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (196)
"Great property and easy process to check in/out. Lots of space and privacy. It was easy to get around and explore the city. "
Walking distance to restaurants, shops and Lake Michigan,
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (22)
"Property was in a good area, less than 15 min to our destination. Plenty of restaurants and shopping nearby. Mark communication was veey good as well. "
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Terrace/patio

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, (28)
"It was clean and in a great neighborhood. Only had trouble finding parking but still was an amazing trip. Would definitely recommend."
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Interior

"Melody of Evanston" 3BD, 2BA UrbanLux Condo

2.0 star property
10.0 out of 10, Exceptional, (7)
"The property was wonderful! It was clean and located perfectly for getting around the north shore. We enjoyed our visit!! "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Free Parking, Private Terrace Up to 10%off on 30day stay
Exterior

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

10.0 out of 10, Exceptional, (35)
"Had nice weekend stay in Mark’s property. The place was very clean and the beds were comfortable. Mark was responsive and the one issue we had was resolved handily. Designated parking spot was a plus but we also found street parking easily for a second car. We did not cook but there seemed to be adequate supplies for that. Location was great; close to restaurants and shopping and easy access to the interstate. We would stay here again. "
Free Parking, Private Terrace Up to 10%off on 30day stay
The Bright Retreat in Andersonville
Fridge, microwave, oven, stovetop

The Bright Retreat in Andersonville

9.8 out of 10, Exceptional, (54)
"This condo was a wonderful place to stay. The location is very close to the redline CTA, as well as to the quaint Andersonville, full of nice restaurants and bars. It felt safe, in a quiet neighborhood. We would definitely stay here again."
The Bright Retreat in Andersonville
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Smart TV

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

9.8 out of 10, Exceptional, (12)
"Everything went well. Will stay again."
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
2 bedrooms, iron/ironing board, WiFi, bed sheets

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

10.0 out of 10, Exceptional, (22)
"We were visiting our nephew, who lives around the block from this rental, so we didn't spend a lot of time in the rental, but it was absolutely sparkling clean, well-appointed, and lovely. We will definitely book it again. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
TV

Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover

9.0 out of 10, Wonderful, (10)
"The apartment needs a deep cleaning. It’s been awhile. Coffee mugs were filthy — took a huge amount of time/effort to clean them. Dishes and utensils were not clean - someone when through the steps putting them in the dw but they were dirty with dried-on food. Very thoughtful chargers and night background devices. Was noisy in the morning and night so great! Great location for groceries. Great coffee maker. So close to being great. "
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
For up to 6 Spacious lovely Chicago-style 3-BDR condo. Safe & quiet neighborhood
Fridge, microwave, oven, stovetop

For up to 6 Spacious lovely Chicago-style 3-BDR condo. Safe & quiet neighborhood

8.6 out of 10, Excellent, (17)
"Beautiful-friendly place "
For up to 6 Spacious lovely Chicago-style 3-BDR condo. Safe & quiet neighborhood
Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w/parking
Interior

Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w/parking

10.0 out of 10, Exceptional, (5)
"Our stay in Evanston was awesome. Our unit was spacious, roomy, clean and had everything we needed. The location in Evanston was close to our event venue in Chicago plus near downtown Evanston as well. It was also great to walk to Lake Michigan and nearby restaurants. We greatly enjoyed our stay and would happily stay there again."
Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w/parking
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Fridge, microwave, oven, dishwasher

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (25)
"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
Bright 2BR Apt w/ Private Entrance & Laundry
Aerial view

Bright 2BR Apt w/ Private Entrance & Laundry

2.0 star property
8.0 out of 10, Very Good, (1)
Bright 2BR Apt w/ Private Entrance & Laundry
Soft Leather and Warm Bricks at a Stylish Rogers Park Home
Smart TV, stereo

Soft Leather and Warm Bricks at a Stylish Rogers Park Home

10.0 out of 10, Exceptional, (30)
"My family and I had a great stay at The Clark. This is a great, clean and cozy apartment with bonus amenities. Quality matresses, appliances, bluetooth speakers, and kitchenware. Master shower was clean, with plenty of towels. The kitchen and the beautiful wood countertop island served as a great area to congregate with my family. The check in was smooth, as our host, Lilian, provided access information prior to our arrival. She also made sure to check in with us during our stay to see how we...
Soft Leather and Warm Bricks at a Stylish Rogers Park Home
10 min walk to Stevenson Convention Center
Smart TV, books

10 min walk to Stevenson Convention Center

8.4 out of 10, Very Good, (5)
"Good "
10 min walk to Stevenson Convention Center
Studio- King Bed| HDTV| Airport| Safe Neighborhood
Smart TV

Studio- King Bed| HDTV| Airport| Safe Neighborhood

10.0 out of 10, Exceptional, (1)
Studio- King Bed| HDTV| Airport| Safe Neighborhood
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (22)
"We could not have asked for a better host & the place was awesome. Thank you"
The price is SAR 604
SAR 1,530 total
includes taxes & fees
30 Mar - 31 Mar
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
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
Fridge, microwave, oven, stovetop

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.

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