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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 61 Condo Rentals in Highwood with updated reviews, rates, and availability.

Urban Chicago Vacation Rental Condo Near Beach!
Beach nearby

Urban Chicago Vacation Rental Condo Near Beach!

9.2 out of 10, Wonderful, (17)
"The property was just as advertised. Street parking was not a problem. Had some issues with the window blinds, but the property owners were quick to respond to our concern. "
Urban Chicago Vacation Rental Condo Near Beach!
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, (24)
"Two night stay. Arrived day late though so actually one night stay.As add says, parking tight. We found parking garage on Clark st and used Uber. Very convenient. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
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, (105)
"We stayed for a Cubs game and the home did NOT disappoint. It was BETTER than we expected. The place is completed remodeled and really nice! The mattresses were super comfy, access was easy, and the TV had apple TV. The neighborhood is super safe and has lots of stores (coffee esp) within walking distance. I highly rec this VRBO! "
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
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
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, (13)
"My family had a long visit to Chicago and this apartment was perfect! It looks just as it appears in pictures. Very comfortable! We hope to stay here 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,
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (198)
"Everything was as listed. "
Walking distance to restaurants, shops and Lake Michigan,
Bright 2BR Apt w/ Private Entrance & Laundry
Interior

Bright 2BR Apt w/ Private Entrance & Laundry

2.0 star property
8.0 out of 10, Very Good, (2)
"Stayed 3 nights visiting my son. Good location, large apt., nicely decorated. I wish the tub/shower had a grab bar. The jacuzzi tub has a high profile and is difficult for older adults to step in and out. It was quiet inside--even the nearby train was hard to hear. I did trip several times on the drain cover right outside the entry door. Be careful!"
Bright 2BR Apt w/ Private Entrance & Laundry
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
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Interior

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

2.0 star property
9.8 out of 10, Exceptional, (9)
"Comfortable accommodations with separate bedrooms for 5 traveling friends. Although the apartment can accommodate 8, there were only dishes for 6, so we had to run the dishwasher after every meal. Very clean. Frustrating WIFI: none in parking garage nor lobby. Had to go outside of the building to access info about check in. "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
2 bedrooms, desk, iron/ironing board, free WiFi

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

10.0 out of 10, Exceptional, (22)
"Clean and convenient! Great responsiveness from the host and was very accommodating. I would stay again! "
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
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, (29)
"Well maintained/ updated space in turn of the century brownstone. The listing was spot on, we will book again if we are in town and it is available. "
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
2 bedrooms, desk, iron/ironing board, WiFi

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

9.6 out of 10, Exceptional, (4)
"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
The Bright Retreat in Andersonville
Fridge, microwave, oven, stovetop

The Bright Retreat in Andersonville

9.8 out of 10, Exceptional, (56)
"We enjoyed the location of the apt to the grocery, stores restaurants and the CTA rail and bus. There were dishes and cookware to use during our stay. The neighbors were very quite and the neighborhood was peaceful. "
The Bright Retreat in Andersonville
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, (37)
"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
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
3 bedrooms, desk, iron/ironing board, free WiFi

Soft Suede and Warm Bricks at a Stylish Rogers Park Home

9.4 out of 10, Exceptional, (29)
"Thoroughly enjoyed our stay in Rogers Park! Place was clean, well-stocked, and very comfortable. Host was in close communication. Off-street parking appreciated. Location across the street from grocery store and easy access to Chicago and Evanston. Highly recommend!"
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (44)
"In for the weekend for the football game. Great location, super clean, well stocked and comfortable. "
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
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
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
Just remodeled apartment close to airport and mall
Private kitchen

Just remodeled apartment close to airport and mall

9.8 out of 10, Exceptional, (9)
"Ihor was very nice and the communication was good. He responded pretty quickly. The place was cute and clean. Neighborhood was good and pleasant. "
The price is SAR 563
SAR 970 total
includes taxes & fees
29 Apr - 30 Apr
Just remodeled apartment close to airport and mall
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
9.8 out of 10, Exceptional, (11)
"It was such an amazing property. Short walk to Wrigley which was perfect for me and my friends!!!!!! Will be booking again in the future"
The price is SAR 334
SAR 919 total
includes taxes & fees
28 Apr - 29 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, (21)
"Great Location"
The price is SAR 300
SAR 873 total
includes taxes & fees
29 Apr - 30 Apr
Bright Garden Studio
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, (173)
"Well equipped APT on quiet streetOn street parking was no problemNice new appliancesBeds comfortableLinens niceGreat trip!Thank you!"
Roscoe Village Inn -Guesthouse - Walk to Chicago's 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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