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Compare 44 Condo Rentals in Highland with updated reviews, rates, and availability.

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Open living room features vaulted ceilings and hardwood floors.
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
10.0 out of 10, Exceptional, (7)
"Great balcony view. Loved the massage chair after a day in the city. Easy pick up and drop off location for Uber. Easy ride to and from the city."
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
The Chic Urban Retreat Near the Lake!
Interior
The Chic Urban Retreat Near the Lake!
10.0 out of 10, Exceptional, (1)
"Loved the place - stayed for the Air Show and we were close enough to get everywhere quickly!"
The Chic Urban Retreat Near the Lake!
Historic Washington-Hyde Park Greystone
Living area
Historic Washington-Hyde Park Greystone
10.0 out of 10, Exceptional, (2)
"Was a great spot near Soldier Field for a concert. Casey and husband was super cool. Very nice place, comfortable beds, very accommodating Gave us good information for the area. will definitely come back. "
Historic Washington-Hyde Park Greystone
Bronzeville Manor walking distance to hospitals
Room
Bronzeville Manor walking distance to hospitals
10.0 out of 10, Exceptional, (11)
"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."
Bronzeville Manor walking distance to hospitals
Newly Built Condo: 5 Mi to Downtown Chicago!
Chicago Vacation Rental | 3BR | 2BA | Step-Free Access | 1,250 Sq Ft
Newly Built Condo: 5 Mi to Downtown Chicago!
10.0 out of 10, Exceptional, (2)
"I was pleased with the upscale interior and the neighborhood but sort of mislead of the distance to the United Convention Center. It was not accessible by metro train. Still, we were able to Uber to and from with safety late at night. There was difficulty accessing the key upon arrival and difficulty returning it to the lockbox. On the day of departure, I noticed a water leak from the vent in the master bathroom that appeared to have been there for a while. We were leaving that day, so that it...
Newly Built Condo: 5 Mi to Downtown Chicago!
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Bathroom
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
10.0 out of 10, Exceptional, (15)
"Have stayed here multiple times. We always have a good experience. It would have been very helpful to have kitchen towels. I do most of my own cooking & hand wash the dishes."
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
Dining
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
10.0 out of 10, Exceptional, (2)
"11 family members in Chicago for a wedding. Enough beds for everyone in the two condos located one above the other. Very convenient."
Lovely Quiet, Safe 6-Bedroom in 2 Condos Suite by McCormick Place and Midway!
Gorgeous N. Kenwood/Hyde Park
Private kitchen
Gorgeous N. Kenwood/Hyde Park
2.0 star property
10.0 out of 10, Exceptional, (1)
"Unit was very nice and spacious. Communication with owner throughout my stay was excellent. I will definitely consider this unit again my next trip to Chicago."
Gorgeous N. Kenwood/Hyde Park
Comfortable Condo in the Heart of Bronzeville by RedAwning
"Furniture","Indoors","Living Room","Table","Home Decor"
Comfortable Condo in the Heart of Bronzeville by RedAwning
5.0 out of 10, (2)
"There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!"
The price is AED 530
AED 1,651 total
includes taxes & fees
2 Oct - 3 Oct
Comfortable Condo in the Heart of Bronzeville by RedAwning
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
View from deck
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
10.0 out of 10, Exceptional, (12)
"We liked how clean and well decorated the condo was. The pool was nice, and the train close by was a bonus. We went to Indiana Dunes national park and to Chicago during our stay."
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
Spacious two bedroom condo with a cozy feel!
Living Space
Spacious two bedroom condo with a cozy feel!
8.0 out of 10, Very Good, (4)
"Very nice amenities. Comfortable beds."
Spacious two bedroom condo with a cozy feel!
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
View from property
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
10.0 out of 10, Exceptional, (2)
"Very nice"
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
Lovely 2 Bedroom Condo With Pool
Exterior
Lovely 2 Bedroom Condo With Pool
Lovely 2 Bedroom Condo With Pool
420 zen environment surrounded by boho chic decor~Luv Happii House.
Living area
420 zen environment surrounded by boho chic decor~Luv Happii House.
10.0 out of 10, Exceptional, (1)
"My stay at the Luv Happy House was the perfect getaway for my birthday. The house looks exactly like it is listed which is so beautiful! I loved everything about this place nd the host was very responsive, even when i called her at 11:00pm because I had a hard time finding the place. She directed me until i got there, I will definitely stay here again."
420 zen environment surrounded by boho chic decor~Luv Happii House.
A luxury vintage condo close to lakefront and minutes from downtown!
Living Room
A luxury vintage condo close to lakefront and minutes from downtown!
A luxury vintage condo close to lakefront and minutes from downtown!
Luxury Stay on UChicago Campus 11 min walk to hospitals
Living room
Luxury Stay on UChicago Campus 11 min walk to hospitals
10.0 out of 10, Exceptional, (1)
"We couldn't have found a better accommodation for our four-day visit to Hyde Park, than this newly renovated property on Ingleside. Literally a few minutes' walk from the quad of UofC, the three-bedroom, two full bathroom unit was more than ample space for our two couples hoping to have ease of access to the University and the restaurants and shops of Hyde Park. The modern kitchen had everything we needed, and the living room was spacious with study desk and entertainment seating. The whole...
Luxury Stay on UChicago Campus 11 min walk to hospitals
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
Living area
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
King Bed Suite | Indoor Pool. Free Breakfast.
Take a dip in the pool.
King Bed Suite | Indoor Pool. Free Breakfast.
King Bed Suite | Indoor Pool. Free Breakfast.
MODERN 2 BEDROOM CONDO! WHEN LUXURY & COMFORT MEET!
Exterior
MODERN 2 BEDROOM CONDO! WHEN LUXURY & COMFORT MEET!
8.8 out of 10, Excellent, (5)
"pictures do not do justice…nice place i especially loved the living room concept i would stay here again for sure"
MODERN 2 BEDROOM CONDO! WHEN LUXURY & COMFORT MEET!
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Primary bedroom with private en-suite full bathroom.
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
9.0 out of 10, Wonderful, (6)
"Arsene was excellent to work with. He met us at the condo and showed us everything. He was super responsive during our stay. Condo is located really close to University of Chicago, where our daughter had a college swim meet."
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
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Other property types in Highland

Congress Plaza Hotel
Exterior detail
Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (7836)
"Such an amazing historical hotel. Easily walked to things we had planned to visit. "
The price is AED 500
AED 601 total
includes taxes & fees
2 Oct - 3 Oct
Congress Plaza Hotel
River Hotel
Front of property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (3404)
"Great location for people watching and access to tourist attractions "
The price is AED 429
AED 515 total
includes taxes & fees
29 Sep - 30 Sep
River Hotel
Eurostars Magnificent Mile
Room
Eurostars Magnificent Mile
4.0 star property
8.6 out of 10, Excellent, (2558)
"The room"
The price is AED 735
AED 862 total
includes taxes & fees
23 Sep - 24 Sep
Eurostars Magnificent Mile
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

How much do condos in Highland cost?
You can expect to pay from to per night for condos in Highland. No matter your budget, an epic stay is a click away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Highland?
Highland has 44 condos. To help you book the perfect stay, use our filters to search for the must-have hotel amenities.
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