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

Bronzeville Manor walking distance to hospitals
Room
Bronzeville Manor walking distance to hospitals
10.0 out of 10, Exceptional, (14)
"The host is very kind and helpful, and the place is roomy and luxurious (we got upgraded to the penthouse before our stay). The neighborhood is quiet and we had no trouble finding a parking spot for the car. If you ever need a place to stay in Chicago, this is the place! 10/10 experience!"
Bronzeville Manor walking distance to hospitals
Modern Condo-Obama & University of Chicago Area
Exterior
Modern Condo-Obama & University of Chicago Area
10.0 out of 10, Exceptional, (1)
"Great place!"
Modern Condo-Obama & University of Chicago Area
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
Marina
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
♛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!
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, (12)
"First of all, Keeva was an amazing host. Very thoughtful & very responsive. The neighborhood was extremely quiet & peaceful, not far from most of the places we wanted to go. The massage chair was AMAZING. I wish I had one at my house, I actually fell asleep in it as it was so relaxing! The pictures don’t do it justice, honestly I wish I had taken a video of the bathroom sinks, I’ve never seen anything like them before. Absolutely gorgeous. Check in & out was super easy. 100% would stay here...
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
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
LONG STAY, 4 bd, Free Park, 2 miles to Hyde Park
Living area
LONG STAY, 4 bd, Free Park, 2 miles to Hyde Park
10.0 out of 10, Exceptional, (1)
"We had a great time visiting Chicago. The property was well designed and cozy, a home I'd live in. The host was very nice, responsive, and accommodating. Would stay there again on another visit!"
LONG STAY, 4 bd, Free Park, 2 miles to Hyde Park
The Chic Urban Oasis Near the Lake!
Interior
The Chic Urban Oasis 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 Oasis Near the Lake!
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!
Historic Washington-Hyde Park Greystone
Interior
Historic Washington-Hyde Park Greystone
10.0 out of 10, Exceptional, (3)
"The apartment was very nice, well decorated and equipped, thoroughly cleaned and easy to access. Will definitely stay there again if I'm in the area!"
Historic Washington-Hyde Park Greystone
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, (2)
"The condo was excellent. Would definitely rent again. Check in was easy and location great. Thank you. "
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.
The price is AED 1,093
AED 1,375 total
includes taxes & fees
8 Dec - 9 Dec
King Bed Suite | Indoor Pool. Free Breakfast.
Cozy Beautiful Condo
Living area
Cozy Beautiful Condo
Cozy Beautiful Condo
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!
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 Highland

Skyline Views, Hot Tub, Beachfront, Lavish Kitchen at Dunetop Villa
Skyline Views, Hot Tub, Beachfront, Lavish Kitchen at Dunetop Villa
9.2 out of 10, Wonderful, (45)
"Our family had a very good time enjoying house beach and national park "
Skyline Views, Hot Tub, Beachfront, Lavish Kitchen at Dunetop Villa
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Room
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
9.4 out of 10, Exceptional, (12)
"Thank you for the great stay. I really appreciate the little touches like the bath bomb. Much needed. Communication was great. Good location to stay. "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
forrestville home
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (66)
"Rented with Valane for the marathon weekend. It was clean, quiet, away from the hustle of the city. It was super easy to navigate to expo, start lines, and sites. Loved jot beong couped up in a hotel room for the weekend Highly recommend Thank you so much for the great stay"
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
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?
Prepare to pay from AED 1,093 to AED 1,093 per night for condos in Highland. Whatever your budget, the perfect stay is a click away on Expedia. These prices were 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?
Use up your vacation days and pick from 44 condos in Highland. For business travel, a family getaway and everything in between, Expedia can help you find the right place in just a few clicks.
Why book your condo in Highland with Expedia?
Getting away should be a piece of cake, so if you’re on the lookout for condos at an affordable price, Expedia can help. Save cash and pick something small and cozy, or book a 5-star condo and spoil the ones you love most. Our search filters make it easy to find a stay in Highland that checks your boxes.
How can I find cheap condos in Highland?
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