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Compare 47 Condo Rentals in Highland with updated reviews, rates, and availability.

Modern Condo-Obama & University of Chicago Area
Dining

Modern Condo-Obama & University of Chicago Area

9.0 out of 10, Wonderful, (2)
"Nice place. Small, but good for our purposes. Communication with the owner was real easy. "
Modern Condo-Obama & University of Chicago Area
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, (15)
"Our host was amazing. Every question was answered within minutes. The condo itself is fantastic. The massage chair was a great bonus. Wonderful place to stay especially if you are going to the McCormick Convention Center. A five minute drive. Would stay here again. "
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
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!
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!
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Living area

Spacious 2 bedroom 2 bath 10 Minutes to Down Town

9.8 out of 10, Exceptional, (19)
"Loved the split bedroom arrangements. Property clean, kitchen great for cooking and chilling. We had a rainy day… great place to hang out. Neighbors were very kind and helpful."
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
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!
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Interior

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

6.6 out of 10, (4)
"The property was exactly as pictured. Once we mastered the front gate, the rest of the trip was a breeze! It’s an ideal rental for two or three people."
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
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, (13)
"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!
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 1,023
AED 1,285 total
includes taxes & fees
5 Jan - 6 January 2025
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

LakeHouse
Game room

LakeHouse

10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse
Cozy Home Sweet Homewood.
Living area

Cozy Home Sweet Homewood.

10.0 out of 10, Exceptional, (15)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

9.2 out of 10, Wonderful, (56)
"We recently rented this home for our church's women's fall spiritual retreat. This stay for our group of 21 ladies was more than we expected. We chose this home for its size, proximity to the shore, and great accommodations. Upon our arrival we were pleasantly surprised to find the house had been recently updated. It was absolutely beautiful...bright, serene, and peaceful! The cleanliness of the home was great! The attention to detail was appreciated. I love a well stocked kitchen and this...
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
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 1,023 to AED 1,023 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 47 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?
Expedia can help you locate cheap condos in Highland. To find your dream stay in a couple of clicks, use our convenient filter tool to refine your search by amenities, star rating and budget.