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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 49 Condo Rentals in Highland with updated reviews, rates, and availability.

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
Modern Condo-Obama & University of Chicago Area
Dining

Modern Condo-Obama & University of Chicago Area

9.0 out of 10, Wonderful, (4)
"short visit to go to appointments at U Chicago med center. "
Modern Condo-Obama & University of Chicago Area
The Chic Urban Oasis Near the Lake!
Interior

The Chic Urban Oasis Near the Lake!

6.8 out of 10, (3)
"First thing we had an issue with gaining access to the building due to weather conditions and the key boxes being out in the elements. Once we gained entry, there were some issues with things in the unit but overall the unit was aesthetically pleasing to be in. Outside of the weather affecting our stay, we still enjoyed our stay and the experience. This was not our first ABB experience and it will not be our last. I would recommend this place to others. It had enough sleeping spaces for up to 9...
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)
"Just what we were looking for "
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St
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!
Comfortable Condo in the Heart of Bronzeville by RedAwning
"Home Decor","Furniture","Indoors","Living Room","Table"

Comfortable Condo in the Heart of Bronzeville by RedAwning

5.4 out of 10, (3)
"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 SAR 592
SAR 1,524 total
includes taxes & fees
25 Feb - 26 Feb
Comfortable Condo in the Heart of Bronzeville by RedAwning
Gorgeous N. Kenwood/Hyde Park
Interior

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
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, (16)
"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
5 Mi to Dtwn Chicago: Newly Built Condo
Chicago Vacation Rental | 3BR | 2BA | Step-Free Access | 1,250 Sq Ft

5 Mi to Dtwn Chicago: Newly Built Condo

9.6 out of 10, Exceptional, (4)
"Overall, it is a great property...it is spacious, clean and nicely decorated. It definitely was a comfortable location for me and my family while we were in Chicago."
5 Mi to Dtwn Chicago: Newly Built Condo
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
♛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 2 Bedroom Condo With Pool
Exterior

Lovely 2 Bedroom Condo With Pool

Lovely 2 Bedroom Condo With Pool
Bronzeville Manor walking distance to hospitals
Room

Bronzeville Manor walking distance to hospitals

9.6 out of 10, Exceptional, (15)
"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 Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Interior

Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

2.5 star property
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
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!
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.
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.
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.
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

Comfort Inn Chicago Wind Creek Casino
Front of property

Comfort Inn Chicago Wind Creek Casino

2.5 star property
6.0 out of 10, (2)
The price is SAR 335
SAR 378 total
includes taxes & fees
26 Mar - 27 Mar
Comfort Inn Chicago Wind Creek Casino
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home

8.8 out of 10, Excellent, (27)
"Lovely space to red a big group to gather,plus smaller living spaces fur sac mallet subgroups. "
Beachfront Villa + Addition, Skyline views, Hot Tubs, Luxury Smart Home
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, (57)
"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 SAR 592 to SAR 592 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 49 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.