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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 57 Condo Rentals in Highland with updated reviews, rates, and availability.

Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop

Modern Condo-Obama & University of Chicago Area

9.2 out of 10, Wonderful, (5)
"Property was very well kept and accommodated us well. We didn’t spend much time there as we were out most of the day but it was nice to come back to a place like this."
Modern Condo-Obama & University of Chicago Area
Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
Terrace/patio

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.
Smart TV, books

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.
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
Property grounds

♛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!
Gorgeous N. Kenwood/Hyde Park
Fridge, microwave, oven, stovetop

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
Smart TV

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
Luxury Waterfront 2 Bedroom Condo by Lake Michigan
Outdoor dining

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
Comfortable Condo in the Heart of Bronzeville by RedAwning
Fridge, microwave, oven, coffee/tea maker

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!"
Comfortable Condo in the Heart of Bronzeville by RedAwning
5 Mi to Dtwn Chicago: Newly Built Condo
Fridge, microwave, stovetop, dishwasher

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
The Chic Urban Oasis Near the Lake!
Beach

The Chic Urban Oasis Near the Lake!

7.6 out of 10, Good, (4)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Fridge, microwave, oven, stovetop

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!
Fridge, microwave, oven, stovetop

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
Exterior

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
Bronzeville Manor walking distance to hospitals
Interior

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
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
Smart TV, computer monitors

Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront
7 Mi to Downtown: Luxe Chicago Condo
Exterior

7 Mi to Downtown: Luxe Chicago Condo

7 Mi to Downtown: Luxe Chicago Condo
Spacious two bedroom condo with a cozy feel!
Interior

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.
Fridge, microwave, oven, stovetop

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.
Lovely 2 Bedroom Condo With Pool
Exterior

Lovely 2 Bedroom Condo With Pool

Lovely 2 Bedroom Condo With Pool
Luxury Stay on UChicago Campus 11 min walk to hospitals
Exterior

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
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
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
3.6 out of 10, (12)
"The staff was polite and friendly! I didn't care that they were apparently under construction and I didn't are much for that "
The price is AED 328
AED 371 total
includes taxes & fees
25 Mar - 26 Mar
Comfort Inn Chicago Wind Creek Casino
Cozy Home Sweet Homewood.
Fridge, microwave, oven, stovetop

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (20)
"This was perfect for our needs. Great location, comfortable and clean. I'm sure we'll be back."
Cozy Home Sweet Homewood.
The Vibe Headquarters
Living area

The Vibe Headquarters

2.0 star property
9.0 out of 10, Wonderful, (2)
"Very clean and cozy! Home away from home!"
The Vibe Headquarters
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?
Condos in Highland range from to per night. These properties offer plenty of space for your whole crew at a price that’s easy on your wallet. 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?
Lock in your vacation dates and then pick from 57 condos in Highland. For business travel, a getaway with friends or anything in between, Expedia will help you find an ideal stay in a few simple clicks.
Why book your condo in Highland with Expedia?
Expedia will help you find your ideal condo in Highland. Looking for a luxury escape? Make the most of our filters to search for properties that have a 5-star rating. If you have a budget, choose how much you’d like to spend and then check out our fabulous options. We’ll help you find the right stay whatever your style of travel or plans.
How can I find cheap condos in Highland?
The best way to locate cheap condos in Highland is with Expedia’s filter tool. Refine your search results by star rating, amenities and budget to discover unbeatable prices in a few clicks.