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Search Condos Rentals in Highland from CA $217

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Highland Condo Rentals

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

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

8.0 out of 10, Very good, (1)
"Stayed here with my spouse, son, father and his partner to visit my brother who lives in Chicago. We wanted someplace close to Shed Aquarium. This location checked that box (shed was about 17 minutes from this spot)! The co-host was friendly and responsive when we had some issues with finding the correct entrance. Area is decent, lots of sirens and near the L train but you can mostly only hear that when you are outside on the back deck (also I feel like this is normal Chicago noise). My son...
Tranquil 2-bedroom condo in charming Chicago with WiFi, AC
♛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, (16)
"Loved our stay! The property was beautiful, with comfortable furnishings that made us feel right at home. Everything was clean and well-maintained. We’ll definitely rent again!"
♛The Broadway Special♛ - 2 Bd/1 Bath Smart-Condo!
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, (18)
"Perfect for what we needed"
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Gorgeous N. Kenwood/Hyde Park
Fridge, microwave, oven, stovetop

Gorgeous N. Kenwood/Hyde Park

2.0 star property
10.0 out of 10, Exceptional, (2)
"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
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)
"Wonderful place! "
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)
"Apartment is simple but clean. Beds are very comfortable and there is plenty of space for up to 8 with 2 bedrooms that have trundle beds. Not a great kitchen for cooking as the cooking supplies are very minimal (more minimal than a typical Vrbo). Smells of smoke although lots of air purifiers have certainly helped with this."
The price is CA $217
CA $567 total
includes taxes & fees
May 5 - May 6
Comfortable Condo in the Heart of Bronzeville by RedAwning
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!
7 Mi to Downtown: Luxe Chicago Condo
Exterior

7 Mi to Downtown: Luxe Chicago Condo

8.0 out of 10, Very good, (1)
"Nice"
7 Mi to Downtown: Luxe Chicago Condo
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)
"Awesome place"
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)
"The accommodations were exceptionally attractive. It is impressive at first sight. Would highly recommend to friends and family"
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

7.4 out of 10, Good, (6)
"Overall a nice stay. The property was as advertised and a short cab/uber to McCormick Place. A few minor issues which have all be detailed in other reviews but overall worth the price for a downtown location."
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
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
Bronzeville Manor walking distance to hospitals
Interior

Bronzeville Manor walking distance to hospitals

9.6 out of 10, Exceptional, (15)
"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
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.
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!
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, (3)
"Our family stay was wonderful! The property was great, the owners were available and courteous. "
Luxury Stay on UChicago Campus 11 min walk to hospitals
A luxury vintage condo close to lakefront and minutes from downtown!
Fridge, microwave, oven, stovetop

A luxury vintage condo close to lakefront and minutes from downtown!

A luxury vintage condo close to lakefront and minutes from downtown!
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
Microwave, oven, stovetop, dishwasher

Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.

10.0 out of 10, Exceptional, (1)
"Beautiful, comfortable apartment. Loved the decor. Stairs up to building’s entry and then down to the basement apartment present a daunting challenge, particularly when carrying luggage. "
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
Oak Lawn big 2nd floor Condo for 8 ppl 3 bedroom 2 bath Sofa bed Garage Parking.
Fridge, microwave, oven, stovetop

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
Comfort Double Room

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.0 out of 10, (22)
"Nice inside room but it’s not safe outside area"
The price is CA $124
CA $141 total
includes taxes & fees
May 1 - May 2
Comfort Inn Chicago Wind Creek Casino
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Exterior

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

7.8 out of 10, Good, (7)
"Overall it was a great experience and I’ll be coming back sooner"
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Terrace/patio

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.2 out of 10, Very good, (34)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, 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?
Condos in Highland range from CA $217 to CA $217 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 55 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.