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Compare 115 Apartments in Highland with updated reviews, rates, and availability.

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
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
Charming 3BR Chicago Apt in Prime Location
Living area
Charming 3BR Chicago Apt in Prime Location
9.6 out of 10, Exceptional, (7)
"This apartment is in a quiet, safe building in very walkable Hyde Park.. Lots of space & comfy beds. Owner is very responsive."
Charming 3BR Chicago Apt in Prime Location
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Historic Greystone just South of University of Chicago Hyde Park Campus
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
2.0 star property
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Chicago Apartment: 4 Mi to Lake Michigan!
Chicago Vacation Rental | 4BR | 1BA | 2,000 Sq Ft | Stairs Required
Chicago Apartment: 4 Mi to Lake Michigan!
10.0 out of 10, Exceptional, (2)
"The manager was very nice and accommodating "
Chicago Apartment: 4 Mi to Lake Michigan!
Woodlawn ~ Entire Luxury Apt
Living area
Woodlawn ~ Entire Luxury Apt
Woodlawn ~ Entire Luxury Apt
Private Romantic 2 Bedroom suite in the beautiful and historic Beverly community
Living area
Private Romantic 2 Bedroom suite in the beautiful and historic Beverly community
9.6 out of 10, Exceptional, (7)
"The apartment was clean and welcoming! The location is perfect! We were right across from a meta stop and bus stop! A quick 30 min ride on either and you are right downtown! We go to to riot fest every year and plan on making this our stay next year to! "
Private Romantic 2 Bedroom suite in the beautiful and historic Beverly community
Portage Studio: 11 Miles to Indiana Dunes!
Portage Vacation Rental | Studio | 1BA | Stairs Required | 400 Sq Ft
Portage Studio: 11 Miles to Indiana Dunes!
Portage Studio: 11 Miles to Indiana Dunes!
Modern "Blast From The Past" A Real Retreat 3Bedroom Unit
Interior
Modern "Blast From The Past" A Real Retreat 3Bedroom Unit
9.6 out of 10, Exceptional, (5)
"Very nice and modern place. Great communication from the owner, overall a great experience. "
Modern "Blast From The Past" A Real Retreat 3Bedroom Unit
Plant MOOD2! FREE STREET PARKING & Wi-Fi!
Living area
Plant MOOD2! FREE STREET PARKING & Wi-Fi!
10.0 out of 10, Exceptional, (1)
"I was having trouble getting in on a sunday and they helped me thru it with "
Plant MOOD2! FREE STREET PARKING & Wi-Fi!
The Vibe Headquarters
Interior
The Vibe Headquarters
2.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean and cozy! Home away from home!"
The Vibe Headquarters
Spacious 3-Bedroom Haven Near Chicago's Top Attractions
Exterior
Spacious 3-Bedroom Haven Near Chicago's Top Attractions
2.0 star property
6.0 out of 10, (1)
"Needs a new toilet"
Spacious 3-Bedroom Haven Near Chicago's Top Attractions
LONG STAY,4BED,UC 2MI,FREE PRKG,DWTN 15MIN
Interior
LONG STAY,4BED,UC 2MI,FREE PRKG,DWTN 15MIN
9.4 out of 10, Exceptional, (6)
"Was concerned about the neighborhood. Was pleasantly surprised that I was concerned for no reason at all. Nice four-bedroom apartment. Would recommend."
LONG STAY,4BED,UC 2MI,FREE PRKG,DWTN 15MIN
Blue Island Apartment: Walk to Metra!
Living area
Blue Island Apartment: Walk to Metra!
3.0 star property
10.0 out of 10, Exceptional, (1)
"I like everything about that place will remind it to friends"
Blue Island Apartment: Walk to Metra!
Bronzeville Luxury- 2Bd 1ba! ONLY 10 MINS from downtown!
Interior
Bronzeville Luxury- 2Bd 1ba! ONLY 10 MINS from downtown!
Bronzeville Luxury- 2Bd 1ba! ONLY 10 MINS from downtown!
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
The "Pool Barn" offers plenty to do inside, outside, and in the area.
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
9.0 out of 10, Wonderful, (14)
"We loved it. We had our five grandkids with us and they were entertained the entire time we were there. We all enjoyed the pool, hot tub and the game room. It's a short drive to Indiana dunes. Would highly recommend this place. Hoping to return next year. Kim and Don were great hosts."
The price is AED 621
AED 786 total
includes taxes & fees
10 Nov - 11 Nov
The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Your Home Away from home -12 mins from Downtown
Dining
Your Home Away from home -12 mins from Downtown
10.0 out of 10, Exceptional, (1)
"This property was exactly as listed. No complaints."
Your Home Away from home -12 mins from Downtown
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Private kitchen
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.0 out of 10, Very Good, (8)
"Place was clean & smelled good. Easy parking out front & getting in & felt safe. We had 5 adults, wish the beds were actually Queen not full/queen. A few discrepancies in listing but over-all good"
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
3 bedroom apartment easily 15 mins from downtown 10 mins from Chicago’s beach!
Exterior
3 bedroom apartment easily 15 mins from downtown 10 mins from Chicago’s beach!
9.0 out of 10, Wonderful, (2)
"Really beautiful property in historic south side, lots of space and comfortable with full kitchen and full bath. Owner was very easy to communicate with and answered messages immediately. the downstairs unit is quite loud since you can hear every footstep in the upstairs unit but other than that the neighborhood is very quiet, neighbors all waved and were friendly."
3 bedroom apartment easily 15 mins from downtown 10 mins from Chicago’s beach!
Dyer Family Escape - 20 Mi to Lake Michigan!
Dyer Vacation Rental | 5BR | 3BA | 4,920 Sq Ft | Steps Required
Dyer Family Escape - 20 Mi to Lake Michigan!
7.8 out of 10, Good, (7)
"The home is beautiful with a warm welcoming feeling. Each bedroom has its own charm. The back deck view of the lake is exquisite. Every imaginable kitchen extra was there, spices, teas, coffees. The code checkin was a breeze. We were able to get our working time in and still enjoy the space. We made an excellent choice."
Dyer Family Escape - 20 Mi to Lake Michigan!
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

What's it like to stay at an apartment in Highland?
There might not be many choices within the heart of Highland, but Expedia can help you locate accommodations within the larger area similar to apartments. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also filter by similar property types like vacation homes, condos, or guest houses.
How do you know if an apartment is a good option for you?
An apartment features a kitchen for convenient meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, but also for families wanting the conveniences of home.
What's the top apartment for a stay in Highland?
Listed below are some of the more popular apartments in the area: Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community: Situated in Chicago, 14.8 mi/23.8 km from the heart of Highland. Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum: Located 19.7 mi/31.8 km away in Chicago. Free WiFi, sofa beds, and Smart TVs are included. Woodlawn ~ Entire Luxury Apt: 17.9 mi/28.8 km away in Chicago.
What can I expect from the weather during my trip to Highland?
Weather is only one factor, but it can really affect your travel plans, especially if you’re planning an extended stay in Highland. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Highland is 48 inches.
What should I see in Highland?
Indiana Dunes National Park and Hoosier Prairie are a couple of lovely local spots to get outside and enjoy nature. Purdue University Northwest and Hard Rock Casino Northern Indiana are a couple of places you’ll find in the larger area.
What's the best way to get to and around Highland?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Chicago Midway Airport (MDW), which is located 22 mi (35.5 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O’Hare Intl. Airport (ORD), which is 37.4 mi (60.2 km) away. If you’d like to explore around the area, you may want a rental car for your journey.