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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 132 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

9.6 out of 10, Exceptional, (69)
"Nice place, not alot of parking "
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Chic Euro City Getaway- Close to Downtown

Chic Euro City Getaway- Close to Downtown

9.8 out of 10, Exceptional, (6)
"We absolutely loved the property!!! It had everything we needed and within a short drive from downtown. The host is super friendly and responsive. Overall, the best spot you will find in Chicago!!!"
Chic Euro City Getaway- Close to Downtown
3BR Prime Hyde Park Location Near University of Chicago and Dining
Living area

3BR Prime Hyde Park Location Near University of Chicago and Dining

2.0 star property
10.0 out of 10, Exceptional, (2)
"Stayed for two nights with a few college friends. We’re able to find street parking pretty easily but the parking is full all up and down. Apartment is on third floor, so need to be able to carry luggage up and down. Space was clean and we enjoyed hanging out in the dining and living room. Beds were huge and so comfy! Just be careful taking garbage out the back stairs, as steps were slippery from rain. "
3BR Prime Hyde Park Location Near University of Chicago and Dining
Charming 3BR Chicago Apt in Prime Location
Living area

Charming 3BR Chicago Apt in Prime Location

9.4 out of 10, Exceptional, (8)
"The location is great if you are attending an event at the UChicago. The apartment is big and bright. A couple of small issues - the paint in the shower (the tiles were painted over!) is peeling and falling off while you shower and the cleaning needs to be a little more thorough with the floor boards. The biggest problem was the heat. It is a radiator system. I am sure it works great when the building people actually turn it on, but it was not on when we were there. It was 39 degrees outside,...
Charming 3BR Chicago Apt in Prime Location
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
Living area

Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago

6.0 out of 10, (2)
"Very nice place! So much space. Quiet neighborhood. "
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
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!
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
The Vibe Headquarters
Interior

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
Walk to Metra: Pet-friendly Blue Island Apt
Living area

Walk to Metra: Pet-friendly Blue Island Apt

3.0 star property
10.0 out of 10, Exceptional, (1)
"I like everything about that place will remind it to friends"
Walk to Metra: Pet-friendly Blue Island 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

9.2 out of 10, Wonderful, (9)
"The aesthetic was very welcoming and the vibe was perfect. The house description is very accurate, clean and cozy. Thank you! "
Private Romantic 2 Bedroom suite in the beautiful and historic Beverly community
Spacious 3-bedroom apartment in awesome Chicago with AC, WiFi
Living area

Spacious 3-bedroom apartment in awesome Chicago with AC, WiFi

2.0 star property
Spacious 3-bedroom apartment in awesome Chicago with AC, WiFi
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
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Living area

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!
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
Room

Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community

9.0 out of 10, Wonderful, (14)
"it was nice "
Lovely cozy 2 Bedroom Private Suite In Historical Beverly Community
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!

8.0 out of 10, Very Good, (8)
"this property was just stunning , i couldn't have asked for a better home for thanksgiving . "
Dyer Family Escape - 20 Mi to Lake Michigan!
Remodeled Chicago Apartment < 9 Mi to Downtown
Chicago Vacation Rental | 4BR | 2BA | 1,850 Sq Ft | Stairs Required

Remodeled Chicago Apartment < 9 Mi to Downtown

9.6 out of 10, Exceptional, (4)
"Our family had a nice time and enjoyed our stay."
Remodeled Chicago Apartment < 9 Mi to Downtown
Penthouse, Lux stay near Downtown, McComick & Lake
9ecaf173 9603 42d1 a8b4 09c36b108ea4

Penthouse, Lux stay near Downtown, McComick & Lake

10.0 out of 10, Exceptional, (12)
"This was a beautiful home. It was clean and comfortable. So easy to access the property. Great neighborhood on the south side, close to great food spots and downtown. "
Penthouse, Lux stay near Downtown, McComick & Lake
Gorgeous 4BDR in Chicago / 15mins from DWTN Brand New!
Living area

Gorgeous 4BDR in Chicago / 15mins from DWTN Brand New!

2.0 star property
10.0 out of 10, Exceptional, (2)
"10/10 very clean very nice looks just like the pictures "
Gorgeous 4BDR in Chicago / 15mins from DWTN Brand New!
Cozy 1 Bed room apartment, all to yourself!
Living area

Cozy 1 Bed room apartment, all to yourself!

Cozy 1 Bed room apartment, all to yourself!
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
25 Mar - 26 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

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 search for accommodations in the area with similar amenities to an apartment. 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. Even filter by similar property types like vacation homes, condos, or cabins. Favorite sights to explore include Indiana Dunes National Park.
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: Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum: Situated in Chicago, 19.7 mi/31.8 km from the heart of Highland. Includes free WiFi, sofa beds, and Smart TVs. Charming 3BR Chicago Apt in Prime Location: Located 18.3 mi/29.4 km away in Chicago. Free WiFi and Smart TVs are included. Access to a hot tub is available on site. The Vibe Headquarters: It’s located in Chicago, 18 mi/29 km away. Chic 3-bedroom apartment with WiFi, AC in welcoming Chicago: It’s situated in Chicago, 17.1 mi/27.6 km from Highland.
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.