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Browse Select Highland Park Apartments

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

9.8 out of 10, Exceptional, (125)
"My husband and I were visiting our daughter nearby for a few days. We loved our stay here. The home was clean, spacious and warm....comfortable beds and wonderful sectional for relaxing. Easy walk to wonderful restaurants. Would definitely stay again when back in Chicago. Highly recommend."
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!

Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

3.0 star property
8.4 out of 10, Very good, (14)
"The property was excellent, for my stay "
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking

Beautiful Unit CHI in Prime River North - 3

9.8 out of 10, Exceptional, (16)
"Nice place, everything as advertised. Host was very accommodating, we will definitely book again when in area. "
Beautiful Unit CHI in Prime River North - 3

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (29)
"We very much enjoyed our stay at this property! We were visiting Chicago for a fun weekend trip to celebrate our anniversary. The location was on a quiet street but within close walking distance to plenty of restaurants and shopping. The apartment was clean and very quiet in a beautiful, historic building. We highly recommend Tempo Cafe for breakfast. On our last morning in town, we actually saw Larry David, Jeff Garlin and Susie Essman at brunch there! "
Chic & Historic Apartment Steps from Mag Mile

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (14)
"This place was perfect for us, and right where we needed it to be. "
Charming Wrigleyville Home Close to the Cubs!

PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

9.4 out of 10, Exceptional, (26)
"Nice open space with large bedrooms. Quiet and clean! Perfect location to walk to local restaurants and shops "
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (128)
"Clean and great location "
Walk to Wrigley Field/Monthly Discounts Available

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (102)
"We came to town for a hockey weekend and will absolutely book with them again when we come back. Everything was exactly as pictured or described. Cozy beds, plenty of blankets, pillows, towels, etc. Quiet neighborhood on a beautiful street, and a great location to call home while commuting to and from the rinks. "
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

Lovely 4 Bedroom Spot located in Charming Old Town

10.0 out of 10, Exceptional, (23)
"The apartment was AMAZING! Even better than the photos. All the furnishings were of the finest quality, including the bed linens and towels. The mattresses were exceptionally comfortable. The kitchen was also well stocked with every type of culinary tool, plenty of glasses of every variety. We were a family of 13 and we had plenty of room. The bean bag chairs were a big hit for all ages. We loved the neighborhood. We have some members with food allergies and there were several places they...
Lovely 4 Bedroom Spot located in Charming Old Town

Regal Stylish Uptown Loft Beachfront RooftopWFHGym

8.6 out of 10, Excellent, (10)
"Although it's posted as small, it had plenty of room for us. VERY clean and comfortable, and walking distance to all that we needed. Will definitely stay here again"
The price is CA $65
CA $271 total
includes taxes & fees
Dec 30 - Dec 31
Regal Stylish Uptown Loft Beachfront RooftopWFHGym

Spirit of Evanston

9.6 out of 10, Exceptional, (5)
"Great stay. Beds were comfortable. Apartment was very clean and well appointed. "
Spirit of Evanston

Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym

9.4 out of 10, Exceptional, (14)
"we really enjoyed our stay here!! it was super nice and the bed was comfortable. there were a lot of useful amenities which we really liked. the location was convenient because it had a lot of food/bar options and was right by the music venue we went to. will definitely stay here again if we come back to chicago. thank you to the host for this little find!! "
Elegant Stylish Loft Oasis Uptown Rooftop WFH Gym

1 Garage Spot Included - Near "L" Train - Highly Rated - North Center

9.8 out of 10, Exceptional, (10)
"Our stay was phenomenal! It couldn’t have been more perfect. The apartment has everything you need. It is very clean, cozy, organized and quiet.There are tons of restaurants, shopping and things to do within waking distance. Tara was extremely accommodating and responsive. I will surely recommend this to friends and family and I will be booking again in the future. "
1 Garage Spot Included - Near "L" Train - Highly Rated - North Center

Go Out or Stay In... This Property Has Everything You Need for a Perfect Visit - Just Steps from Humboldt Park by AllSet Turnover

8.8 out of 10, Excellent, (6)
"Getting into the townhome was horrible . Code to open the gate was not working and also the key to get into the back door didn’t work. It took over an hour for someone to come let us into the unit. No Toilet paper, battery low in the firearm. Alarmed beeped all night. Sink in the basement bathroom was plugged up . "
Go Out or Stay In... This Property Has Everything You Need for a Perfect Visit - Just Steps from Humboldt Park by AllSet Turnover

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (3)
"Clean , beautiful home."
The price is CA $143
CA $370 total
includes taxes & fees
Jan 1 - Jan 2, 2025
2-bedroom apartment just 2 minutes drive to Wrigley Field

Chic apartment in phenomenal Chicago with WiFi, AC

9.4 out of 10, Exceptional, (3)
"Check in prices was a breeze, superb communication at all times and we were very pleased with our stay here"
Chic apartment in phenomenal Chicago with WiFi, AC

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (72)
"This is the 3rd time I’ve booked this Ukrainian Village apartment. It’s comfortable and has everything needed for visits into the city. "
Stay in “STYLE” Apartment, close to CHI downtown
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 Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is CA $242
CA $313 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Level Chicago – Old Town

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +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.

Frequently asked questions

What's it like to stay at an apartment in Highland Park?
You’ll find 6 apartments to choose from in Highland Park for your vacation. Why not visit the shops and take time to enjoy the gardens while you’re in this family-friendly area? Visit top places in the surrounding region such as Naval Base Great Lakes and Wrigley Field.
Why should you consider an apartment over a traditional hotel room?
Offering a kitchen for convenient meals, an apartment is often more spacious than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Highland Park?
Here are some of the favorite apartments in the area to choose from: Wrigley/Southport Corridor Garden Oasis +parking!: Situated in Chicago, 17.9 mi/28.9 km from the heart of Highland Park. Includes Smart TVs. Chic, Cozy home, by Blue Line Train Stop + Free parking: It’s situated in Chicago, 16 mi/25.7 km away. Includes free WiFi, private balconies, and Smart TVs. Stay in “STYLE” Apartment, close to CHI downtown: 20.5 mi/32.9 km away in Chicago. Amenities include Smart TVs. Chic & Historic Apartment Steps from Mag Mile: It’s situated in Chicago, 21.3 mi/34.2 km from Highland Park.
How many apartments should I expect to find in Highland Park?
Expedia has 6 apartments to book in Highland Park.
What can I expect from the weather when I travel to Highland Park?
Weather is only one factor, but it can really affect your travel plans, especially when you’re planning an extended stay in Highland Park. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Highland Park is 47 inches.
What should I see in Highland Park?
Highland Park is known for its gardens and shops. Cultural attractions include Ravinia Park and Ravinia Pavilion, whereas Chicago Botanic Garden and Lake Michigan are a couple of picturesque spots to enjoy the outdoors. Naval Base Great Lakes and Wrigley Field are other popular places to visit in the area.
What's the best way to get to and around Highland Park?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Chicago, IL (PWK-Chicago Executive), which is located 6.8 mi (10.9 km) from the heart of the city. You can also search for flights into Chicago O’Hare Intl. Airport (ORD), which is 15.1 mi (24.3 km) away. If you’d like to explore more of the area, hop aboard a train from Highland Park Station, Highland Park Ravinia Station, or Highland Park Ravinia Park Station.