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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 790 Apartments in Highland Park with updated reviews, rates, and availability.

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
3 bedrooms, WiFi, bed sheets

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

9.2 out of 10, Wonderful, (74)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

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

9.4 out of 10, Exceptional, (46)
"This property is very clean and very cozy. The location is great, except at night, I was able to hear the train and highway traffic. My husband wasn't bothered at all. We still liked it and suited our needs. The amenities were excellent. There's plenty of parking. "
Chic, Cozy home, by Blue Line Train Stop + Free parking
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (8)
"The property is very quiet, clean, well appointed, and is in a great location. It’s only a 3 minute walk to the Brown Line which easily gets you downtown in half an hour and not worry about parking. I did notice the absence of a microwave which would have been an added convenience. Overall, it suited my needs perfectly and will consider it again if I get back to Chicago."
The price is AED 312
AED 887 total
includes taxes & fees
3 Apr - 4 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field
Charming Wrigleyville Home Close to the Cubs!
Interior

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (17)
"Great neighborhood. Free and easy parking. "
Charming Wrigleyville Home Close to the Cubs!
Walk to Wrigley Field/Monthly Discounts Available
Fridge, microwave, oven, stovetop

Walk to Wrigley Field/Monthly Discounts Available

9.6 out of 10, Exceptional, (135)
"The location was amazing! Right on Clark Street a quick walk to Wrigley field and all of the nearby nightlife. Came for Saint Patrick's Day weekend and couldn't have picked a better location, ease of access to the city through the red and brown lines was great. The unit was spacious and clean. When I return to Chicago I will definitely stay here again if the unit is available. "
Walk to Wrigley Field/Monthly Discounts Available
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (33)
"What an exceptional property! Perfect for a two-person getaway. It's right around the corner from shops and restaurants in the terrific Gold Coast neighborhood. Beautiful, modern decor with vintage building charm. It is very safe, quiet and comfortable - we got great sleep here. The host was communicative and everything was very easy. Definitely plan to come back to this gem!"
Chic & Historic Apartment Steps from Mag Mile
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Smart TV, DVD player, books, stereo

Stylish, Inviting 2-BR near Logan Square and Wrigley Field

10.0 out of 10, Exceptional, (46)
"Property was easy to access. Great place to relax and enjoy some peace. Loved the decor! Hosts were super friendly and it was easy to communicate with them. Fenced yard for our dogs was great! "
Stylish, Inviting 2-BR near Logan Square and Wrigley Field
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
Fridge, microwave, oven, stovetop

Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94

10.0 out of 10, Exceptional, (3)
"This is the perfect place for a couple to stay for a weekend in the Windy City! It has everything you need, and youre close to the big attractions! Parking can be a little tricky, but the fact that its free helps a lot! Toby is a wonderful host. You'll feel taken care of, and enjoy your time at this property!"
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Smart TV, fireplace, DVD player, books

The Logan Square Guest House - Classic Vintage Comfort With Free Parking!

10.0 out of 10, Exceptional, (23)
"This was the perfect place to stay for a four day visit to Chicago. The host was super responsive and the apartment is stunning with beautiful original artwork and every convenience you could possibly need. As a frequent Chicago visitor I will definitely rent this space again!"
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Terrace/patio

Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!

9.8 out of 10, Exceptional, (16)
"We stayed here for just over a week for our daughter's wedding. The VRBO was clean, comfortable and very convenient to the things we were doing. Judy, the host, was easy to communicate with. Highly recommend."
Book Spring & Summer Trip, Safe & Serene, Beautiful Unit Chicago - SuperHost!
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Property grounds

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover

8.6 out of 10, Excellent, (7)
"This lovely apartment was a great location for our family. Close to shops and restaurants. Easy walk to the Red Line train. The place was well stocked with bedding and the mattresses were quite comfy. We enjoyed cooking and hanging out in the living area. "
Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by AllSet Turnover
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is AED 195
AED 755 total
includes taxes & fees
8 Apr - 9 Apr
Bright Garden Studio
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Pool

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (95)
"We had an amazing stay at Jamie’s place. Quiet location, great host, and lovely accommodations. If you’re visiting Chicago, highly recommend staying at Jamie’s. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!
Smart TV, fireplace, DVD player, foosball

Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!

10.0 out of 10, Exceptional, (87)
"Property and location were great! Very responsive to questions and check in and out were easy."
Soaring, Dramatic, & Spacious Wrigley Loft with Rooftop, Fireplace, BBQ Grill!
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Fridge, microwave, oven, stovetop

Perfect 4 Bedroom/3 Bath in the HEART of Old Town

10.0 out of 10, Exceptional, (55)
"This unit served our family of five well for a few days get away in the city. The hot water went out while we were there but the owner communicated and responded timely. It was a bit dusty, as if it hadn't been occupied in some time, but otherwise it was fine. Can't beat the location and Old Town is awesome."
Perfect 4 Bedroom/3 Bath in the HEART of Old Town
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Fridge, microwave, oven, stovetop

Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square

3.0 star property
10.0 out of 10, Exceptional, (8)
"Really cute place and great location. Love the included parking space. It was just the two of us, but the place is huge and could easily sleep many. The biggest issue was the plumbing - we only had one working sink and one working shower, and they were on different floors. But we weren’t around except to sleep, so it worked out."
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Beautiful apartment in peaceful Elk Grove
Lobby

Beautiful apartment in peaceful Elk Grove

Beautiful apartment in peaceful Elk Grove
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Beach

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

10.0 out of 10, Exceptional, (216)
"Our group consisted of two couples and this place was perfect for us. Very comfortable, kitchen is well equipped with everything you could need. "
Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
Great Location-Beautiful Friendly Andersonville Neighborhood
Smart TV, books

Great Location-Beautiful Friendly Andersonville Neighborhood

10.0 out of 10, Exceptional, (177)
"Beautifully appointed apartment in the perfect location for all Andersonville has to offer."
Great Location-Beautiful Friendly Andersonville Neighborhood
Vibrant 3BR Flamingo Paradise | Heart of Lakeview!
Fridge, microwave, oven, stovetop

Vibrant 3BR Flamingo Paradise | Heart of Lakeview!

Vibrant 3BR Flamingo Paradise | Heart of Lakeview!
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
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (297)
"Spacious, clean rooms! Large windows make for a fabulous view!"
The price is AED 705
AED 909 total
includes taxes & fees
6 Apr - 7 Apr
Level Chicago – Old Town
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very good place at a very good price! Communication is the only need for improvement in my opinion. "
The price is AED 518
AED 792 total
includes taxes & fees
3 Apr - 4 Apr
Wrigleyville Suites
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is AED 195
AED 755 total
includes taxes & fees
8 Apr - 9 Apr
Bright Garden Studio
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? Favorite sights to visit while in town include Lake Michigan.
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?
Below are some of the top apartments in the area to choose from: 2-bedroom apartment just 2 minutes drive to Wrigley Field: Situated in Chicago, 16.9 mi/27.1 km from the heart of Highland Park. Includes free WiFi and Smart TVs. Chic, Cozy home, by Blue Line Train Stop + Free parking: Located 16 mi/25.7 km away in Chicago. Free WiFi, private balconies, and Smart TVs are included. Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!: It’s situated in Chicago, 18 mi/29 km away. Includes Smart TVs. Bright Garden Studio: 11.7 mi/18.8 km away in Evanston. Private patios, fireplaces, and separate dining areas are included.
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 Lake Michigan and Chicago Botanic Garden 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.