Photo by Meghan hernandez

Highland Park Holiday Rentals

March 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday

April 2025

MondayTuesdayWednesdayThursdayFridaySaturdaySunday
  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (290)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AU$337
includes taxes & fees
13 Mar - 14 Mar
Level Chicago – Old Town

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is AU$223
includes taxes & fees
10 Mar - 11 Mar
Wrigleyville Suites

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

9.2 out of 10, Wonderful, (73)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (156)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK

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

9.4 out of 10, Exceptional, (44)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking

Experience Chicago in Hip Logan Square

9.2 out of 10, Wonderful, (5)
"Very clean townhome with all the necessary amenities. Owner was quickly responsive to all communications. Relatively quiet neighborhood. Next door neighbor had a Halloween party on a Sunday night that lasted until 3am. Wasn’t horribly loud but could hear enough noise that I needed to use my noise canceling headphones to sleep. The other nights were very quiet and peaceful. Would stay there again in the future. "
Experience Chicago in Hip Logan Square

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (24)
"The property listing was exactly as described. Very clean and quite spacious. We arrived at 530 pm and found adequate street parking. The beds were comfortable, the kitchen was stocked with key necessities and the bathrooms provided plenty of towels and basic toiletries. Our host was responsive with any concerns too. I would definitely recommend this property!"
Great 3 bedroom rental unit near Logan Square

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (168)
"My friends and I have driven down to Chicago every year now for around 4 years and we've stayed at different places each time. This place was the best one we've stayed at yet! Highly stocked and well-organized kitchen as well. Would highly recommend."
NEW LUXURY PENTHOUSE CONDO

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (16)
"Really nice location and a good place to stay. There's not a full kitchen but there is a kitchenette. We were out and about most of the time so that was no problem for us. Great neighborhood. "
Charming Wrigleyville Home Close to the Cubs!

Bright Garden Studio

8.8 out of 10, Excellent, (18)
"Place was really nice. Property manager was very kind and friendly! Responded in a timely manner. The place was nice and clean. Felt very comfortable during our stay. "
The price is AU$416
includes taxes & fees
19 Mar - 20 Mar
Bright Garden Studio

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.8 out of 10, Exceptional, (6)
"My wife and I were attending a show and stayed for a night. It's fairly close to the Aragon Ballroom and has lots of dining options nearby. The host was attentive and easy to reach. He even shoveled the snow at 11pm; as it had snowed during the show and when it was over several inches had fallen. Well done sir, cleanest walk in the neighborhood.Everything in the apartment was clean and comfortable."
The price is AU$424
includes taxes & fees
10 Mar - 11 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field

Chicago Dickens place 1 bd. Garden unit Centralized loc.

9.0 out of 10, Wonderful, (28)
"The unit was cozy and clean, and Alex was very attentive and easy to work with"
Chicago Dickens place 1 bd. Garden unit Centralized loc.

Oak Park Queen

9.4 out of 10, Exceptional, (12)
"Wonderful place. Stayed four nights and went in and out to visit family in Oak Park and nearby neighborhoods. Everything you will need when looking for a place to stay. Clean, roomy, comfy and had everything we needed!Consider staying here!"
The price is AU$410
includes taxes & fees
10 Mar - 11 Mar
Oak Park Queen

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

10.0 out of 10, Exceptional, (93)
"Great place for me to stay for work travel! Bed is cozy and Jamie does a fantastic job making guests feel welcome and comfortable. Location was super cute as well. I would definitely stay here again. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (32)
"I didn’t realize when I booked this unit that I would have to carry my luggage up two flight of stairs. Unit is spacious, bathroom is a little tight the only issue I experienced was NOISE, first two nights it was the heater (I think) the last night I could hear foot steps from above and on the early morning of Monday it sounded like construction. Location is great if you want to be steps from high end shopping and restaurants. "
Chic & Historic Apartment Steps from Mag Mile

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (63)
"The condo was well equipped including dishwasher and washing machine. Location was convenient to Fullerton bus and Metra line to Evanston. We enjoyed our stay!"
Classic Lincoln Park 2 bedroom condo- parking included

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (87)
"Spacious property. Plenty of room and great neighborhood. Wish the larger TV was upstairs. "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (57)
"We drove up from Florida for our son’s Navy graduation. After 2 days on the road, the second day mostly in the freezing ice & snow, it was wonderful to come into this cozy, warm home. I loved the details & character of this older home. The floors squeak a little & there’s some clanging as the heater turns on, but I loved those little bits. It made it feel so much more like a home rather than a hotel. The location was perfect for travel to & from Naval Station Great Lakes. There are plenty of...
The price is AU$495
includes taxes & fees
10 Mar - 11 Mar
Quaint Bungalow, near Great Lakes Naval Base

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (88)
"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."
Stunning 3 BR in prime Chicago location
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.
Don't see what you're looking for?
See all available properties in Highland Park
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Highland Park you may be interested in

Hyatt Regency O'Hare Chicago

4.0 star property
8.6 out of 10, Excellent, (1354)
"Good hotel "
The price is AU$226
includes taxes & fees
23 Mar - 24 Mar
Hyatt Regency O'Hare Chicago

Hyatt Regency Schaumburg Chicago

4.0 star property
8.4 out of 10, Very good, (1042)
"Staff was very helpful and friendly. "
The price is AU$197
includes taxes & fees
16 Mar - 17 Mar
Hyatt Regency Schaumburg Chicago

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1091)
"Beautiful hotel. Traveled with children so I didn’t like that the only fridge was filled with items for purchase and there was no microwave available for guest use"
The price is AU$252
includes taxes & fees
24 Mar - 25 Mar
Thompson Chicago, by Hyatt
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

Are there holiday rentals in Highland Park?

Yes, we give you a choice of holiday rentals where you'll be only 14.5 mi (23.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. The shops and live music are just a few reasons why travellers like Highland Park. Allow lots of time to check out the gardens and restaurants during your visit.

What are some of the best holiday rentals that Highland Park has to offer?

Great 3 bedroom rental unit near Logan Square: This holiday home rental outside of Highland Park is located on a lake, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Highland Park?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Highland Park stay.

What can I see and do in Highland Park?

Enjoy the outdoors at Lake Michigan and Chicago Botanic Garden, or simply take in cultural attractions like Ravinia Park and Ravinia Pavilion. Other popular places to visit in the area include Naval Base Great Lakes and Wrigley Field.

What are holiday rentals like in Highland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highland Park. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.