Hickory Hills Holiday Rentals

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Our top choices for Hickory Hills holiday rentals

9.8 out of 10, Exceptional, (6)
"Great two nights, nice big TV with all the stations you'll need. Big living area, comfortable bed, great kitchen to cook in if you want. Nice safe neighborhood. Highly recommend. "
United States
linda t.
The price is AU$301
includes taxes & fees
16 Dec - 17 Dec
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
9.8 out of 10, Exceptional, (34)
"Nice stay. Dog friendly. Great location. Helpful and communicative owners. Well laid out tiny home. "
United States
Laura P.
The price is AU$323
includes taxes & fees
21 Dec - 22 Dec
Less is more! Pet friendly Tiny Home near Chicago!

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (396)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is AU$232
includes taxes & fees
17 Dec - 18 Dec
Chicago luxury home suites
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AU$314
includes taxes & fees
14 Dec - 15 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Your Chicago get Away
8.4 out of 10, Very good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AU$655
includes taxes & fees
15 Dec - 16 Dec
Your Chicago get Away
2.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is AU$556
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is AU$656
includes taxes & fees
19 Dec - 20 Dec
South Loop Rooftop With In and Out Parking 3

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1005)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
The price is AU$252
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue
9.6 out of 10, Exceptional, (4)
"Had a great stay here - wonderful apartment and great location! Host was awesome and apartment was stocked super well and clean. Will absolutely stay here again! "
United States
Jackie L.
The price is AU$605
includes taxes & fees
12 Dec - 13 Dec
Modern 2BR Retreat Near Old Town & Lincoln Park

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is AU$255
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is AU$1,093
includes taxes & fees
26 Dec - 27 Dec
River North Private Deck With In and Out Parking

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (3)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
The price is AU$257
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$251
includes taxes & fees
4 Jan - 5 Jan 2026
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AU$255
includes taxes & fees
4 Jan - 5 Jan 2026
The One: A 1BR Stay That Feels Like Home
2.0 star property
The price is AU$573
includes taxes & fees
23 Dec - 24 Dec
Downtown Chicago Stay with Free In & Out Parking 5

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry
2.0 star property
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
The price is AU$634
includes taxes & fees
30 Dec - 31 Dec
Modern West Loop Gem-City Views & Prime Location 2
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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Top Hickory Hills Hotel Reviews

Find out more about Hickory Hills

Everything you need to know about Hickory Hills holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hickory Hills holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hickory Hills holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hickory Hills holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hickory Hills. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hickory Hills holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hickory Hills holiday rentals we have selected for you start as low as AU$143 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hickory Hills rentals

At Expedia, we put the best Hickory Hills holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hickory Hills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hickory Hills holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hickory Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Hickory Hills?

Yes, there are holiday rentals close to the most popular sights in Hickory Hills, or you can select a more secluded option if you're looking for a relaxing stay. Hickory Hills is known for its shopping and forests. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that Hickory Hills has to offer?

LakeHouse: This holiday home rental outside of Hickory Hills is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Hickory Hills?

Explore the area and family-friendly sights such as Childrens Museum of Oak Lawn, or get out into nature at a spot like Millennium Park. In the wider area, you’ll find popular places such as Michigan Avenue and United Center.

What’s a holiday rental in Hickory Hills like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hickory Hills. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.