Hillside Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Hillside holiday rentals

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

1. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is AU$509
includes taxes & fees
16 Nov - 17 Nov
LUXE 3 BR, 2 BA + Hot Tub
A modern living room with teal sofas, a coffee table, and a TV.

2. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (27 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is AU$256
includes taxes & fees
10 Nov - 11 Nov
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A modern building with the name 'SENIORAL' prominently displayed on the facade.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,409 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is AU$217
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

4. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AU$421
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern kitchen with stainless steel appliances, a dining area with a wooden table and chairs, and a large cityscape painting on the wall.

5. Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Villa Park
8.8 out of 10, Excellent, (11 reviews)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
The price is AU$680
includes taxes & fees
10 Nov - 11 Nov
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

6. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (86 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is AU$350
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

7. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (83 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AU$395
includes taxes & fees
10 Nov - 11 Nov
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

8. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
Vibrant House, Walk to Train, Game Room
A two-story house with a brick exterior, a sloped roof, and a front porch.

9. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
The price is AU$501
includes taxes & fees
12 Nov - 13 Nov
At Home in Oak Park
A modern kitchen with a large island, bar stools, and a city view.

10. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is AU$330
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

11. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (50 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is AU$251
includes taxes & fees
10 Nov - 11 Nov
Wrigleyville Suites
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

12. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is AU$259
includes taxes & fees
16 Nov - 17 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A living room with a white sofa, a decorative vase with a plant, a small wooden figurine, and a gold decorative piece on a white coffee table.

13. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (7 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
The price is AU$627
includes taxes & fees
11 Nov - 12 Nov
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
A modern living room with a blue sofa, a patterned rug, and a television.

14. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is AU$275
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

15. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (306 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is AU$310
includes taxes & fees
16 Nov - 17 Nov
The Gem Museum Suites
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

16. Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is AU$313
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A living room with a television displaying 'NETFLIX,' a dining area with a table and chairs, and a sofa.

17. Perfect 2-bedroom apartment in lovely Berwyn for your stay

Perfect 2-bedroom apartment in lovely Berwyn for your stay
Berwyn
The price is AU$377
includes taxes & fees
15 Nov - 16 Nov
Perfect 2-bedroom apartment in lovely Berwyn for your stay
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

18. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AU$374
includes taxes & fees
11 Nov - 12 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

19. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
A rooftop terrace with a brick wall, large windows, and a metal railing.

20. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is AU$377
includes taxes & fees
10 Nov - 11 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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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Find holiday rentals that suit your style

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Top Hillside Hotel Reviews

A restaurant setting with round tables, chairs, and empty wine glasses.
Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside

Best Western Plus Chicago Hillside
Hillside

8/10 Good

We liked the breakfast. Best Western always do a good breakfast
Australia
Anonymous traveller
Reviewed June 8, 2019
Best Western Plus Chicago Hillside

Find out more about Hillside

Everything you need to know about Hillside 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 Hillside 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 Hillside holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Hillside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillside. 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 Hillside 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 Hillside holiday rentals we have selected for you start as low as AU$109 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside 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 Hillside 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 Hillside 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 Hillside. 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 Hillside?

Yes, there are holiday rentals close to the most popular sights in Hillside, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and forests in Hillside. Allow some time to check out the shops during your trip.

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

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Hillside is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Hillside?

Enjoy the area's cultural attractions such as Drury Lane Theater, or get outdoors into nature at a spot like Millennium Park. Other popular places to visit in the area include Wrigley Field and Soldier Field.

What are holiday rentals like in Hillside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillside. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.