A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Hillside vacation 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 traveler
$348 nightly
The price is $372
Oct 26 - Oct 27
Total with taxes and fees
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, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
$150 nightly
The price is $160
Oct 20 - Oct 21
Total with taxes and fees
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

3. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
$460 nightly
The price is $492
Oct 20 - Oct 21
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
$283 nightly
The price is $302
Oct 19 - Oct 20
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (71 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
$208 nightly
The price is $238
Nov 2 - Nov 3
Total with taxes and fees
Kasa Lake Shore Chicago
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
$259 nightly
The price is $297
Oct 26 - Oct 27
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern building with the name 'SENIORAL' prominently displayed on the facade.

7. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,375 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
$143 nightly
The price is $168
Nov 9 - Nov 10
Total with taxes and fees
Sentral Michigan Avenue
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

8. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (289 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
$188 nightly
The price is $215
Nov 17 - Nov 18
Total with taxes and fees
The Gem Museum Suites
Terrace/patio

9. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"The apartment was clean and had everything we needed for a comfortable stay. Highly recommended!"
Italy
Marco
$310 nightly
The price is $355
Oct 25 - Oct 26
Total with taxes and fees
At Home in Oak Park
A modern kitchen with stainless steel appliances, a dining area with a wooden table and chairs, and a large cityscape painting on the wall.

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

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Villa Park
8.6 out of 10, Excellent, (10 reviews)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
$478 nightly
The price is $507
Oct 26 - Oct 27
Total with taxes and fees
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
$206 nightly
The price is $236
Oct 26 - Oct 27
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking
Miscellaneous

12. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
$224 nightly
The price is $256
Oct 27 - Oct 28
Total with taxes and fees
1BR Apartment - Walk to Shops - Downtown OAK PARK
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

13. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
$276 nightly
The price is $316
Oct 27 - Oct 28
Total with taxes and fees
Historic Oak Park Home
A modern kitchen with a large island, bar stools, and a city view.

14. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
$309 nightly
The price is $363
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

15. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveler
$71 nightly
The price is $78
Oct 30 - Oct 31
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
A glass elevator with a city view.

16. Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
$255 nightly
The price is $292
Oct 27 - Oct 28
Total with taxes and fees
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

17. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
United States
Bridget
$205 nightly
The price is $211
Nov 2 - Nov 3
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
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
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
$254 nightly
The price is $269
Nov 9 - Nov 10
Total with taxes and fees
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
$294 nightly
The price is $337
Oct 27 - Oct 28
Total with taxes and fees
The Oak Park Loft
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

20. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
$243 nightly
The price is $287
Nov 2 - Nov 3
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
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 Hillside Hotel Reviews

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

10/10 Excellent
"Everything was nice in the room. Staff was very accommodating. We had a package mailed to this hotel overnight due to my forgetfulness and Hilton did an amazing job at getting it to me on time. Thanks to everyone."
Edward 1-night trip
Posted 6 hours ago
Hilton Chicago O'Hare Airport

Find out more about Hillside

Everything you need to know about Hillside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillside vacation 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 low season months. For more hustle and bustle, you may prefer to visit Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $82 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hillside rentals

At Expedia, we put the best Hillside vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Hillside?

Yes, you can find vacation rentals near popular sights in Hillside, or you can choose a secluded option if you're looking for relaxation. 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 vacation rentals that Hillside has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Hillside is located in the city center and has a balcony, a barbecue grill, 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 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 vacation rentals like in Hillside?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Hillside. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.