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 modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥22,637
￥26,572 total
includes taxes & fees
Nov 9 - Nov 10
Sentral Michigan Avenue
A modern bathroom with a vanity, mirror, shower, and bathtub.

2. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (287 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ￥36,358
￥41,623 total
includes taxes & fees
Nov 12 - Nov 13
The Gem Museum Suites
Terrace/patio

3. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ￥33,666
￥56,094 total
includes taxes & fees
Oct 26 - Oct 27
At Home in Oak Park
A modern kitchen with a large island, bar stools, and a city view.

4. 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
The price is ￥42,109
￥53,333 total
includes taxes & fees
Nov 9 - Nov 10
Level Chicago – Old Town
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ￥28,296
￥43,039 total
includes taxes & fees
Nov 2 - Nov 3
Kasa Lake Shore Chicago
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

6. 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
The price is ￥28,312
￥49,964 total
includes taxes & fees
Oct 27 - Oct 28
Historic Oak Park Home
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

7. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (64 reviews)
"terrible experience i need my money back, I cant check in at all please give me back my money"
United States
Jainul
The price is ￥25,223
￥29,609 total
includes taxes & fees
Nov 3 - Nov 4
Wrigleyville Suites
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is ￥38,255
￥75,061 total
includes taxes & fees
Oct 18 - Oct 19
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

9. 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 price is ￥28,042
￥49,656 total
includes taxes & fees
Oct 27 - Oct 28
The Oak Park Loft
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"Room was good … but there was really bad sewer smell in bathroom"
Gurpreet 3-night trip
Posted 7 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Hillside

Search for holiday rentals in Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillside using one of the methods below:

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Look no further and take a look at our great range of rental properties in Hillside!

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.