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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Hillside vacation rentals

Apartment, Private Bathroom | Lounge

1. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, 12, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is NT$6,345
NT$10,777 total
includes taxes & fees
Oct 13 - Oct 14
At Home in Oak Park
Exterior

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, 1317, (1,317 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is NT$4,815
NT$6,580 total
includes taxes & fees
Sep 21 - Sep 22
Sentral Michigan Avenue
House (3 Bedrooms) | Interior

3. 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 NT$7,658
NT$15,026 total
includes taxes & fees
Sep 22 - Sep 23
Classic Forest Park Foursquare < 1 Mi to Blue Line
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

4. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, 7, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is NT$5,620
NT$9,947 total
includes taxes & fees
Oct 13 - Oct 14
The Oak Park Loft
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

5. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, 5, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is NT$6,920
NT$11,436 total
includes taxes & fees
Oct 14 - Oct 15
Historic Oak Park Home
Lake

6. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, 30, (30 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
The price is NT$6,171
NT$9,217 total
includes taxes & fees
Sep 20 - Sep 21
Kasa Lake Shore Chicago
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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"I think for the price, breakfast should be free. The staff and doormen were helpful."
Cheryl 1-night trip
Posted less than an hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Find out more about Hillside

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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 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.