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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Hillside holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,070 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ฿3,457
฿4,984 total
includes taxes & fees
9 Feb - 10 Feb
Sentral Michigan Avenue
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (422 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
The price is ฿6,095
฿7,932 total
includes taxes & fees
9 Feb - 10 Feb
Level Chicago – Old Town
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is ฿3,745
฿4,397 total
includes taxes & fees
9 Feb - 10 Feb
Wrigleyville Suites
Apartment, Private Bathroom | Lounge

At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
United States
Kathryn
The price is ฿4,010
฿8,092 total
includes taxes & fees
9 Feb - 10 Feb
At Home in Oak Park
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (104 reviews)
"This is a fantastic hotel with super friendly staff"
United States
German
The price is ฿5,732
฿6,562 total
includes taxes & fees
10 Feb - 11 Feb
The Gem Museum Suites
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "
United States
judith
The price is ฿3,783
฿7,832 total
includes taxes & fees
9 Feb - 10 Feb
Historic Oak Park Home
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (690 reviews)
"Perfect location and very clean! "
United States
Latoya
Kasa Magnificent Mile Chicago
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely awesome "
United States
Erik
The price is ฿3,783
฿7,832 total
includes taxes & fees
10 Feb - 11 Feb
Historic Oak Park Residence
Design Apartment, Private Bathroom (The Oak Park Loft) | 2 bedrooms

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is ฿3,524
฿7,535 total
includes taxes & fees
9 Feb - 10 Feb
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

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent
"Great room, very quiet and staff was friendly and accomodating."
Samuel 1-night trip
Posted 2 days ago
Courtyard by Marriott Chicago Magnificent Mile

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 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 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 Michigan Avenue.

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.