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Hillside Holiday Rentals

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Holiday Rentals in Hillside

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (906)
"great food spots all around and beautiful sites to see "
The price is AU$348
includes taxes & fees
22 Sept - 23 Sept
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (493)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (348)
"A lot of good food options walkable distance. "
The price is AU$580
includes taxes & fees
22 Sept - 23 Sept
Level Chicago – Old Town

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (645)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is AU$304
includes taxes & fees
5 Oct - 6 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (356)
"Great stay!"
The price is AU$304
includes taxes & fees
5 Oct - 6 Oct
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (194)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (210)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is AU$349
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (337)
"Easy parking. Close to El. Nice condo."
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is AU$304
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North

The Gem Museum Suites

3.5 star property
9.6 out of 10, Exceptional, (87)
"Super nice hotel and staff "
The price is AU$346
includes taxes & fees
30 Sept - 1 Oct
The Gem Museum Suites

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (167)
"This place has everything for a multi-night stay."
Kasa River North Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is AU$349
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (18)
"Excellent location and very clean! Would stay again!"
The price is AU$311
includes taxes & fees
7 Sept - 8 Sept
Wrigleyville Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (135)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$265
includes taxes & fees
23 Sept - 24 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is AU$1,896
includes taxes & fees
8 Sept - 9 Sept
Art Villa

Clean & Equipped 1BR Apt

8.8 out of 10, Excellent, (18)
"Good experience. Would stay there again "
The price is AU$313
includes taxes & fees
8 Sept - 9 Sept
Clean & Equipped 1BR Apt

Charming 2BR in Vibrant Lakeview

9.2 out of 10, Wonderful, (14)
The price is AU$339
includes taxes & fees
10 Sept - 11 Sept
Charming 2BR in Vibrant Lakeview

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (18)
"Great place! 15 min walk to Wrigley "
The price is AU$304
includes taxes & fees
1 Oct - 2 Oct
Cozy, Fully Set-Up 1BR Space

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is AU$297
includes taxes & fees
10 Sept - 11 Sept
Cozy Studio in Hyde Park-Walk to Lake & University

Uptown Studio Gem Sum

7.0 out of 10, Good, (4)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
The price is AU$274
includes taxes & fees
1 Oct - 2 Oct
Uptown Studio Gem Sum
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

Find out more about 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$265 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?

Amazing 3-bedroom house with WiFi and AC in awesome Chicago: This holiday home rental outside of Hillside has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.