Hillside Vacation Rentals from CA $84: Short-Term Rentals for 2026

Q: 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.

Q: 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.

Q: 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.

Q: 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.

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Our top choices for Hillside vacation rentals

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

1. Sentral Michigan Avenue

Downtown Chicago

Rosa

CA $209 total

includes taxes & fees

Dec 7 - Dec 8

A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Downtown Chicago

Jair

CA $332 total

includes taxes & fees

Nov 22 - Nov 23

A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

3. The Gem Museum Suites

Downtown Evanston

Zhaohua

CA $317 total

includes taxes & fees

Dec 7 - Dec 8

A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Downtown Chicago

Robert Edward

CA $314 total

includes taxes & fees

Nov 23 - Nov 24

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Lakeview

Michael

CA $244 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

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

Forest Park

CA $663 total

includes taxes & fees

Nov 24 - Nov 25

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Find vacation rentals that suit your style

Top Hillside Hotel Reviews

A lobby with a reception desk, patterned sofas, a glass-top table with a potted plant, and a decorative mirror.

Best Western Plus Chicago Hillside

Hillside

10/10 Excellent

Adetunji

A multi-story hotel with a central entrance, a flag, and a sign for Express Suites.

Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG

Hillside

10/10 Excellent

Janet

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

10/10 Excellent

Staff was very helpful answering any questions at anytime of day. Room was clean, many tv & movie channels, fridge & microwave. Bathroom was clean, with an accessable walk-in shower that dries well with door open. Hotel is about a half an hour drive from Chicago. Breakfast is a highlight of the place, eggs, sausage, breads, fruit, fresh pancakes & waffles, yogurt, juices and more! Overall a great, safe stay, would come back for sure.

Justin

A modern urban building with a distinctive curved facade, a prominent '10pin' sign, and a 'Tertius' restaurant on the ground floor.

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

10/10 Excellent

Holly

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

10/10 Excellent

Steve

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Making people feel special must be their superpower because I was pleasantly surprised by a special gift I received for my birthday. The staff was always courteous, helpful and friendly. I loved that the lobby where they had a few games you could play but was so relaxing and quiet that there were several people just sitting around and chatting. It's proximity to the L had its pros and cons. The only con being the noise but it was so minimal that you only heard it while sitting on the window...

Maegan A

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, 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 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillside vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillside vacation rentals we have selected for you start as low as CA $84 per night. Entering your travel dates in the search wizard 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.

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.

Hillside Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Hillside vacation rentals

1. Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

3. The Gem Museum Suites

4. Level Chicago – Old Town

5. Wrigleyville Suites

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

Find vacation rentals that suit your style

Top Hillside Hotel Reviews

Best Western Plus Chicago Hillside

10/10 Excellent

Find out more about Hillside

Hillside vacation rentals: An excellent choice for every season

How to find incredible deals on Hillside rentals

Frequently Asked Questions

Can I find a vacation rental in Hillside?

What are some of the best vacation rentals that Hillside has to offer?

What can I see and do in Hillside?

What are vacation rentals like in Hillside?