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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (1,336 reviews)
"Great venue"
United States
Arthur Noel
$177 nightly
The price is $208
Sep 27 - Sep 28
Total with taxes and fees
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (36 reviews)
"The property was in a very nice location."
United Kingdom
Nehal Manish
$323 nightly
The price is $384
Oct 1 - Oct 2
Total with taxes and fees
Kasa Lake Shore Chicago
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

3. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (265 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
$211 nightly
The price is $241
Sep 28 - Sep 29
Total with taxes and fees
The Gem Museum Suites
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.0 out of 10, Very good, (56 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
$211 nightly
The price is $248
Sep 23 - Sep 24
Total with taxes and fees
Wrigleyville Suites
A building with a white exterior and a tree with white blossoms in front.

5. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
$364 nightly
The price is $417
Sep 23 - Sep 24
Total with taxes and fees
Historic Oak Park Residence
A modern kitchen with a large island, bar stools, and a city view.

6. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (527 reviews)
"Location and facility was very nice"
United States
Brian
$364 nightly
The price is $428
Sep 27 - Sep 28
Total with taxes and fees
Level Chicago – Old Town
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

7. 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
$316 nightly
The price is $361
Oct 14 - Oct 15
Total with taxes and fees
Historic Oak Park Home
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
$444 nightly
The price is $475
Sep 27 - Sep 28
Total with taxes and fees
Classic Forest Park Foursquare < 1 Mi to Blue Line
A living room with a sofa, armchair, dining table, and a TV.

9. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
$298 nightly
The price is $341
Oct 6 - Oct 7
Total with taxes and fees
At Home in Oak Park
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

10. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
$275 nightly
The price is $314
Oct 13 - Oct 14
Total with taxes and fees
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"We had a great time staying at the hyatt. It's in a great location and the room was super clean. The restaurants at the hotel were also really nice and my wife like the gyms scenic view. The only one point of improvement was that sometimes the fridge made a loud ticking sound which could be kind of annoying."
Geoffrey 4-night trip
Posted less than an hour ago
Hyatt Regency Chicago

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $76 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.