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Hillside Holiday Rentals

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Holiday Rentals in Hillside

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (983)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is NZ$297
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue

Cozy Gold Coast Studio Stay

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is NZ$292
includes taxes & fees
17 Nov - 18 Nov
Cozy Gold Coast Studio Stay

West Loop Living – Bright 1BR

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Thorough and easy to follow parking and check in instructions. Clean apartment. "
United States
Kira V.
The price is NZ$316
includes taxes & fees
17 Nov - 18 Nov
West Loop Living – Bright 1BR

Sleek 1BR Apt w/ Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is NZ$316
includes taxes & fees
19 Nov - 20 Nov
Sleek 1BR Apt w/ Laundry

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"Convenient location and clean place"
United States
David S.
The price is NZ$316
includes taxes & fees
17 Nov - 18 Nov
The One: A 1BR Stay That Feels Like Home

4BR Corporate Suite Central and Modern

2.0 star property
Near North Side
10.0 out of 10, Exceptional, (7)
"Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. "
United States
Phillip
The price is NZ$780
includes taxes & fees
16 Nov - 17 Nov
4BR Corporate Suite Central and Modern

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is NZ$316
includes taxes & fees
17 Nov - 18 Nov
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is NZ$316
includes taxes & fees
20 Nov - 21 Nov
Sun-Drenched 1BR Apartment

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Premium Urban 4BR - Perfect Mix of Comfort & Location

Near North Side
10.0 out of 10, Exceptional, (1)
"Nice place, clean property, great views "
United States
Zach L.
The price is NZ$798
includes taxes & fees
16 Nov - 17 Nov
Premium Urban 4BR - Perfect Mix of Comfort & Location

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (378)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town

River North Rooftop With In and Out Parking 5

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "
United States
Mike S.
The price is NZ$602
includes taxes & fees
11 Dec - 12 Dec
River North Rooftop With In and Out Parking 5

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.0 out of 10, Very good, (3)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is NZ$593
includes taxes & fees
24 Nov - 25 Nov
South Loop Rooftop With In and Out Parking 3

Complete 1BR Home Sum

Downtown Chicago
The price is NZ$316
includes taxes & fees
16 Nov - 17 Nov
Complete 1BR Home Sum

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (13)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is NZ$393
includes taxes & fees
19 Nov - 20 Nov
Twice as Nice: Chic 2BR Stay with Style & Space

Studio Unit | Chic + Prime Location

Hyde Park
10.0 out of 10, Exceptional, (1)
"Unit was convenient to our son’s home. Comfortable home. All the necessities were provided. "
United States
Michelle F.
The price is NZ$294
includes taxes & fees
26 Nov - 27 Nov
Studio Unit | Chic + Prime Location

Spacious 3-bedroom apartment near downtown, FREE PARKING

Near West Side
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is NZ$604
includes taxes & fees
19 Nov - 20 Nov
Spacious 3-bedroom apartment near downtown, FREE PARKING

Compact Studio for a Relaxed Stay

Hyde Park
The price is NZ$338
includes taxes & fees
26 Nov - 27 Nov
Compact Studio for a Relaxed Stay

Montrose Studio:Your Uptown Base

Uptown
9.8 out of 10, Exceptional, (7)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
United States
Jamie
The price is NZ$274
includes taxes & fees
1 Dec - 2 Dec
Montrose Studio:Your Uptown Base

Bright & Cozy 1BR Near UChicago

Hyde Park
10.0 out of 10, Exceptional, (2)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is NZ$316
includes taxes & fees
18 Nov - 19 Nov
Bright & Cozy 1BR Near UChicago
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

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 favorite 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 depends 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 NZ$283 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 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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This holiday home rental outside of Hillside is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.