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Hillside Holiday Rentals

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Check prices for these dates

Tonight
18 Nov - 19 Nov
Tomorrow
19 Nov - 20 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Hillside

Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"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 HK$482
HK$1,223 total
includes taxes & fees
19 Nov - 20 Nov
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

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 HK$428
HK$1,237 total
includes taxes & fees
2 Dec - 3 Dec
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

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 HK$428
HK$1,237 total
includes taxes & fees
3 Dec - 4 Dec
The One: A 1BR Stay That Feels Like Home
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (986)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is HK$783
HK$1,148 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Downtown Chicago
The price is HK$428
HK$1,237 total
includes taxes & fees
2 Dec - 3 Dec
Complete 1BR Home Sum
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

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 HK$428
HK$1,237 total
includes taxes & fees
2 Dec - 3 Dec
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

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 HK$428
HK$1,237 total
includes taxes & fees
2 Dec - 3 Dec
Sun-Drenched 1BR Apartment
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (383)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
4 bedrooms, iron/ironing board, travel cot, WiFi
Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5

2.0 star property
Downtown Chicago
The price is HK$1,166
HK$1,545 total
includes taxes & fees
24 Nov - 25 Nov
Modern West Loop Gem-City Views & Prime Location 5
Fridge, microwave, oven, stovetop
South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3

Downtown Chicago
8.6 out of 10, Excellent, (4)
"Modern and stylish apartment in a great location. Lots of extra thoughtful touches made it a great stay. "
Australia
Angela M.
The price is HK$902
HK$2,577 total
includes taxes & fees
24 Nov - 25 Nov
South Loop Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5

Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is HK$956
HK$2,611 total
includes taxes & fees
11 Dec - 12 Dec
River North Rooftop With In and Out Parking 5
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is HK$2,133
HK$2,503 total
includes taxes & fees
19 Nov - 20 Nov
Chicago luxury home suites
TV, offices
Bright & Cozy 1BR Near UChicago

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 HK$428
HK$1,237 total
includes taxes & fees
2 Dec - 3 Dec
Bright & Cozy 1BR Near UChicago
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

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 HK$428
HK$1,237 total
includes taxes & fees
2 Dec - 3 Dec
Sleek 1BR Apt w/ Laundry
Interior
Your Chicago get Away

Your Chicago get Away

Downtown Chicago
8.4 out of 10, Very good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is HK$2,025
HK$3,917 total
includes taxes & fees
24 Nov - 25 Nov
Your Chicago get Away
Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (9)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$466
HK$1,205 total
includes taxes & fees
2 Dec - 3 Dec
Modern Studio Near UChicago
Fridge, microwave, oven, stovetop
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Little Village
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is HK$529
HK$1,647 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

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

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is HK$482
HK$1,427 total
includes taxes & fees
2 Dec - 3 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
Private kitchen
Spacious 3-bedroom apartment near downtown, FREE PARKING

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 HK$451
HK$2,580 total
includes taxes & fees
19 Nov - 20 Nov
Spacious 3-bedroom apartment near downtown, FREE PARKING
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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Clean room, spacious, free breakfast was a huge perk! "
Ashley 3-night trip
Posted 4 days ago
The Whitehall Hotel, BW Premier Collection

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 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.