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Hillside Holiday Rentals

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Our top choices for Hillside holiday rentals

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is HK$752
HK$883 total
includes taxes & fees
8 Jan - 9 Jan
Chicago luxury home suites

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1034)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is HK$854
HK$1,231 total
includes taxes & fees
7 Jan - 8 Jan
Sentral Michigan Avenue

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"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$537
HK$1,289 total
includes taxes & fees
11 Jan - 12 Jan
Gold Coast Living: Modern Studio Unit

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$490
HK$1,312 total
includes taxes & fees
15 Jan - 16 Jan
1BR Modern Luxe Apt with In-Unit Laundry

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$491
HK$1,313 total
includes taxes & fees
7 Jan - 8 Jan
Sleek 1BR Apt w/ Laundry

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$490
HK$1,312 total
includes taxes & fees
11 Jan - 12 Jan
West Loop Living – Bright 1BR

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.8 out of 10, Exceptional, (11)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$490
HK$1,312 total
includes taxes & fees
11 Jan - 12 Jan
Modern Comfort: 1BR Unit w/ Laundry

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,312 total
includes taxes & fees
15 Jan - 16 Jan
The One: A 1BR Stay That Feels Like Home

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$490
HK$1,312 total
includes taxes & fees
11 Jan - 12 Jan
Sun-Drenched 1BR Apartment

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
The price is HK$873
HK$1,896 total
includes taxes & fees
2 Feb - 3 Feb
Stylish Japanese-Themed 2BR Apt Close to Downtown

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$817
HK$2,484 total
includes taxes & fees
18 Jan - 19 Jan
River North Rooftop With In and Out Parking 3

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town

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, (19)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$537
HK$1,483 total
includes taxes & fees
11 Jan - 12 Jan
Twice as Nice: Chic 2BR Stay with Style & Space

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$490
HK$1,312 total
includes taxes & fees
11 Jan - 12 Jan
Complete 1BR Home Sum

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$444
HK$1,179 total
includes taxes & fees
11 Jan - 12 Jan
Modern Studio Near UChicago

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (49)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is HK$449
HK$1,929 total
includes taxes & fees
13 Jan - 14 Jan
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
Irving Park
10.0 out of 10, Exceptional, (4)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
The price is HK$547
HK$1,511 total
includes taxes & fees
7 Jan - 8 Jan
Pine Beam Sloth Apartment next to Blue Line

Majestic Modern Style|13 mins DT|4 mins Lake

Majestic Modern Style|13 mins DT|4 mins Lake
Uptown
9.4 out of 10, Exceptional, (13)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
The price is HK$421
HK$1,914 total
includes taxes & fees
7 Jan - 8 Jan
Majestic Modern Style|13 mins DT|4 mins Lake

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
9.4 out of 10, Exceptional, (10)
"Good for family, enjoyed the stay"
United States
Karthik
ENVITAE Hotel 4 Bedroom Luxury Apartments
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

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Hillside offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.