Hillside Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Hillside holiday rentals

Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,104 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$925
HK$1,315 total
includes taxes & fees
19 Mar - 20 Mar
Sentral Michigan Avenue
Interior

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 out of 10, Exceptional, (4 reviews)
"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$1,526
HK$3,529 total
includes taxes & fees
18 Mar - 19 Mar
River North Rooftop With In and Out Parking 3
Full-sized fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (441 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (186 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
TV, offices

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$884
HK$1,825 total
includes taxes & fees
12 Mar - 13 Mar
Modern Comfort: 1BR Unit w/ Laundry
TV, offices

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2 reviews)
"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$884
HK$1,834 total
includes taxes & fees
17 Mar - 18 Mar
Sun-Drenched 1BR Apartment
Room

Apartment in Downtown Chicago

Modern 4BR Gold Coast Duplex w/ Jacuzzi & Balcony
The price is HK$2,738
HK$6,166 total
includes taxes & fees
18 Mar - 19 Mar
Modern 4BR Gold Coast Duplex w/ Jacuzzi & Balcony
TV, offices

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 6
10.0 out of 10, Exceptional, (15 reviews)
"Great place"
United States
Daniel L.
The price is HK$1,815
HK$3,887 total
includes taxes & fees
19 Mar - 20 Mar
Modern West Loop Gem-City Views & Prime Location 6
1 bedroom, iron/ironing board, travel cot, WiFi

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (8 reviews)
"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$884
HK$1,825 total
includes taxes & fees
15 Mar - 16 Mar
West Loop Living – Bright 1BR
Desk, iron/ironing board, travel cot, WiFi

Apartment in Downtown Chicago

Chic Studio in the Heart of the Gold Coast
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is HK$970
HK$1,799 total
includes taxes & fees
24 Mar - 25 Mar
Chic Studio in the Heart of the Gold Coast
Interior

Apartment in South Evanston

Modern|Aesthetic|2BR|Evanston|Next to Beach
8.6 out of 10, Excellent, (26 reviews)
"Amazing location. Completely thrilled with our choice of this beautiful place. Thank you!"
United States
Emily M.
The price is HK$2,346
HK$4,008 total
includes taxes & fees
16 Mar - 17 Mar
Modern|Aesthetic|2BR|Evanston|Next to Beach
Interior

Holiday Home in Oak Park

Chic 3bed 2bath Home with free parking close to United Center
9.8 out of 10, Exceptional, (18 reviews)
"Plenty of space for my family and loved the onsite free parking, that was helpful because we drove everywhere, just a 30 min drive into the heart of the city"
United States
Jessica T.
The price is HK$1,760
HK$5,302 total
includes taxes & fees
12 Mar - 13 Mar
Chic 3bed 2bath Home with free parking close to United Center
1 bedroom, WiFi, bed sheets

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$884
HK$1,834 total
includes taxes & fees
17 Mar - 18 Mar
1BR Modern Luxe Apt with In-Unit Laundry
TV

Condo in Lakeview

Wrigley Field All Star Suite 3 Bedrooms 2 Bath
9.4 out of 10, Exceptional, (22 reviews)
"Everything was excellent. Highly recommended!!!"
United States
Donald S.
The price is HK$2,964
HK$7,488 total
includes taxes & fees
30 Mar - 31 Mar
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Smart TV, fireplace, books, video library

Holiday Home in Skokie

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is HK$2,597
HK$5,491 total
includes taxes & fees
30 Mar - 31 Mar
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Exterior

Holiday Home in Oak Park

A quiet stay while you are away
9.8 out of 10, Exceptional, (34 reviews)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is HK$754
HK$1,884 total
includes taxes & fees
18 Mar - 19 Mar
A quiet stay while you are away
Interior

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 3
10.0 out of 10, Exceptional, (5 reviews)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is HK$1,713
HK$3,742 total
includes taxes & fees
30 Mar - 31 Mar
Modern West Loop Gem-City Views & Prime Location 3
Interior

Apartment in Near West Side

Your Perfect 2BR Home
8.4 out of 10, Very good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is HK$845
HK$1,935 total
includes taxes & fees
16 Mar - 17 Mar
Your Perfect 2BR Home
Exterior detail

Holiday Home in Oak Park

Oak Park Victorian by FLW Studio
10.0 out of 10, Exceptional, (29 reviews)
"Finding a good 3 br or 4 br option in and around OP / RF is challenging and if this one is available, jump on it. Functional plan, easy parking, great location and responsive owners. "
United States
Lawrence P.
The price is HK$1,557
HK$4,236 total
includes taxes & fees
18 Mar - 19 Mar
Oak Park Victorian by FLW Studio
Interior

Aparthotel in West Town

Cabin 105 by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is HK$527
HK$1,589 total
includes taxes & fees
15 Mar - 16 Mar
Cabin 105 by 747 Lofts
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Awesome area"
Zachary 3-night trip
Posted 2 hours ago
Eurostars Magnificent Mile

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.