Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Hillside vacation rentals

TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
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 ￥15,505
￥32,843 total
includes taxes & fees
Feb 24 - Feb 25
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"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 traveler
The price is ￥15,505
￥33,607 total
includes taxes & fees
Feb 25 - Feb 26
Sleek 1BR Apartment w/ In-unit Laundry
Interior

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 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 ￥20,932
￥56,167 total
includes taxes & fees
Mar 1 - Mar 2
River North Rooftop With In and Out Parking 3
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥15,505
￥33,607 total
includes taxes & fees
Feb 26 - Feb 27
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (7 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 ￥15,505
￥32,843 total
includes taxes & fees
Feb 24 - Feb 25
West Loop Living – Bright 1BR
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"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 ￥15,505
￥31,292 total
includes taxes & fees
Feb 24 - Feb 25
Chic Studio in the Heart of the Gold Coast
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (184 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Interior

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (4 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is ￥14,730
￥19,076 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
TV, offices

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (16 reviews)
"Nice location "
United States
tom b.
The price is ￥12,404
￥31,536 total
includes taxes & fees
Mar 5 - Mar 6
Cozy & Furnished 2BR Unit
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥22,304
￥61,515 total
includes taxes & fees
Feb 24 - Feb 25
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
1 bedroom, WiFi, bed sheets

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 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥17,521
￥35,969 total
includes taxes & fees
Mar 1 - Mar 2
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.2 out of 10, Very Good, (14 reviews)
"Great location! "
United States
Kourtney K.
The price is ￥13,489
￥33,582 total
includes taxes & fees
Feb 24 - Feb 25
Your Perfect 2BR Home
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,091 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥17,003
￥24,509 total
includes taxes & fees
Feb 24 - Feb 25
Sentral Michigan Avenue
Interior

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very Good, (32 reviews)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is ￥13,815
￥34,452 total
includes taxes & fees
Feb 26 - Feb 27
Oak Park Queen
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"great stay"
United States
matt R.
The price is ￥10,354
￥31,380 total
includes taxes & fees
Feb 24 - Feb 25
A quiet stay while you are away
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (62 reviews)
"Great room and host"
United States
Kathy T.
The price is ￥9,303
￥21,045 total
includes taxes & fees
Feb 24 - Feb 25
Cozy studio in Andersonville Chicago
2 bedrooms, iron/ironing board, travel crib, WiFi

Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
9.4 out of 10, Exceptional, (9 reviews)
"The location was ideal for us and had a grocery store, a Starbucks and CVS close by . The neighborhood was safe for walking around . Beds comfortable and whole place was very clean . I would stay here again . "
United States
Sharlene T.
The price is ￥10,698
￥29,538 total
includes taxes & fees
Feb 24 - Feb 25
Homey 2BR Apt w/ Parking
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (26 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is ￥9,768
￥26,123 total
includes taxes & fees
Feb 24 - Feb 25
Nice 1BR Spot, Unwind & Relax
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥13,815
￥40,006 total
includes taxes & fees
Feb 24 - Feb 25
2-bedroom apartment just 2 minutes drive to Wrigley Field
1 bedroom, iron/ironing board, travel crib, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is ￥9,768
￥26,123 total
includes taxes & fees
Feb 24 - Feb 25
Charming Sunlit 1BR Apartment
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

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent
"."
Rafael 2-night trip
Posted 8 hours ago
Courtyard by Marriott Chicago 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 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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This vacation home rental outside of Hillside is located on a lake and has a fireplace, a patio, and a barbecue grill 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 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 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.