A lush green valley with a winding road, steep mountains, and a misty atmosphere.

Hillside Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Hillside vacation rentals

Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is AED 1,032
AED 2,361 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

2MI to Obama Center - Pet-Friendly near UOC!

2MI to Obama Center - Pet-Friendly near UOC!
Woodlawn
10.0 out of 10, Exceptional, (2 reviews)
"Great host very accommodating."
United States
Kali P.
The price is AED 327
AED 1,239 total
includes taxes & fees
3 Jul - 4 Jul
2MI to Obama Center - Pet-Friendly near UOC!
Property grounds

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (84 reviews)
"Great location for a short trip "
United States
Eric W.
The price is AED 526
AED 1,261 total
includes taxes & fees
5 Jul - 6 Jul
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is AED 481
AED 656 total
includes taxes & fees
2 Jul - 3 Jul
LIVN West Loop Chicago Queen Superior Studio
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
The price is AED 590
AED 800 total
includes taxes & fees
5 Jul - 6 Jul
Sentral Michigan Avenue
Dining

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Berwyn
9.8 out of 10, Exceptional, (30 reviews)
"great stay for the guys."
United States
Louise D.
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Terrace/patio

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (50 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is AED 413
AED 925 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Paper towels

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Great place! "
United States
Isabella T.
The price is AED 496
AED 931 total
includes taxes & fees
4 Jul - 5 Jul
Just remodeled apartment close to airport and mall
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (51 reviews)
"Great stay"
United States
Steve T.
The price is AED 661
AED 1,352 total
includes taxes & fees
7 Jul - 8 Jul
LUXE 3 BR, 2 BA + Hot Tub
Exterior

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is AED 661
AED 1,148 total
includes taxes & fees
26 Jul - 27 Jul
✽ Charming Cottage ✽ close to College/Town/Station
Interior

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

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
9.8 out of 10, Exceptional, (19 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is AED 551
AED 668 total
includes taxes & fees
2 Jul - 3 Jul
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Interior

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (101 reviews)
"Everything was good!"
United States
Brio
The price is AED 552
AED 1,153 total
includes taxes & fees
6 Jul - 7 Jul
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Interior

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (8 reviews)
"Great stay. Nice place. Easy access. Clean. "
United States
Juan S.
The price is AED 440
AED 943 total
includes taxes & fees
8 Jul - 9 Jul
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Living area

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking

Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Oak Park
The price is AED 446
AED 595 total
includes taxes & fees
23 Jul - 24 Jul
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is AED 566
AED 755 total
includes taxes & fees
2 Jul - 3 Jul
LIVN Millennium Park Downtown Chicago Studio
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 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 AED 973
AED 2,208 total
includes taxes & fees
6 Jul - 7 Jul
River North Rooftop With In and Out Parking 3
Smart TV, books

Chic Suite/Mins to L Train /Laundry/Free Parking

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (65 reviews)
"This was a very cute apartment in a really nice neighborhood! We got a little confused about check-in because the parking space and the lockbox are not clearly marked. A couple of big, comfy couches in the living room would have made it a little more comfortable for 2 adults and 2 tall teenagers. Otherwise it was perfect and we would definitely stay again."
United States
Erin
The price is AED 470
AED 992 total
includes taxes & fees
28 Jul - 29 Jul
Chic Suite/Mins to L Train /Laundry/Free Parking
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, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is AED 430
AED 757 total
includes taxes & fees
28 Jul - 29 Jul
Cozy studio in Andersonville Chicago
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Our stay was very comfortable. Communication was fantastic and super timely. The kitchen was well stocked. The house was very clean and spacious. Would definitely stay there again!"
United States
Erin B.
The price is AED 702
AED 1,465 total
includes taxes & fees
9 Jul - 10 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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
"Good stay. Nice bang for the buck and in a cool part of town."
Brandon 2-night trip
Posted 1 hour ago
Eurostars Magnificent Mile

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Hillside is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.