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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Hillside vacation rentals

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

1. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is AED 661
AED 1,367 total
includes taxes & fees
26 Oct - 27 Oct
LUXE 3 BR, 2 BA + Hot Tub
A modern living room with teal sofas, a coffee table, and a TV.

2. 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, (25 reviews)
"The room was very clean, and the host was timely with communications. The couches and bed were so comfy!"
United States
Kaitlyn W.
The price is AED 477
AED 589 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

3. 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
9.6 out of 10, Exceptional, (24 reviews)
"Great place Great location "
United States
Josh W.
The price is AED 875
AED 1,880 total
includes taxes & fees
20 Oct - 21 Oct
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

4. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AED 545
AED 1,110 total
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Lake

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is AED 657
AED 1,000 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

6. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (82 reviews)
"Excellent place to stay!"
United States
Alicia K.
The price is AED 407
AED 1,100 total
includes taxes & fees
26 Oct - 27 Oct
Cozy, Comfortable and Convenient apartment. Close to everything!
A modern building with the name 'SENIORAL' prominently displayed on the facade.

7. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is AED 526
AED 617 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

8. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (287 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is AED 845
AED 967 total
includes taxes & fees
12 Nov - 13 Nov
The Gem Museum Suites
Terrace/patio

9. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is AED 782
AED 1,303 total
includes taxes & fees
25 Oct - 26 Oct
At Home in Oak Park
A modern kitchen with stainless steel appliances, a dining area with a wooden table and chairs, and a large cityscape painting on the wall.

10. Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Villa Park
8.6 out of 10, Excellent, (10 reviews)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
The price is AED 859
AED 1,861 total
includes taxes & fees
26 Oct - 27 Oct
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.4 out of 10, Exceptional, (73 reviews)
"Easy access to the Green Line."
United States
Michael
The price is AED 354
AED 867 total
includes taxes & fees
26 Oct - 27 Oct
Chic Suite/Mins to L Train /Laundry/Free Parking
Private kitchen

12. 1BR Apartment - Walk to Shops - Downtown OAK PARK

1BR Apartment - Walk to Shops - Downtown OAK PARK
Oak Park
9.2 out of 10, Wonderful, (44 reviews)
"Great location! Enjoyed my stay!"
United States
Shannon H.
The price is AED 411
AED 942 total
includes taxes & fees
27 Oct - 28 Oct
1BR Apartment - Walk to Shops - Downtown OAK PARK
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

13. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is AED 658
AED 1,161 total
includes taxes & fees
27 Oct - 28 Oct
Historic Oak Park Home
A modern kitchen with a large island, bar stools, and a city view.

14. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is AED 1,028
AED 1,298 total
includes taxes & fees
3 Nov - 4 Nov
Level Chicago – Old Town
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

15. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveler
The price is AED 258
AED 286 total
includes taxes & fees
30 Oct - 31 Oct
2 Full Beds | Non-Smoking, Kitchen
A glass elevator with a city view.

16. 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, (115 reviews)
"Excellent communication from the host, we also appreciated their modern, organized and clean home."
United States
Robin D.
The price is AED 496
AED 1,072 total
includes taxes & fees
27 Oct - 28 Oct
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

17. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (69 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is AED 377
AED 779 total
includes taxes & fees
2 Nov - 3 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

18. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AED 624
AED 989 total
includes taxes & fees
27 Oct - 28 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

19. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is AED 652
AED 1,154 total
includes taxes & fees
27 Oct - 28 Oct
The Oak Park Loft
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

20. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
Private Workspace • Sleeps4 • Modern Stylish Stay
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

8/10 Good
"veru convenient for early flights from share."
arvind 1-night trip
Posted 3 hours ago
Hilton Chicago O'Hare Airport

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 Soldier Field.

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.