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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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, (65 reviews)
"It was a great home to stay at house was clean, some dirty sheets left on top of washer but other than that everything was good , will definitely come back"
United States
Brenda M
The price is SAR 676
SAR 1,321 total
includes taxes & fees
18 Nov - 19 Nov
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, (28 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 SAR 563
SAR 650 total
includes taxes & fees
15 Nov - 16 Nov
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, (25 reviews)
"We had a great time at this property while our family explored Chicago. We found everything about the property was awesome for our family. Sitting outside with coffee in the morning was fantastic. Quiet neighborhood and very close to grocery store. We would stay there again. If we had to make any recommendations it would be that the living room could use more seating as we were five adults and had to use kitchen chairs for all to have a seat. I would also consider new sofa downstairs. It sits...
United States
Stephen K.
The price is SAR 750
SAR 1,665 total
includes taxes & fees
18 Nov - 19 Nov
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

4. 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, (76 reviews)
"Had an amazing stay and would definitely book again!"
United States
Makenna
The price is SAR 277
SAR 721 total
includes taxes & fees
17 Nov - 18 Nov
Chic Suite/Mins to L Train /Laundry/Free Parking
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is SAR 437
SAR 513 total
includes taxes & fees
17 Nov - 18 Nov
Wrigleyville Suites
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

6. 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, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is SAR 557
SAR 1,082 total
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A dining area with a table set for two, a black leather sofa, and a ceiling fan.

7. 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, (35 reviews)
"Relaxing stay and safe location. Host JD provided great communication throughout the stay. Stores are nearby in case you need items for your trip. Food options are abundant in the area. 30 min drive to downtown Chicago."
United States
Cynthia M.
The price is SAR 269
SAR 662 total
includes taxes & fees
17 Nov - 18 Nov
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
A modern living room with a blue sofa, a patterned rug, and a television.

8. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is SAR 225
SAR 725 total
includes taxes & fees
16 Nov - 17 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

9. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
The price is SAR 230
SAR 279 total
includes taxes & fees
13 Dec - 14 Dec
King Bed Non-Smoking
A rooftop terrace with a brick wall, large windows, and a metal railing.

10. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is SAR 281
SAR 979 total
includes taxes & fees
17 Nov - 18 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

11. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is SAR 385
SAR 1,608 total
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

12. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is SAR 371
SAR 1,255 total
includes taxes & fees
21 Nov - 22 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

13. 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 SAR 277
SAR 307 total
includes taxes & fees
13 Dec - 14 Dec
2 Full Beds | Non-Smoking, Kitchen
A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

14. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (93 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is SAR 570
SAR 901 total
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A glass elevator with a city view.

15. 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 SAR 392
SAR 904 total
includes taxes & fees
17 Nov - 18 Nov
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
A living room with a white sofa, a decorative vase with a plant, a small wooden figurine, and a gold decorative piece on a white coffee table.

16. 3BR Near O'Hare • Office • Coffee Bar • Sleeps 9

3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
O'Hare
10.0 out of 10, Exceptional, (7 reviews)
"The space was comfortable, clean and inviting.The host was fabulous! I recommend this place when visiting the Chicago area."
United States
Megan K.
The price is SAR 360
SAR 1,706 total
includes taxes & fees
1 Dec - 2 Dec
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

17. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is SAR 232
SAR 1,364 total
includes taxes & fees
15 Nov - 16 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A modern bedroom with a bed, a sofa, and a hanging plant.

18. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is SAR 270
SAR 491 total
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago
A modern apartment with a living room, kitchen, and a large window with curtains.

19. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
8.8 out of 10, Excellent, (20 reviews)
"READ THE FULL LISTING BEFORE YOU BOOK!! I've never had to jump through so many hoops to book a room before! Then they reached out multiple times via Vrbo messaging, texting and now a phone call requesting a 5 star review. What a pain just for a room to sleep in after a concert at Wrigley!With that said, the space was great! Clean, comfy and looked to have all of the essentials should you need to use the apartment more than we did."
United States
Heather B.
The price is SAR 281
SAR 979 total
includes taxes & fees
17 Nov - 18 Nov
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
A hotel room with a large bed, a desk, a chair, a lamp, and artwork on the wall.

20. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is SAR 287
SAR 642 total
includes taxes & fees
15 Nov - 16 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Very much enjoyed our stay. Staff was amazing!! Breakfast was excellent."
Frances 3-night trip
Posted 2 hours ago
Fairmont Chicago at Millennium Park

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.