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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Hillside vacation rentals

Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (8 reviews)
"Excellent, clean, modern, fully furnished apartment in downtown Chicago that is a short car ride or walk to anything you need or want to visit. The neighborhood and building are very safe and the covered parking is well worth the extra expense. We loved the extra space to spread out and the skyline views were beautiful at night. The staff responded right away to any questions we had and even helped to accommodate us an extra night when an event kept us in town longer. The beds were comfortable...
United States
Kathryn
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Smart TV

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 ￥17,217
￥43,837 total
includes taxes & fees
Jul 29 - Jul 30
Luxury Retreat w/ King Bed, 3-in-1 Pool Table, 15 Min to Chicago, Free Parking
Dining

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

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
8.8 out of 10, Excellent, (3 reviews)
"I called the host about the thermostat not working and he said he would get in touch with somebody, never heard back from him and the problem was never solved. There were two window air conditioning units that I cleaned the filters myself as they were not very efficient."
United States
Raymond
The price is ￥12,986
￥64,083 total
includes taxes & fees
Jul 28 - Jul 29
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Interior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
The price is ￥69,063
￥137,238 total
includes taxes & fees
Jul 21 - Jul 22
Modern 3BR Apartment Near North Ave Shops
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, (20 reviews)
"Great host and had everything you would need."
United States
Mj2green J.
The price is ￥24,318
￥29,485 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Exterior

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"2nd stay. Will stay again"
United States
Rusty D.
The price is ￥29,182
￥52,404 total
includes taxes & fees
Jul 29 - Jul 30
✽ Charming Cottage ✽ close to College/Town/Station
1 bedroom

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago

Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Chicago
9.6 out of 10, Exceptional, (28 reviews)
"Nice, clean, and a quiet hotel"
United States
Anonymous traveler
The price is ￥17,034
￥18,847 total
includes taxes & fees
Aug 12 - Aug 13
Cozy King bed,Nsmk|Kitchen|Shower|Studio 6 Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,216 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
The price is ￥23,250
￥32,060 total
includes taxes & fees
Aug 17 - Aug 18
Sentral Michigan Avenue
Smart TV

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
8.0 out of 10, Very Good, (29 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is ￥24,075
￥48,823 total
includes taxes & fees
Jul 20 - Jul 21
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is ￥47,015
￥103,045 total
includes taxes & fees
Jul 19 - Jul 20
River North Rooftop With In and Out Parking 3
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
The price is ￥28,533
￥38,100 total
includes taxes & fees
Jul 19 - Jul 20
LIVN West Loop Chicago Classic Queen Studio
Smart TV, computer monitors

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, (2 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 ￥11,527
￥69,370 total
includes taxes & fees
Jul 19 - Jul 20
3BR Near O'Hare • Office • Coffee Bar • Sleeps 9
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, (17 reviews)
"Great place! "
United States
Isabella T.
The price is ￥21,886
￥41,277 total
includes taxes & fees
Jul 20 - Jul 21
Just remodeled apartment close to airport and mall
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is ￥33,397
￥44,611 total
includes taxes & fees
Jul 19 - Jul 20
LIVN Millennium Park Downtown Chicago Prem Studio
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, (67 reviews)
"Very nice stay. Close to everything. Host very helpful. "
United States
Tamela S.
The price is ￥18,384
￥41,645 total
includes taxes & fees
Jul 28 - Jul 29
Chic Suite/Mins to L Train /Laundry/Free Parking
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (30 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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, (105 reviews)
"Everything was good!"
United States
Brio
The price is ￥24,221
￥50,000 total
includes taxes & fees
Jul 28 - Jul 29
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
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, (86 reviews)
"Great place to stay. Within walking distance to breweries and restaurants. "
United States
Carrie K.
The price is ￥45,231
￥86,617 total
includes taxes & fees
Aug 6 - Aug 7
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
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, (9 reviews)
"Great stay. Nice place. Easy access. Clean. "
United States
Juan S.
The price is ￥20,322
￥42,549 total
includes taxes & fees
Jul 20 - Jul 21
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (87 reviews)
"Wonderful hosts…very kind and communicative. Awesome area… highly recommended!"
United States
Andrew C.
The price is ￥25,939
￥42,409 total
includes taxes & fees
Aug 16 - Aug 17
Cozy studio in Andersonville Chicago
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"what a great location, and the rooftop bar was sensational. Service was friendly and solid, breakfast was enough to last you till dinner, and the rooms (especially the showers) were great."
Janna 3-night trip
Posted less than an hour ago
Hotel Riu Plaza Chicago

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?

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 United Center and Wrigley 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.