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Hillside Holiday Rentals

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Holiday Rentals in Hillside

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (405)
"The check in was flawless and got to an impecable room."
The price is NZ$287
per night
28 May - 29 May
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (83)
"Extremely clean and very modern room, very impressed with the quality and how easy it is to check in and get into a room. Highly recommend and will definitely come back in the future."
The price is NZ$181
per night
27 May - 28 May
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (297)
"Overall the stay was amazing. We will definitely be booking here again."
The price is NZ$371
per night
28 May - 29 May
Sonder South Wabash
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49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (228)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (128)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$407
per night
18 Jun - 19 Jun
Found Chicago powered by Sonder
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is NZ$390
per night
27 May - 28 May
Level Chicago – Old Town
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (57)
"It is next to Union Station. Downtown attractions are across the bridge. We loved the industrial decor. The wall is thin. You can hear people talking. It doesn’t bother us too much. Love Sonder!"
The price is NZ$373
per night
28 May - 29 May
Sonder The Burnham
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (30)
"This is one of the best hotels I have ever stayed. Very clean, spacious, and everything is well-designed. Exceed my expectation in every aspect."
The Neighborhood Hotel-Little Italy
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is NZ$125
per night
22 May - 23 May
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (101)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is NZ$377
per night
28 May - 29 May
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$456
per night
19 Jun - 20 Jun
Sonder The Plymouth
3 bedrooms, WiFi, bed sheets
Your Home Away From Home
2.0 out of 10, (1)
"No me agradó"
The price is NZ$282
per night
2 Jun - 3 Jun
Your Home Away From Home
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is NZ$342
per night
28 May - 29 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"Convenient location. Clean, modern style. Everything was excellent!"
Wrigley/Southport Corridor Garden Oasis +parking!
Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Don't see what you're looking for?
See all available properties in Hillside
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.

Other types of properties in Hillside you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6786)
"All has gone as planned. Check in was quick and the ice machine on the 7th floor works. What a bonus."
The price is NZ$286
per night
28 May - 29 May
Congress Plaza Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2898)
"Nice hotel and location "
The price is NZ$327
per night
27 May - 28 May
River Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2600)
"Large, super clean, convenient hotel. Staff was excellent and friedly. Bar staff was great. Would definitely stay again."
The price is NZ$240
per night
27 May - 28 May
Warwick Allerton - 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hillside holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hillside. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Hillside. Seeing all the best attractions is bound to make you fall in love with Hillside. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Hillside short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Hillside?

Yes, there are holiday rentals close to the most popular sights in Hillside, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and forests in Hillside. Allow some time to check out the shops during your trip.

What can I see and do in Hillside?

Enjoy the area's cultural attractions such as Art Institute of Chicago, or get outdoors into nature at a spot like Grant Park. Other popular places to visit in the area include Wrigley Field and Navy Pier.

What are holiday rentals like in Hillside?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillside. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.

Recent reviews of Hillside properties
Expedia verified reviews