Photo by Off The Beaten Track

Hillside Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 18 - Nov 19
Tomorrow
Nov 19 - Nov 20
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Hillside

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (986)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P5,938
P8,700 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (623)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (383)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (402)
"Great location. Was there for the marathon and had a great stay. "
United States
HELGA
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (375)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (254)
"Great stay. "
United States
Teresa
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
Near South Side
8.6 out of 10, Excellent, (713)
"Love the unit and location close to multiple restaurants and shopping."
United States
Jessie
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (57)
"Worked great for a work and family trip."
United States
David
Sonder by Marriott Bonvoy The Opal Apartments River North
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (188)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Front of property
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (219)
"Perfect location and area was wonderful."
United States
Thomas
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.4 out of 10, Exceptional, (27)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is P4,571
P5,366 total
includes taxes & fees
Nov 19 - Nov 20
Wrigleyville Suites
Private kitchen
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is P10,713
P12,264 total
includes taxes & fees
Nov 23 - Nov 24
The Gem Museum Suites
Living room
Sonder by Marriott Bonvoy Greektown Apartments

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
Sonder by Marriott Bonvoy Greektown Apartments
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is P17,089
P20,060 total
includes taxes & fees
Nov 19 - Nov 20
Chicago luxury home suites
Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is P14,673
P23,311 total
includes taxes & fees
Nov 19 - Nov 20
Stylish Apartment near Chicago Downtown
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is P16,286
P38,893 total
includes taxes & fees
Dec 18 - Dec 19
Art Villa
Exterior
Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
West Town
9.0 out of 10, Wonderful, (21)
"The stay lacked in shelf space as well as other amenities that could be useful. "
United States
Zugeily
Ground Floor Studios in Chicago by 747 Lofts
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hillside Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Nice accommodation's and great area, mall And restaurants walking distance "
leticia 3-night trip
Posted 18 hours ago
The Whitehall Hotel, BW Premier Collection

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:

  • View our selection of featured holiday rentals in Hillside
  • Use the map to find apartments and other holiday homes in the Hillside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillside while they last

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 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.