Photo by Off The Beaten Track

Hillside Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Hillside

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (881)
"Great stay!"
The price is P8,199
P11,301 total
includes taxes & fees
Sep 2 - Sep 3
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (343)
"Great stay!"
The price is P7,229
P8,486 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (338)
"A lot of good food options walkable distance. "
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (471)
"Great location and great property will stay again "
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (190)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (618)
"I would stay again. "
The price is P6,258
P7,347 total
includes taxes & fees
Sep 2 - Sep 3
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (207)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is P8,684
P10,194 total
includes taxes & fees
Sep 2 - Sep 3
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (83)
"Super nice hotel and staff "
The price is P11,712
P13,408 total
includes taxes & fees
Sep 2 - Sep 3
The Gem Museum Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P9,589
P11,256 total
includes taxes & fees
Sep 2 - Sep 3
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (173)
"Great location!!!"
The price is P7,714
P9,055 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (14)
"Excellent location and very clean! Would stay again!"
The price is P4,726
P8,402 total
includes taxes & fees
Aug 19 - Aug 20
Wrigleyville Suites

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (46)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is P7,229
P8,486 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (163)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"Great location, easy stay!"
The price is P12,080
P14,181 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy Greektown Apartments

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (16)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is P4,381
P13,742 total
includes taxes & fees
Aug 21 - Aug 22
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillside Hotel Reviews

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.