Photo by Off The Beaten Track

Hillside Holiday Rentals

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Check prices for these dates

Tonight
25 Jan - 26 Jan
Tomorrow
26 Jan - 27 Jan
Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb

Holiday Rentals in Hillside

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (663)
"Sandra and Joy are welcoming and helpful. Great front desk."
The price is S$213
includes taxes & fees
27 Jan - 28 Jan
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (421)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is S$152
includes taxes & fees
25 Feb - 26 Feb
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (245)
"New. Modern. Cozy.Clean & quiet place. Will book it again!"
The price is S$110
includes taxes & fees
18 Feb - 19 Feb
Sonder Market Hall
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (353)
"Great property. Quick check in and in great location. Will definitely come back "
Kasa Magnificent Mile Chicago
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (133)
"If you are a walker and just want to explore what Chicago has to offer please book this place. You can store your bags before and after checkin/out and the lobby is so nice and quiet. "
The price is S$198
includes taxes & fees
10 Feb - 11 Feb
Sonder The Burnham Apartments
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (183)
"It was a Great option, straight and contactless."
The price is S$191
includes taxes & fees
17 Feb - 18 Feb
Found Chicago powered by Sonder
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (285)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is S$293
includes taxes & fees
27 Jan - 28 Jan
Level Chicago – Old Town
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (123)
"This property was so clean and safe with so many options to eat parking was easy with the parking app. I cannot wait to stay here again. I was at peace. No one was loud or obnoxious. It was perfect if you’re second-guessing this property don’t it’s so convenient and very easy to check in and out of Little Italy was the best. Thank you for such a great experience. Oh, and the heater above the door as you walk in is amazing as well. Lol"
The Neighborhood Hotel-Little Italy
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."
The price is S$162
includes taxes & fees
18 Feb - 19 Feb
Sonder Jewelers Row
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is S$182
includes taxes & fees
2 Feb - 3 Feb
Sonder The Opal
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (88)
"Loved the location. "
The price is S$163
includes taxes & fees
23 Feb - 24 Feb
Sonder The Plymouth
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (36)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is S$208
includes taxes & fees
24 Feb - 25 Feb
Sonder Greektown
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (251)
"It was great. Place was clean. Stocked with essentials. Great place to be. Would definitely stay here again"
Kasa South Loop Chicago
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (118)
"It was nice, comfortable and close to everything downtown."
The price is S$149
includes taxes & fees
27 Jan - 28 Jan
Kasa River North Chicago
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is S$183
includes taxes & fees
27 Jan - 28 Jan
Wrigleyville Suites
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
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.
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Other types of properties in Hillside you may be interested in

Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8435)
"Good customer service and very clean"
The price is S$147
includes taxes & fees
27 Jan - 28 Jan
Congress Plaza Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (2598)
"Great stay, easy and convenient."
The price is S$156
includes taxes & fees
5 Feb - 6 Feb
citizenM Chicago Downtown
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3729)
"Enjoyed our stay. The hotel is a no frills hotel but the location is hard to beat right on the river. Our room had a fantastic view and was clean. We stayed two nights and both days housekeeping came around and refreshed towels and cleaned up. Overall we would come back to the River Hotel."
The price is S$134
includes taxes & fees
25 Feb - 26 Feb
River Hotel
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.

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 Drury Lane Theater, or get outdoors into nature at a spot like Millennium Park. Other popular places to visit in the area include Michigan Avenue and Wrigley Field.

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.