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Hillside Vacation Rentals

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Vacation Rentals in Hillside

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (844)
"We would stay here again. Very happy with our stay "
The price is P10,149
P13,591 total
includes taxes & fees
Aug 4 - Aug 5
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (334)
"The property canceled on us 4 hours prior to check in"
The price is P7,236
P8,494 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (331)
"Hotel was nice"
The price is P14,860
P18,719 total
includes taxes & fees
Aug 24 - Aug 25
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (452)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (590)
"I would stay again. "
The price is P8,158
P9,577 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (124)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P7,964
P9,349 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (321)
"I definitely enjoyed my stay and roof deck was the highlight. "
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (199)
"Clean, new, spacious "
The price is P12,966
P15,220 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (80)
"Had a good and comfortable stay "
The price is P11,877
P13,597 total
includes taxes & fees
Aug 5 - Aug 6
The Gem Museum Suites

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (180)
"Building was quiet. Good nearby restaurants. "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is P9,178
P10,774 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (157)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Wrigleyville Suites

2.0 star property
9.8 out of 10, Exceptional, (10)
"Excellent location and very clean! Would stay again!"
The price is P5,604
P9,436 total
includes taxes & fees
Jul 29 - Jul 30
Wrigleyville Suites

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is P8,158
P9,577 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is P12,092
P14,194 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy Greektown Apartments

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.2 out of 10, Wonderful, (15)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is P5,359
P10,270 total
includes taxes & fees
Aug 12 - Aug 13
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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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.