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19 Sep - 21 Sep
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26 Sep - 28 Sep
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10 Oct - 12 Oct
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7 Nov - 9 Nov

Vacation Homes in Hillside

Our top choices for Hillside vacation homes

The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very Good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is SAR 409
SAR 858 total
includes taxes & fees
21 Sep - 22 Sep
The One: A 1BR Stay That Feels Like Home
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is SAR 390
SAR 812 total
includes taxes & fees
22 Sep - 23 Sep
Stylish 1BR in West Loop
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Sun-Drenched 1BR Apartment

The price is SAR 390
SAR 812 total
includes taxes & fees
22 Sep - 23 Sep
Sun-Drenched 1BR Apartment
Relaxing Chicago Studio
Desk, iron/ironing board, WiFi, bed sheets

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (10)
"Had a great stay. Great location. "
The price is SAR 356
SAR 741 total
includes taxes & fees
24 Sep - 25 Sep
Relaxing Chicago Studio
Prime City Stay in a 1BR Apt
1 bedroom, iron/ironing board, travel crib, WiFi

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
"Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit."
The price is SAR 293
SAR 698 total
includes taxes & fees
7 Oct - 8 Oct
Prime City Stay in a 1BR Apt
Cozy house in the city
Outdoor dining

Cozy house in the city

2.0 star property
9.0 out of 10, Wonderful, (4)
"10/10 would recommend again!"
Cozy house in the city
Peaceful 1BR Escape in Evanston
1 bedroom, iron/ironing board, travel crib, WiFi

Peaceful 1BR Escape in Evanston

9.4 out of 10, Exceptional, (3)
"Quiet, clean and spacious! A peaceful neighborhood. "
The price is SAR 330
SAR 730 total
includes taxes & fees
15 Sep - 16 Sep
Peaceful 1BR Escape in Evanston
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Interior

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

10.0 out of 10, Exceptional, (1)
"The house was amazing. The beds were so comfortable. The stay was so fun. Thank you for everything!"
The price is SAR 248
SAR 1,405 total
includes taxes & fees
24 Sep - 25 Sep
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill
Comfortable 2BR Chicago Apt
2 bedrooms, iron/ironing board, WiFi, bed sheets

Comfortable 2BR Chicago Apt

9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
The price is SAR 330
SAR 798 total
includes taxes & fees
17 Sep - 18 Sep
Comfortable 2BR Chicago Apt
Homey 1BR Space Apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

Homey 1BR Space Apartment

9.2 out of 10, Wonderful, (5)
"This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night."
The price is SAR 319
SAR 729 total
includes taxes & fees
29 Sep - 30 Sep
Homey 1BR Space Apartment
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

7.6 out of 10, Good, (10)
"Comfy beds and a great house for kids and adults."
The price is SAR 214
SAR 1,862 total
includes taxes & fees
30 Sep - 1 Oct
4BR Retreat w/ Theater, Game Room & Backyard
Chic Studio in Heart of Chicago
Fridge, oven, stovetop, coffee/tea maker

Chic Studio in Heart of Chicago

10.0 out of 10, Exceptional, (2)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
The price is SAR 330
SAR 742 total
includes taxes & fees
1 Oct - 2 Oct
Chic Studio in Heart of Chicago
Chic apartment with fitness room and AC in beautiful Chicago
Exterior

Chic apartment with fitness room and AC in beautiful Chicago

6.8 out of 10, (3)
"Didn’t receive check in information until after book in time. This was after repeated messages, calls to property manager & VRBO. The actual apartment was tidy, however the drain in the tub was clogged. Parking was difficult and when asked if we could park in the lot behind the apartment, we were told it was 20 more a day. Was allowed to park there the second night at no cost. Communication once we were actually checked in was good. It’s in a lovely neighborhood and close to the train and...
The price is SAR 375
SAR 1,167 total
includes taxes & fees
12 Sep - 13 Sep
Chic apartment with fitness room and AC in beautiful Chicago
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

9.6 out of 10, Exceptional, (50)
"Perfect place for an 8 person golf trip! "
The price is SAR 578
SAR 1,238 total
includes taxes & fees
14 Sep - 15 Sep
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Great Layout – Spacious 2BR Apt
Fridge, microwave, oven, stovetop

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (4)
"Clean, comfortable, and would definitely stay again!"
The price is SAR 330
SAR 798 total
includes taxes & fees
17 Sep - 18 Sep
Great Layout – Spacious 2BR Apt
A quiet stay while you are away
Exterior

A quiet stay while you are away

9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
The price is SAR 449
SAR 1,000 total
includes taxes & fees
7 Oct - 8 Oct
A quiet stay while you are away
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop

Getaway Near ORD With Great Local Amenities

8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
The price is SAR 325
SAR 1,106 total
includes taxes & fees
15 Sep - 16 Sep
Getaway Near ORD With Great Local Amenities
Bright & Modern Lakeview Studio
WiFi, bed sheets

Bright & Modern Lakeview Studio

9.6 out of 10, Exceptional, (5)
"This is a great location to hit the Lakeview neighborhood with Wrigley Field just a couple blocks over. When trying to get the check-in instructions, there were a lot of hoops to jump through to get the payment to the management company for this property. I had to contact the host (management company) multiple times to get the links to the forms to upload a driver's license and selfie holding said driver's license. Another URL to get to the payment Venmo account. And another URL for the...
The price is SAR 345
SAR 722 total
includes taxes & fees
1 Oct - 2 Oct
Bright & Modern Lakeview Studio
Oak Park, IL, entire house, short walk to train.
Fridge, microwave, oven, stovetop

Oak Park, IL, entire house, short walk to train.

9.4 out of 10, Exceptional, (20)
"This place was exactly what we needed, to be close to our daughter in Oak Park. It’s conveniently located and quite spacious. Communication with Jay was prompt and easy."
The price is SAR 419
SAR 1,150 total
includes taxes & fees
24 Sep - 25 Sep
Oak Park, IL, entire house, short walk to train.
Cozy Studio in Portage Park
Iron/ironing board, travel crib, WiFi, bed sheets

Cozy Studio in Portage Park

The price is SAR 330
SAR 705 total
includes taxes & fees
17 Sep - 18 Sep
Cozy Studio in Portage Park
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Nice"
Eros 2-night trip
Posted 17 hours ago
The Chicago Hotel Collection - Magnificent Mile