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Apartments in Hillside

Clean & Equipped 1BR Apt

7.6 out of 10, Good, (9)
The price is AED 349
AED 757 total
includes taxes & fees
4 Aug - 5 Aug
Clean & Equipped 1BR Apt

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (8)
The price is AED 349
AED 812 total
includes taxes & fees
6 Aug - 7 Aug
Lakeview 2BR Apartment

Cozy, Fully Set-Up 1BR Space

9.2 out of 10, Wonderful, (7)
"Great place! 15 min walk to Wrigley "
The price is AED 349
AED 757 total
includes taxes & fees
5 Aug - 6 Aug
Cozy, Fully Set-Up 1BR Space

Charming 2BR in Vibrant Lakeview

9.8 out of 10, Exceptional, (6)
The price is AED 360
AED 847 total
includes taxes & fees
11 Aug - 12 Aug
Charming 2BR in Vibrant Lakeview

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (15)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is AED 312
AED 612 total
includes taxes & fees
5 Aug - 6 Aug
Cozy studio in Andersonville Chicago

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (7)
The price is AED 327
AED 740 total
includes taxes & fees
12 Aug - 13 Aug
Nice 1BR Spot, Unwind & Relax

Huge Projector and Designated Workspace - Near Wrigley!

The price is AED 229
AED 1,058 total
includes taxes & fees
13 Aug - 14 Aug
Huge Projector and Designated Workspace - Near Wrigley!

4BR Home – Well-Furnished, Garage Included

5.0 out of 10, (2)
"There we 5 of us. Great location my only suggestion is that the bedrooms needed fans on some sort the master with the 2 double beds had a ceiling fan. The 3rd floor was way to warm. All in a great place. Very comfortable location "
4BR Home – Well-Furnished, Garage Included

Comfy 2BR in Heart of Lakeview

9.0 out of 10, Wonderful, (2)
"Great location for a short stay. Owner answers very quickly and is helpful. Check in and check out are very clear."
The price is AED 360
AED 834 total
includes taxes & fees
11 Aug - 12 Aug
Comfy 2BR in Heart of Lakeview

Your Perfect 2BR Home w/ Parking

8.0 out of 10, Very Good, (4)
"Great location, close to United Center. Our host was super and was able to help me when I couldn't follow the instructions (lol). Wish I could have had a longer stay."
The price is AED 404
AED 922 total
includes taxes & fees
2 Sep - 3 Sep
Your Perfect 2BR Home w/ Parking

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (32)
"Easy to find, slept like a baby. "
The price is AED 657
AED 1,396 total
includes taxes & fees
2 Sep - 3 Sep
2-bedroom apartment just 2 minutes drive to Wrigley Field

Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

8.8 out of 10, Excellent, (33)
"It was what I thought it would be "
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

1BR Apt - Clean & Comfy

9.4 out of 10, Exceptional, (3)
"Great apartment, great location, and excellent host."
The price is AED 349
AED 757 total
includes taxes & fees
4 Aug - 5 Aug
1BR Apt - Clean & Comfy

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

10.0 out of 10, Exceptional, (37)
"This was convenient and check-in process was easy. We would stay here again."
The price is AED 213
AED 836 total
includes taxes & fees
11 Aug - 12 Aug
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

9.0 out of 10, Wonderful, (96)
"Nice property, enjoyed the stay."
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

Spacious 3BR | 2BA Family-Friendly Home

10.0 out of 10, Exceptional, (1)
"Good location! Brewery, coffee shop, sandwich shop and nice restaurants all within walking distance! Host was very responsive"
The price is AED 558
AED 1,184 total
includes taxes & fees
19 Aug - 20 Aug
Spacious 3BR | 2BA Family-Friendly Home

Your 2BR Home in the City

The price is AED 419
AED 893 total
includes taxes & fees
6 Aug - 7 Aug
Your 2BR Home in the City

Upscale 4BR Retreat: Wicker Park

9.4 out of 10, Exceptional, (3)
"Place was clean, safe, parking was easy along side streets. Very spacious and reasonably priced! Will stay again! "
The price is AED 525
AED 1,572 total
includes taxes & fees
4 Aug - 5 Aug
Upscale 4BR Retreat: Wicker Park

Bright & Roomy 4BR in Pilsen

7.4 out of 10, Good, (6)
The price is AED 577
AED 1,641 total
includes taxes & fees
5 Aug - 6 Aug
Bright & Roomy 4BR in Pilsen

Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC

6.0 out of 10, (2)
"The property was great and exactly what we needed for our stay. We had 2 kids and 3 adults. The space was well laid out and the neighborhood was perfect. We could walk easily to grab coffee/snacks plus a grocery store with a park right around the corner. The property manager made check in and out very easy and was easily reached if there were questions!"
Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC
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

What's it like to stay at an apartment in Hillside?
There are plenty of places to stay with in the Chicago area, with 5422 lodging choices including 2725 apartments. Why not relish this relaxing area's top-notch restaurants? Visit top sights in the region such as Wrigley Field and Michigan Avenue.
How do you know if an apartment is the right choice for your stay?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, and also for families wanting the conveniences of home.
What's the best apartment I should consider for a stay in Hillside?
Listed below are some of the more popular apartments in the area to choose from: Lakeview 2BR Apartment: Located 13.4 mi/21.6 km away in Chicago. Cozy, Fully Set-Up 1BR Space: It's located in Chicago, 13.9 mi/22.4 km away. Charming 2BR in Vibrant Lakeview: 12.7 mi/20.5 km away in Chicago. Huge Projector and Designated Workspace - Near Wrigley!: Located in Chicago, 11.2 mi/18.1 km from Hillside. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site.
What can I expect from the weather during my trip to Hillside?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Hillside. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Hillside are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What are the must-see places to visit in Hillside?
Hillside is known for its forests and shops. While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. You'll find favorite places to visit like Wrigley Field and Michigan Avenue in the larger area.
What's the best way to get to and around Hillside?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Chicago O'Hare Intl. Airport (ORD), which is located 6.9 mi (11 km) away from the city center. You can also search for flights into Chicago Midway Airport (MDW), which is 10.4 mi (16.7 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.