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Hillside Holiday Rentals

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Holiday Rentals in Hillside

2 Connecting Suites at a 4⭐️ Hotel

The price is NZ$1,231
includes taxes & fees
18 Aug - 19 Aug
2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

The price is NZ$6,219
includes taxes & fees
3 Aug - 4 Aug
2 Connecting Suites at a 5⭐️ Hotel

“The Marlowe” A Couples Getaway

The price is NZ$551
includes taxes & fees
28 July - 29 July
“The Marlowe” A Couples Getaway

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is NZ$364
includes taxes & fees
27 July - 28 July
Luxury Unit with Rooftop Lounge & Spectacular City Views

Cozy Room with Rooftop Lounge & City Views in River North

The price is NZ$417
includes taxes & fees
27 July - 28 July
Cozy Room with Rooftop Lounge & City Views in River North

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is NZ$433
includes taxes & fees
27 July - 28 July
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is NZ$558
includes taxes & fees
10 Aug - 11 Aug
Modern Suite with Rooftop Lounge & Views of Downtown Chicago

2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

The price is NZ$722
includes taxes & fees
27 July - 28 July
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

The price is NZ$849
includes taxes & fees
27 July - 28 July
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The price is NZ$890
includes taxes & fees
27 July - 28 July
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is NZ$922
includes taxes & fees
27 July - 28 July
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

Cozy 3-Bedroom Escape w/ Bonus Extra Living Area – Chicago Suburbs

10.0 out of 10, Exceptional, (2)
"Lakeia was very accommodating throughout our stay."
The price is NZ$449
includes taxes & fees
5 Aug - 6 Aug
Cozy 3-Bedroom Escape w/ Bonus Extra Living Area – Chicago Suburbs

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (1)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is NZ$357
includes taxes & fees
28 July - 29 July
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

The price is NZ$352
includes taxes & fees
28 July - 29 July
Sun-Drenched 1BR Apartment

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 NZ$332
includes taxes & fees
24 July - 25 July
The One: A 1BR Stay That Feels Like Home

Bright & Modern Lakeview Studio

8.0 out of 10, Very good, (1)
"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 NZ$341
includes taxes & fees
24 July - 25 July
Bright & Modern Lakeview Studio

Comfy 2BR in Heart of Lakeview

8.0 out of 10, Very good, (1)
"The location is very convenient—just a 15-minute walk from Boystown and 6 minutes from some great breakfast spots. One mattress should be replaced, as it is quite worn. Everything else was fine. I'm not a big fan of noisy window AC units, especially since I’m a light sleeper; even with earplugs, the noise was still bothersome. The lockbox for the key is a bit tricky—I imagine others might find it difficult to open as well. Overall, the place was more affordable than other options, so I’d give...
The price is NZ$321
includes taxes & fees
24 July - 25 July
Comfy 2BR in Heart of Lakeview

Sleek Style 3BR Haven - Free Parking - Ashland 2N

9.4 out of 10, Exceptional, (3)
"Centrally located "
The price is NZ$400
includes taxes & fees
5 Aug - 6 Aug
Sleek Style 3BR Haven - Free Parking - Ashland 2N

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (13)
"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 NZ$294
includes taxes & fees
11 Aug - 12 Aug
Cozy studio in Andersonville Chicago

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (2)
"Everything was as described, clean and enjoyable, had everything you might need. Its not the biggest studio, but they did a good job with the space. Its great for the price. "
The price is NZ$315
includes taxes & fees
11 Aug - 12 Aug
Relaxing Chicago Studio
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 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 are some of the best holiday rentals that Hillside has to offer?

4BR Retreat w/ Theater, Game Room & Backyard: This holiday home rental outside of Hillside offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 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.