Photo by Off The Beaten Track

Hillside Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Hillside

Stylish 4BR South Loop Home State 23-202

10.0 out of 10, Exceptional, (1)
"Very happy with stay. Good communication from property host. "
The price is AU$432
includes taxes & fees
5 Aug - 6 Aug
Stylish 4BR South Loop Home State 23-202

2 Connecting Suites at a 4⭐️ Hotel

The price is AU$1,147
includes taxes & fees
18 Aug - 19 Aug
2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

The price is AU$5,621
includes taxes & fees
10 Aug - 11 Aug
2 Connecting Suites at a 5⭐️ Hotel

“The Marlowe” A Couples Getaway

The price is AU$516
includes taxes & fees
20 July - 21 July
“The Marlowe” A Couples Getaway

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is AU$353
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 AU$404
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 AU$422
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 AU$484
includes taxes & fees
27 July - 28 July
Modern Suite with Rooftop Lounge & Views of Downtown Chicago

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

The price is AU$717
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 AU$824
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 AU$858
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 AU$967
includes taxes & fees
27 July - 28 July
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (7)
"Everything was as it was described. Very nice "
The price is AU$1,202
includes taxes & fees
5 Aug - 6 Aug
Walk to the Beach! Theater-Coffee Bar-Games-Gym

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 AU$416
includes taxes & fees
29 July - 30 July
Cozy 3-Bedroom Escape w/ Bonus Extra Living Area – Chicago Suburbs

Stylish 1BR in West Loop

The price is AU$314
includes taxes & fees
20 July - 21 July
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

The price is AU$450
includes taxes & fees
18 Aug - 19 Aug
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 AU$341
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 AU$319
includes taxes & fees
24 July - 25 July
Bright & Modern Lakeview Studio

Modern & Fully Furnished 1BR Apt

The price is AU$295
includes taxes & fees
24 July - 25 July
Modern & Fully Furnished 1BR Apt

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 AU$300
includes taxes & fees
28 July - 29 July
Comfy 2BR in Heart of Lakeview
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.
Save an average of 15% on thousands of hotels when you're signed in

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.