Des Plaines Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Des Plaines holiday rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (307 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
The price is AU$310
includes taxes & fees
19 Nov - 20 Nov
The Gem Museum Suites
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,409 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is AU$231
includes taxes & fees
6 Dec - 7 Dec
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is AU$330
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (49 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is AU$251
includes taxes & fees
10 Nov - 11 Nov
Wrigleyville Suites
A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

5. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (87 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is AU$350
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A two-story house with a brick exterior, a sloped roof, and a front porch.

6. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
The price is AU$501
includes taxes & fees
12 Nov - 13 Nov
At Home in Oak Park
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is AU$519
includes taxes & fees
16 Nov - 17 Nov
Historic Oak Park Home
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is AU$691
includes taxes & fees
10 Nov - 11 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

9. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
A building with a white exterior and a tree with white blossoms in front.

10. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is AU$700
includes taxes & fees
10 Nov - 11 Nov
Historic Oak Park Residence
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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Find holiday rentals that suit your style

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Top Des Plaines Hotel Reviews

A modern dining area with a large table, chairs, and a coffee station.
avid hotel Chicago O’Hare – Des Plaines by IHG

avid hotel Chicago O’Hare – Des Plaines by IHG

avid hotel Chicago O’Hare – Des Plaines by IHG
Des Plaines

10/10 Excellent

Great staff. Great service and great location
Australia
Clinton
Reviewed April 9, 2025
avid hotel Chicago O’Hare – Des Plaines by IHG

Find out more about Des Plaines

Everything you need to know about Des Plaines holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Des Plaines holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Des Plaines holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Des Plaines holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Des Plaines. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Des Plaines holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Des Plaines holiday rentals we have selected for you start as low as AU$109 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Des Plaines rentals

At Expedia, we put the best Des Plaines holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Des Plaines rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Des Plaines holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Des Plaines. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a holiday rental in Des Plaines?

Yes, there are holiday rentals close to the most popular sights in Des Plaines, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Des Plaines. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Des Plaines has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Des Plaines is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Des Plaines?

With 40 Expedia holiday rentals, you're guaranteed to find just the right place for your Des Plaines stay.

What can I see and do in Des Plaines?

Lake Park and Arndt Park are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places such as Wrigley Field and Navy Pier.

What are holiday rentals like in Des Plaines?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Des Plaines. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.