Chicago Holiday Rentals from NZ$158: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Chicago has to offer?

Clarendon Hills Top Floor : This highly rated holiday home rental in Chicago is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. 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. Other favourite homes for rent in Chicago are Lincoln Park Living - Suite 2! and Great 3 bedroom rental unit near Logan Square .

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Holiday Rentals in Chicago

"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."

includes taxes & fees

13 July - 14 July

Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and microwave.

includes taxes & fees

14 July - 15 July

Enjoy cooking in this kitchen with a gas stove, oven, and microwave, complemented by dark cabinetry.

includes taxes & fees

17 July - 18 July

includes taxes & fees

27 July - 28 July

Experience the grandeur of our lobby, featuring a central fountain, plush seating, and intricate woodwork.

includes taxes & fees

11 Aug - 12 Aug

Classic Chicago hotel with a symmetrical facade, large windows, and a central entrance.

includes taxes & fees

10 Aug - 11 Aug

Relax on the deck with four Adirondack chairs and a grill station.

"This was one of our favorite places we have ever stayed! It was clean, decorated beautifully, had comfortable beds, a refrigerator with an ice maker and filtered water, washer and dryer that worked great, a cool backyard with hammocks, and even little things like coffee creamer, toothpaste, and mouthwash in case you forgot yours. We stayed in three different rental places on our trip and this was by far our favorite! What a beautiful home! "

includes taxes & fees

14 July - 15 July

Kitchen features a gas stove, oven, and sink, with a colorful tile backsplash and window.

"Lovely little cottage in great location with excellent restaurants close by. Had everything we needed for our stay. Kitchen was perfectly equipped and having the washer dryer was such a bonus. The communication with the landlord was very good. Would absolutely stay here again. "

includes taxes & fees

27 July - 28 July

includes taxes & fees

27 July - 28 July

Stunning two-story building with a gabled roof and evenly spaced windows, set amidst a beautifully maintained lawn and garden.

"We stayed a few nights and everything was nice and clean. Thank you!"

includes taxes & fees

15 July - 16 July

includes taxes & fees

27 July - 28 July

Enjoy meals in this dining room with a large table and six chairs, a vase with flowers, and a comfortable rug.

"Great experience, lots of cooking materials "

includes taxes & fees

10 Aug - 11 Aug

includes taxes & fees

27 July - 28 July

Fridge, oven, stovetop, coffee/tea maker

"The area is quiet and the apartment is close to a dog park which is open to non-residents. There is a paved walkway right by the park that’s nice so I was able to walk my dog in the morning. The property manager immediately replied to any questions I had and the apartment was fully stocked in the kitchen, etc. I booked this because of the cost. I was in town to see the Indiana Dunes. I would stay here again."

includes taxes & fees

8 Aug - 9 Aug

includes taxes & fees

27 July - 28 July

1 bedroom, iron/ironing board, travel cot, WiFi

"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."

includes taxes & fees

14 July - 15 July

includes taxes & fees

27 July - 28 July

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Find out more about Chicago

Everything you need to know about Chicago 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 Chicago 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 Chicago holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chicago holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chicago. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chicago 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 Chicago holiday rentals we have selected for you start as low as NZ$158 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chicago rentals

At Expedia, we put the best Chicago 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 Chicago 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 Chicago 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 Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Chicago properties

5/5 Excellent

"Our room was clean and comfortable. Staff was very friendly and helpful. Would stay here again! "

A verified traveller stayed at Hilton Chicago/Magnificent Mile Suites

Posted 6 hours ago

Hilton Garden Inn Chicago Downtown/Magnificent Mile

5/5 Excellent

"This hotel is in a perfect location. Went to Chicago to watch baseball at Wrigley & Rate Field. The red line train is steps from the hotel entrance and takes you to both ball parks within 15-20 minutes. The hotel is a few blocks from the river walk and surrounded by restaurant options. Only knock was the noise at night with constant sirens going off which is outside of the hotels control. Pack some ear plugs and you will love the location of this hotel. "

A verified traveller stayed at Hilton Garden Inn Chicago Downtown/Magnificent Mile

Posted 12 hours ago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

5/5 Excellent

"Loved this property and location! Walking distance to the pier, magnificent mile, and the center of town! Free breakfast and evening cocktails were a definite perk!!"

A verified traveller stayed at Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Posted 2 days ago

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Frequently asked questions

Can I find holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed art scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

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

Clarendon Hills Top Floor: This highly rated holiday home rental in Chicago is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. 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. Other favourite homes for rent in Chicago are Lincoln Park Living - Suite 2! and Great 3 bedroom rental unit near Logan Square.

How many holiday rentals are there in Chicago?

With 1463 Expedia holiday rentals, you're guaranteed to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Michigan Avenue and Navy Pier.

What are holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

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Chicago Holiday Rentals

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Holiday Rentals in Chicago

All Set Up - Furnished 1BR Unit

Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Luxury Unit with Rooftop Lounge & Spectacular City Views

2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

Cozy house in the city

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Cozy Room with Rooftop Lounge & City Views in River North

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

A quiet stay while you are away

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

Quaint Bungalow, near Great Lakes Naval Base

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

Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

Prime City Stay in a 1BR Apt

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

Find out more about Chicago

Recent reviews of Chicago properties

Hilton Chicago/Magnificent Mile Suites

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Embassy Suites by Hilton Chicago Downtown River North

Crowne Plaza Chicago West Loop by IHG

Hotel Felix River North/Magnificent Mile

The Wade

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

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