Chicago Holiday Rentals

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Holiday Rentals in Chicago

All Set Up - Furnished 1BR Unit

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
13 July - 14 July
All Set Up - Furnished 1BR Unit

Stylish 1BR in West Loop

The price is NZ$334
includes taxes & fees
14 July - 15 July
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

The price is NZ$455
includes taxes & fees
17 July - 18 July
Sun-Drenched 1BR Apartment

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is NZ$395
includes taxes & fees
27 July - 28 July
Luxury Unit with Rooftop Lounge & Spectacular City Views

2 Connecting Suites at a 4⭐️ Hotel

The price is NZ$1,307
includes taxes & fees
11 Aug - 12 Aug
2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

The price is NZ$6,033
includes taxes & fees
10 Aug - 11 Aug
2 Connecting Suites at a 5⭐️ Hotel

Cozy house in the city

2.0 star property
10.0 out of 10, Exceptional, (2)
"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! "
The price is NZ$621
includes taxes & fees
14 July - 15 July
Cozy house in the city

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

2.0 star property
9.6 out of 10, Exceptional, (9)
"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. "
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Cozy Room with Rooftop Lounge & City Views in River North

The price is NZ$434
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$454
includes taxes & fees
27 July - 28 July
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

A quiet stay while you are away

9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
The price is NZ$311
includes taxes & fees
15 July - 16 July
A quiet stay while you are away

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is NZ$535
includes taxes & fees
27 July - 28 July
Modern Suite with Rooftop Lounge & Views of Downtown Chicago

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is NZ$520
includes taxes & fees
10 Aug - 11 Aug
Quaint Bungalow, near Great Lakes Naval Base

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

The price is NZ$802
includes taxes & fees
27 July - 28 July
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

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

10.0 out of 10, Exceptional, (2)
"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."
The price is NZ$338
includes taxes & fees
8 Aug - 9 Aug
Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

The price is NZ$885
includes taxes & fees
27 July - 28 July
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

Prime City Stay in a 1BR Apt

9.0 out of 10, Wonderful, (2)
"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."
The price is NZ$302
includes taxes & fees
14 July - 15 July
Prime City Stay in a 1BR Apt

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The price is NZ$922
includes taxes & fees
27 July - 28 July
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline
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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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.