Search Holiday Rentals in Chicago

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Top Holiday Rentals in Chicago

Sun-Drenched 1BR Apartment

The price is £182
includes taxes & fees
10 Jul - 11 Jul
Sun-Drenched 1BR Apartment

All Set Up - Furnished 1BR Unit

The price is £150
includes taxes & fees
7 Jul - 8 Jul
All Set Up - Furnished 1BR Unit

Stylish 1BR in West Loop

The price is £151
includes taxes & fees
6 Jul - 7 Jul
Stylish 1BR in West Loop

Luxury Unit with Rooftop Lounge & Spectacular City Views

The price is £141
includes taxes & fees
6 Jul - 7 Jul
Luxury Unit with Rooftop Lounge & Spectacular City Views

2 Connecting Suites at a 4⭐️ Hotel

The price is £513
includes taxes & fees
8 Jul - 9 Jul
2 Connecting Suites at a 4⭐️ Hotel

2 Connecting Suites at a 5⭐️ Hotel

The price is £2,710
includes taxes & fees
13 Jul - 14 Jul
2 Connecting Suites at a 5⭐️ Hotel

Cozy studio in Andersonville Chicago

9.8 out of 10, Exceptional, (8)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is £128
includes taxes & fees
7 Jul - 8 Jul
Cozy studio in Andersonville Chicago

Cozy Room with Rooftop Lounge & City Views in River North

The price is £163
includes taxes & fees
6 Jul - 7 Jul
Cozy Room with Rooftop Lounge & City Views in River North

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is £171
includes taxes & fees
6 Jul - 7 Jul
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

Modern Suite with Rooftop Lounge & Views of Downtown Chicago

The price is £196
includes taxes & fees
6 Jul - 7 Jul
Modern Suite with Rooftop Lounge & Views of Downtown Chicago

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

The price is £273
includes taxes & fees
6 Jul - 7 Jul
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

The price is £325
includes taxes & fees
6 Jul - 7 Jul
2 Relaxing Rooms with Rooftop Lounge & City Views of Chicago

2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The price is £345
includes taxes & fees
6 Jul - 7 Jul
2 Suites with Rooftop Lounge & Beautiful Views of Chicago Skyline

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (48)
"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"
The price is £254
includes taxes & fees
7 Jul - 8 Jul
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

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 £148
includes taxes & fees
9 Jul - 10 Jul
A quiet stay while you are away

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (56)
"Great trip "
The price is £150
includes taxes & fees
14 Jul - 15 Jul
Master qtr close to nature & easy urban facilities

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is £397
includes taxes & fees
6 Jul - 7 Jul
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

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 £138
includes taxes & fees
6 Jul - 7 Jul
Prime City Stay in a 1BR Apt

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is £230
includes taxes & fees
6 Jul - 7 Jul
Quaint Bungalow, near Great Lakes Naval Base

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 £124
includes taxes & fees
14 Jul - 15 Jul
Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton
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

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 entertainment choices. 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?

Stylish 3bd w/ backyard patio mins from Downtown! : This highly rated holiday home rental in Chicago offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Chicago is Your Next Vacation Home.

How many holiday rentals are there in Chicago?

With 1451 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 Art Institute of Chicago and CIBC Theatre, 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 Soldier Field.

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.