Chicago Holiday Rentals : Search Short-Term Rentals

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

Luxury Home Away From Your Home : 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 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Chicago are Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars and Eddy House, Roscoe Village Hideaway .

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Holiday Rentals in Chicago

"Sandra and Joy are welcoming and helpful. Great front desk."

includes taxes & fees

4 Feb - 5 Feb

"Enjoyed My Stay."

includes taxes & fees

24 Feb - 25 Feb

Superior Apartment, 1 Bedroom, Balcony, City View | Living area

"Ótima localização e estadia bastante segura e confortável. Faltam alguns itens na cozinha, mas nada que afeta negativamente. "

includes taxes & fees

26 Feb - 27 Feb

"Soooo close to Union Station and next door to a classic breakfast restaurant that has been around for decades, Lou Mitchell’s (closed Mon & Tue tho). Easy self check in, great quick customer service, comfortable bed and bedding, quiet except for the occasional ambulance. I reserved the Queen studio and the kitchenette was perfect. I’d stay there again on my next trip. "

includes taxes & fees

4 Feb - 5 Feb

"Amazing stay ! Love this property every time I’m in Chicago. "

includes taxes & fees

9 Feb - 10 Feb

"It was a Great option, straight and contactless."

includes taxes & fees

24 Feb - 25 Feb

49-inch Smart TV with digital channels, TV, streaming services

"Very walkable area! The building is older but was pretty clean."

50-inch Smart TV with satellite channels

"This was so comfortable, clean and very quiet. Having no front desk was concerning but it didn't really matter. The response to any concern was addressed quickly and professionally. I love this place. "

Free toiletries, hair dryer, towels, soap

"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."

includes taxes & fees

26 Feb - 27 Feb

42-inch Smart TV with digital channels, TV, streaming services

"The view from our apartment was breathtaking! The apartment was very clean and very nice. Easy access and the neighborhood was very nice. My husband and I had an amazing time in Chicago and we are definitely returning to this location in our future stay. "

"Our stay was amazing. "

includes taxes & fees

4 Feb - 5 Feb

"Great apartment, we were given an extra bedroom which we used as a wardrobe. Well equipped, modern and well decorated. Full cooker, fridge freezer, microwave. We were provided with tablets for laundry and dishwasher. Washing up.liquids, towels and toilet roll. Great shower. Loved the location. We enjoy cities and walking. Trains a very short walks (several L stations). Target was a 15 minute walk, great independent coffee shop 2 mins from entrance. We will use Sonder again. "

includes taxes & fees

5 Feb - 6 Feb

"Very nice 1-bedroom apartment with a very comfortable king-size bed. A 2-minute walk from the subway station and a lot of tourist places are a walkable distance too. Communication was great and very easy via text message. We loved our stay :-) "

includes taxes & fees

3 Feb - 4 Feb

40-inch flat-screen TV with digital channels, TV

"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "

includes taxes & fees

26 Feb - 27 Feb

"All conditions (like the deposit) should be clear in the description. This is not a hotel or a hotel, it's a private place. All this should be clear at the moment of reservation. The property was good enough but the communication with the host was troublesome. And the price is not that low. I will look for a hotel next time. "

includes taxes & fees

4 Feb - 5 Feb

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

"We had a great stay in this Evanston lower level studio apartment while in town for our reunion and Homecoming weekend at Northwestern. The studio is clean, nicely decorated, good amenities, and conveniently located to both the NU campus and downtown Chicago. Having a dedicated parking spot was awesome too, as the off-street parking fills up quickly in the evening. My only recommendation would be replacing the really firm mattress with a softer one, or a memory foam topper. All in all we had...

includes taxes & fees

5 Feb - 6 Feb

"We stayed 5 days beginning Christmas Day and it was one of the most memorable vacations we’ve taken as a family. Our hosts were perfect in that they were always quick to respond (1-2 minutes), but everything was so well planned that we never really needed anything. The patio balcony is HUGE and you can see everything from 55 stories. Great views of the lake. Easy access to all of downtown via Uber or a short walk. We can’t say enough about this apartment, and we’d love to stay there again. ...

includes taxes & fees

11 Feb - 12 Feb

"A clean, spacious, affordable option in a perfect location in Lincoln Park. Plan to return in the future."

"We had a group of couples coming to Chicago from different locations, and this was the perfect spot for us to be all together, but also have our own rooms and spaces. Everything was easy, and when we had a question on parking when we arrived later in the evening, John was very prompt in responding and helping us right away. "

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Other types of properties in Chicago you may be interested in

"The staff was wonderful and accommodating. I had high hopes that since i had booked the rooms several months in advanced that they would have been together, but I'm sure that is not something that can be helped. I had a wonderful stay and that is what mattered the most. "

includes taxes & fees

3 Feb - 4 Feb

"Best hotel stay I've ever had! Great price, great service. The river view was amazing. "

includes taxes & fees

3 Feb - 4 Feb

"A very good experience. The vibes was immaculate. "

includes taxes & fees

5 Feb - 6 Feb

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, apart-hotels, 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 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.

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Recommended Holiday Rental Destinations

Frequently asked questions

Can I find holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Field Museum of Natural History, 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?

Luxury Home Away From Your Home: 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 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Chicago are Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars and Eddy House, Roscoe Village Hideaway.

How many holiday rentals are there in Chicago?

With 1291 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 Maggie Daley 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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Holiday Rentals in Chicago

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Holiday Rentals in Chicago

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