Central Chicago Holiday Rentals from €100: Search Short-Term Rentals

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Holiday Rentals in Central Chicago

"Staff is friendly and very helpful!"

includes taxes & fees

11 Dec - 12 Dec

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

"This property was in a good location - walked to Shedd Aquarium, Soldier Field, and good restaurants on South Michigan. Asked a few questions via text with prompt responses. No complaints with this clean property exactly as advertised."

includes taxes & fees

19 Dec - 20 Dec

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

"Very nice and spacious room. Comfortable bed. Great location. Very clean. Easy to check in/out."

"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"

includes taxes & fees

8 Dec - 9 Dec

"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...

includes taxes & fees

19 Dec - 20 Dec

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

"This was a great place and deserves the exceptional rating. The first night our oven didn’t work and they had it fixed first thing in the morning! All communication was quick and it had all we needed."

Free toiletries, hair dryer, towels, soap

"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"

includes taxes & fees

23 Dec - 24 Dec

"Had a great time and Kosa was awesome! Staff was excellent and the communication along the way was very organized."

includes taxes & fees

8 Dec - 9 Dec

"Perfect for a girls' weekend get-away. Close to CTA station and walkable to many attractions and restaurants. Comfortable and well-stocked with basic necessaries (dishes, cutlery, glassware). Added plus was the roof top terrace we enjoyed on the unseasonably balmy October evening! Our only complaint was not being able to stay longer. We hope to be back."

includes taxes & fees

23 Dec - 24 Dec

"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "

includes taxes & fees

11 Dec - 12 Dec

"Excited about our trip to Chicago and was not disappointed. Communication was very good from the homeowner location is perfect we had a fantastic time would recommend this for anyone wanting to enjoy downtown Chicago"

"This property worked well for our group of 14. The need to go outside to get between the upper and lower levels had been made very clear. It was a bit tricky at first with 5 young children, but we all adjusted pretty quickly. The lower level is more basic than upstairs but still worked very well for 5 of the group. The neighborhood was perfect for the location of the wedding we were attending, and having garage parking was fantastic. Definitely recommend."

"We had an amazing long weekend in Chicago! This place is amazing and we could not get over the views! The home was very clean and equipped with everything we needed. We would stay here again! Close to everything and lots within walking distance. "

"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "

"Very nice neighborhood, walking distance to Michigan Avenue, great food options, place has everything you need, I’ll stay there again, "

"It was great to stay in a beautiful grey stone in Gold Coast. Better yet it is located in an excellent area, less than 1/4 mile walking distance to the lake, around the corner from Michigan Avenue shopping, the Hancock Building, the Drake, Lou Malnati's and other great restaurants, and pharmacy-- we walked to all of these places! It felt like a home away from home with the layout of the home and nice neighborhood. It was stocked up with everything one needs in the kitchen, bathrooms, bedrooms...

"My friends since elementary spent 5 days at this darling condo. The place was clean and spacious. It was perfect for us 6 friends. The bedrooms were spacious, beds were comfortable and the sheets were perfect. I lived the soft pillows which made our sleep really comfortable. The kitchen was small but was perfect during our stay. It had the right amount of pots and pans available for our use although most of our meals were bought out. It also had baking pans that allowed us to make some fresh...

"So much fun! Dan was very communicative "

" This is 3 units in the same building, but on separate floors, and it is set up well. Did a great job in accomodating my large group, as part of a birthday weekend. Plenty of beds and great location 1 block from the lake. Property owner was responsive to messages and last-minute issues, and worth the rental. Jake"

"Great location! very comfortable!"

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"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled "

includes taxes & fees

8 Dec - 9 Dec

"The Hotel needs to get its iwn parking for sure it never stayed we had to walk 2 blocks that was terrible "

includes taxes & fees

11 Dec - 12 Dec

"I stayed for 3 nights with my wife and kid, everything was sweet and smooth, I arrived before the check in and they offered to take care of my luggage meanwhile the room was ready so I can go and start knowing the beauty of the city, the room was perfect for 3 or 4 persons, everything in order and clean, with all the things you need, perfectly located hotel, near the metro lines, the millennium park, the museum, the block 37, etc, etc and finally the check in and check out is effortless,...

includes taxes & fees

11 Dec - 12 Dec

Find out more about Central Chicago

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

Central Chicago holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Central 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 Central 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 Central Chicago holiday rentals we have selected for you start as low as €100 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Central Chicago rentals

At Expedia, we put the best Central 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 Central 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 Central 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 Central 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 Central Chicago properties

Club Quarters Hotel, Central Loop, Chicago

5/5 Excellent

"I stayed for 3 nights with my wife and kid, everything was sweet and smooth, I arrived before the check in and they offered to take care of my luggage meanwhile the room was ready so I can go and start knowing the beauty of the city, the room was perfect for 3 or 4 persons, everything in order and clean, with all the things you need, perfectly located hotel, near the metro lines, the millennium park, the museum, the block 37, etc, etc and finally the check in and check out is effortless, thanks, "

A verified traveller stayed at Club Quarters Hotel, Central Loop, Chicago

Posted 18 hours ago

5/5 Excellent

Favorite Chicago hotel.

"Absolutely wonderful hotel! Super friendly and helpful staff. Right on the Miracle Mile. Super close to train stops. Tons of restaurants and shops nearby. Completely safe area. Room had gorgeous views of downtown and evrn a small view of Lake Michigan. Will definitely stay here again next time I visit Chicago. "

A verified traveller stayed at Warwick Allerton - Chicago

Posted 3 days ago

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Holiday Rentals in Central Chicago

Check Central Chicago holiday rental availability

Holiday Rentals in Central Chicago

Sentral Michigan Avenue

Sonder South Wabash

Kasa Magnificent Mile Chicago

Level Chicago – Old Town

Found Chicago powered by Sonder

Kasa South Loop Chicago

Sonder Jewelers Row

Kasa River North Chicago

Sonder The Plymouth

Sonder The Opal

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Chic & Historic Apartment Steps from Mag Mile

Prime location Historic Chicago Townhouse

Brilliant Downtown Chicago 3-Bedroom Condominium

Beautiful, Remodeled Penthouse Unit in Old Town!

Old-World, Classic Building Downtown

51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

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Club Quarters Hotel, Central Loop, Chicago

Find out more about Central Chicago

Recent reviews of Central Chicago properties

Club Quarters Hotel, Central Loop, Chicago

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