Central Chicago Holiday Rentals

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Holiday Rentals in Central Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (649)
"Was very different and unique "
The price is HK$853
HK$1,229 total
includes taxes & fees
12 Jan - 13 Jan
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (348)
"Kasa was a pleasant surprise. Based on previous reviews, we understood that this was not a traditional hotel with amenities and had a virtual front desk but we did have an onsite person that did help us check in and store luggage. The apartment style room was very spacious and clean. We enjoyed having the extra space to spread out and the full kitchen was so handy when storing food or leftovers. Also, when we didn’t get utensils with our to go orders- Kasa had us covered. It was a nice home...
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (413)
"Beautiful Hotel with lots of amenities and entertainment in a walking distance "
The price is HK$787
HK$923 total
includes taxes & fees
30 Jan - 31 Jan
Sonder South Wabash

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (282)
"Besides hallways being loud and like frat house from 1 to 3am , the police showing up it was very great"
The price is HK$1,293
HK$1,691 total
includes taxes & fees
12 Jan - 13 Jan
Level Chicago – Old Town

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (180)
"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...
The price is HK$939
HK$1,102 total
includes taxes & fees
3 Feb - 4 Feb
Found Chicago powered by Sonder

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (251)
"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "
Kasa South Loop Chicago

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (115)
"Great"
The price is HK$732
HK$860 total
includes taxes & fees
15 Jan - 16 Jan
Kasa River North Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"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."
The price is HK$899
HK$1,055 total
includes taxes & fees
13 Jan - 14 Jan
Sonder Jewelers Row

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (87)
"Loved the location. "
The price is HK$804
HK$944 total
includes taxes & fees
9 Feb - 10 Feb
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is HK$917
HK$1,076 total
includes taxes & fees
9 Feb - 10 Feb
Sonder The Opal

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

10.0 out of 10, Exceptional, (215)
"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"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

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

10.0 out of 10, Exceptional, (283)
"Great penthouse with wonderful views of great Chicago architecture and the lake. I would stay again. Only minor issue was sleeping was more difficult than back home in small town Ohio. There were a lot of sirens etc. One bedroom also had a window open to the living room with all of its ambient light. Of course this issue is somewhat expected but I have not noticed noise as much staying at Chicago hotels. Still give it 5 stars"
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

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

9.4 out of 10, Exceptional, (83)
"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."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (52)
"Apartment was spacious. The 2 1/2 bathrooms were great to have for our group. Location was great for quick Uber to downtown area. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (29)
"We very much enjoyed our stay at this property! We were visiting Chicago for a fun weekend trip to celebrate our anniversary. The location was on a quiet street but within close walking distance to plenty of restaurants and shopping. The apartment was clean and very quiet in a beautiful, historic building. We highly recommend Tempo Cafe for breakfast. On our last morning in town, we actually saw Larry David, Jeff Garlin and Susie Essman at brunch there! "
Chic & Historic Apartment Steps from Mag Mile

Prime location Historic Chicago Townhouse

9.2 out of 10, Wonderful, (65)
"Always love coming here with family . Perfect location for playing in the city. Great space for togetherness and also time apart."
Prime location Historic Chicago Townhouse

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (18)
"I am an FCA advisor at a small rural school in Mid-Mo. We volunteer every year at the Operation Christmas Child facilities. I brought 6 high school students with me. The OCC facility is about 40 minutes from Chicago but we all wanted to experience the big city since we come from such a small rural area. The apartment was just as shown. We struggled with finding a parking spot as we drove a 10 passenger van but Dan does state that on the rental info there is no designated parking. We found...
Beautiful, Remodeled Penthouse Unit in Old Town!

Old-World, Classic Building Downtown

8.8 out of 10, Excellent, (13)
" 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"
Old-World, Classic Building Downtown

Brilliant Downtown Chicago 3-Bedroom Condominium

10.0 out of 10, Exceptional, (44)
"Apartment was as shown on Vrbo website - comfortable and clean. Good location, easy access and nearby parking. Kitchen well equipped, bathrooms modern and good towels and bed linens. Only modest issue is that the heating system is really quite loud when on. "
Brilliant Downtown Chicago 3-Bedroom Condominium

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

10.0 out of 10, Exceptional, (182)
"Great location! very comfortable!"
51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center
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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Other types of properties in Central Chicago you may be interested in

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8376)
"Loved the history of the hotel. accessible to everything"
The price is HK$722
HK$848 total
includes taxes & fees
10 Jan - 11 Jan
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3695)
"We had a good time "
The price is HK$747
HK$876 total
includes taxes & fees
16 Jan - 17 Jan
River Hotel

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very good, (3459)
"Every thing was great "
The price is HK$760
HK$893 total
includes taxes & fees
26 Jan - 27 Jan
Embassy Suites by Hilton Chicago Downtown River North
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.