Central Chicago Vacation Rentals

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Vacation Rentals in Central Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Great stay. Will stay again!"
The price is ¥16,685
¥24,129 total
includes taxes & fees
Nov 25 - Nov 26
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"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."
The price is ¥18,895
¥22,182 total
includes taxes & fees
Dec 19 - Dec 20
Sonder South Wabash

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (332)
"Excellent stay. Excellent location. "
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is ¥27,172
¥34,527 total
includes taxes & fees
Nov 25 - Nov 26
Level Chicago – Old Town

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"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 ¥17,958
¥21,081 total
includes taxes & fees
Dec 18 - Dec 19
Found Chicago powered by Sonder

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very Good, (132)
"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!"
The price is ¥21,073
¥24,737 total
includes taxes & fees
Dec 16 - Dec 17
Sonder Jewelers Row

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is ¥13,847
¥16,256 total
includes taxes & fees
Dec 8 - Dec 9
Kasa River North Chicago

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very Good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is ¥17,600
¥20,660 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.4 out of 10, Very Good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is ¥19,558
¥22,958 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Opal

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

10.0 out of 10, Exceptional, (212)
"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

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

9.4 out of 10, Exceptional, (81)
"Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

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

10.0 out of 10, Exceptional, (278)
"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. "
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago

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, (26)
"Very nice neighborhood, walking distance to Michigan Avenue, great food options, place has everything you need, I’ll stay there again, "
Chic & Historic Apartment Steps from Mag Mile

Prime location Historic Chicago Townhouse

9.4 out of 10, Exceptional, (63)
"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...
Prime location Historic Chicago Townhouse

Brilliant Downtown Chicago 3-Bedroom Condominium

10.0 out of 10, Exceptional, (41)
"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...
Brilliant Downtown Chicago 3-Bedroom Condominium

Beautiful, Remodeled Penthouse Unit in Old Town!

9.2 out of 10, Wonderful, (17)
"So much fun! Dan was very communicative "
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

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, (8199)
"Loved it the view was amazing staff was super nice"
The price is ¥13,554
¥15,910 total
includes taxes & fees
Dec 8 - Dec 9
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3569)
"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."
The price is ¥14,999
¥17,607 total
includes taxes & fees
Dec 25 - Dec 26
River Hotel

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3297)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."
The price is ¥14,873
¥17,458 total
includes taxes & fees
Dec 24 - Dec 25
Club Quarters Hotel, Central Loop, Chicago
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.