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, (442)
"We stayed overnight after attending a concert at Northerly Island. It was a convenient walk there and back. We also had a beautiful view of Navy Pier. The room was clean, as was the property itself. The staff and residents were friendly. I would stay again and also recommend to anyone thinking about it."
The price is ¥25,304
¥34,315 total
includes taxes & fees
Jun 17 - Jun 18
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (314)
"Comfortable to stay"
The price is ¥25,110
¥29,479 total
includes taxes & fees
Jul 2 - Jul 3
Sonder South Wabash
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (257)
"Very comfortable accommodations and good amenities and location. "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (216)
"Great room - fabulous fitness center. Easy access to grocery stores to stock fridge. Room is furnished with all amenities. "
The price is ¥42,239
¥52,257 total
includes taxes & fees
Jun 18 - Jun 19
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (135)
"I loved my stay at Found Chicago! The logistical communication was easy to understand and implement, and I liked that it was contactless. It was nice to use my PIN code for room entrance instead of keeping track of a key. The WiFi was sufficient for remote meetings on my laptop. And all of the amenities (lobby access, luggage locker, and printer) were convenient and easy to use. I highly recommend this hotel, and I'll plan to stay here again. "
The price is ¥18,203
¥21,370 total
includes taxes & fees
Jul 14 - Jul 15
Found Chicago powered by Sonder
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (68)
"Room was great! Spacious, clean and perfect for a night or longer stay. View was also very nice!"
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (111)
"Loved it "
The price is ¥28,392
¥33,332 total
includes taxes & fees
Jul 7 - Jul 8
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, (164)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, (68)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ¥22,209
¥26,073 total
includes taxes & fees
Jul 15 - Jul 16
Sonder The Plymouth
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (200)
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.2 out of 10, Very Good, (15)
"I like that was contactless and easy to access. "
The price is ¥32,671
¥38,356 total
includes taxes & fees
Jul 1 - Jul 2
Sonder The Opal
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is ¥25,814
¥33,926 total
includes taxes & fees
Jul 3 - Jul 4
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
9.4 out of 10, Exceptional, (3)
"Easy check in, staff on property were so nice. Property has a lap pool and a gym. Location was great and price was very comfortable."
The price is ¥29,843
¥38,648 total
includes taxes & fees
Jun 30 - Jul 1
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
Million Dollar Views! Luxury Downtown Skyhouse!
10.0 out of 10, Exceptional, (95)
"Properly was clean and had everything we needed. Our visit went by quickly. Location was close to restaurants and grocery store. We recommend staying here."
The price is ¥86,074
¥182,242 total
includes taxes & fees
Jun 18 - Jun 19
Million Dollar Views! Luxury Downtown Skyhouse!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.0 out of 10, Wonderful, (8)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Stay in the Heart of the City! Complimentary Bicycles for exploring!
10.0 out of 10, Exceptional, (2)
"Enjoyed the walkability of this location to all downtown Chicago has to offer. The onsite amenities were also wonderful"
The price is ¥32,042
¥42,016 total
includes taxes & fees
Jun 16 - Jun 17
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (72)
"Stayed with 10 friends for the weekend. Clean unit with plenty of beds. Listing and pictures are accurate. Great location close to bars, restaurants, and train stop. Property manager was very responsive. Very easy check-in/check-out."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.0 out of 10, Wonderful, (44)
"Communication was fantastic. Location is excellent. I stayed there with my wife and kids and there was plenty of room. Would be great for a big group of friends or a bachelor party weekend."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (4)
"The unit was a great size for our 7-person group trip to Chicago. We’ll appointed with pulsated hardware and decor. Super close to transit made getting to Wrigley, Navy Pier, Downtown, and the zoo extremely easy. Rooftop was a amazing and Dan was responsive and made the check in/out process a breeze."
Breathtaking Downtown Penthouse B - Sleeps 11
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
10.0 out of 10, Exceptional, (267)
"Great stay. The owners are very communicative. We checked in easily with the door staff. We arrived early and the door staff was helpful and allowed us to store our bags and explore the area. The inside matches the pictures. The outside has to been seen day or night to appreciate the pictures. Beds are very comfortable. Kitchen is well appointed. (A grocery store is ten steps away from downstairs entry.) the bathrooms were clean. The washer and drier are very useful. It is a two story unit....
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
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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.

Other types of properties in Central Chicago you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6958)
"Great values. "
The price is ¥23,393
¥27,467 total
includes taxes & fees
Jun 18 - Jun 19
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, (2382)
"I love the location of this hotel. It’s vey convenient to walk everywhere. Breakfast is awesome. Front desk is lukewarm not the friendliest but not the worse. One is not even paying attention and charged me again even though I prepaid my stayed in Expedia. It’s still showing pending in my CC so I’m hoping it will get dropped off to avoid the hassle of disputing the transaction. I stayed in Embassy in DC before and the front desk were extra nice and they gave us voucher because I was a gold...
The price is ¥32,334
¥37,959 total
includes taxes & fees
Jun 17 - Jun 18
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2952)
"Perfect place with a water view. Walkable "
The price is ¥25,569
¥30,019 total
includes taxes & fees
Jul 3 - Jul 4
River Hotel
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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