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, (841)
"We would stay here again. Very happy with our stay "
The price is NZ$413
includes taxes & fees
17 Aug - 18 Aug
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (331)
"Hotel was nice"
The price is NZ$597
includes taxes & fees
19 Aug - 20 Aug
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (447)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (584)
"Great place and location. "
The price is NZ$357
includes taxes & fees
21 Aug - 22 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (121)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is NZ$274
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (320)
"I definitely enjoyed my stay and roof deck was the highlight. "
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is NZ$314
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (156)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is NZ$314
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

Michigan Ave 2BR: Balcony, Exclusive Access

10.0 out of 10, Exceptional, (10)
"Roomy 2 bedroom with great hideaway beds.Excellent location easy to get everywhere. Super responsive hosts Nice building with gym and parking option for visitors "
Michigan Ave 2BR: Balcony, Exclusive Access

Walk Everywhere! 5 mins to Magnificent Mile, River

10.0 out of 10, Exceptional, (1)
"Loved the location. Clean and any concerns were addressed timely. "
Walk Everywhere! 5 mins to Magnificent Mile, River

Studio flat in the heart of Chicago's Gold Coast

9.6 out of 10, Exceptional, (10)
"The property is in downtown and very close to everything "
Studio flat in the heart of Chicago's Gold Coast

2 Connecting Suites at a 5⭐️ Hotel

The price is NZ$6,049
includes taxes & fees
10 Aug - 11 Aug
2 Connecting Suites at a 5⭐️ Hotel

2nd Floor Flat in River North - 2S

9.8 out of 10, Exceptional, (21)
"Easy to get around the city."
2nd Floor Flat in River North - 2S

McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6

9.0 out of 10, Wonderful, (2)
"Overall stay, I would rate a 4.2 out of 5. The host was very responsive. The only problems I did encounter was parking, the inconsistency of the thermostat, and beds. Overall I would book again. So that should say a lot. "
McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6

Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

10.0 out of 10, Exceptional, (12)
"Very clean, kitchen stocked with all necessary items, and beds were extremely comfortable."
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

Historic and Unique Brownstone in Gold Coast - 3

10.0 out of 10, Exceptional, (3)
"My mother and I had a few days in the city, going shopping and enjoying restaurants. This place was a lovely historic property in a convenient location. Very clean and comfortable!"
Historic and Unique Brownstone in Gold Coast - 3

Luxury Downtown Penthouse with Private Rooftop!

9.0 out of 10, Wonderful, (19)
"Overall very happy with our stay"
Luxury Downtown Penthouse with Private Rooftop!

BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)

9.4 out of 10, Exceptional, (16)
"Large and spacious shared space and living room, lots of amenities like blankets, pillows, and towels. Comfortable beds and many beds and couches. AC in every room. Fantastic place to stay"
BIG Downtown Penthouse|Vintage 3bd (GYM+Balcony)

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (1)
"This property is the perfect luxe option for a stay in Chicago! Our family came into town for our daughter’s graduation and the property was absolutely perfect for our family to stay and celebrate. It is nestled optimally in the Gold Coast neighborhood on the top of Magnificent Mile and a very short walk to the water. The home is perfectly appointed with all that you need and want for your stay. It is designed to allow plenty of gorgeous natural light in, with top quality linens and many...
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
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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Top Central Chicago Hotel Reviews