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, (881)
"Great stay!"
The price is AU$304
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (338)
"A lot of good food options walkable distance. "
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (472)
"Great location and great property will stay again "
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (618)
"I would stay again. "
The price is AU$198
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (173)
"Great location!!!"
The price is AU$244
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$303
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (46)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is AU$229
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (163)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

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 AU$5,503
includes taxes & fees
1 Sept - 2 Sept
2 Connecting Suites at a 5⭐️ Hotel

Michigan Ave 2BR: Balcony, Exclusive Access

9.6 out of 10, Exceptional, (11)
"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

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

10.0 out of 10, Exceptional, (15)
"Very clean, kitchen stocked with all necessary items, and beds were extremely comfortable."
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

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

Your Chicago get Away

10.0 out of 10, Exceptional, (2)
"Clean, fun space and responsive host! Loved the views from our room!"
The price is AU$689
includes taxes & fees
25 Aug - 26 Aug
Your Chicago get Away

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (2)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (20)
"House was very accommodating and well stocked for a family of 4 including two teenage children. Check in was easy and as described, and location was easy walking distance to restaurants and shopping. Would definitely stay here again when in Chicago!"
Gorgeous 3BR River North Condo - Free Parking

2nd Floor Flat in River North - 2S

9.8 out of 10, Exceptional, (21)
"Beautiful space! Wonderful stay! Perfect location!"
2nd Floor Flat in River North - 2S

Modern 2b/2b family heaven with optional parking for up to 8 guests

9.2 out of 10, Wonderful, (5)
"Short walk to McCormick place. Would stay again."
Modern 2b/2b family heaven with optional parking for up to 8 guests
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