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, (867)
"Great stay!"
The price is AU$349
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (337)
"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, (461)
"Kasa apartments are two blocks away from Magnificent mile street. It is a really nice area and there are a lot of attractions close by. We had a wonderful time!!"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (607)
"I would stay again. "
The price is AU$257
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (326)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (129)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$304
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (171)
"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 AU$274
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (160)
"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, (44)
"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$243
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

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

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

10.0 out of 10, Exceptional, (14)
"Very clean, kitchen stocked with all necessary items, and beds were extremely comfortable."
Skyline Serenity: Sauna, Hot Tub, Peloton, Views, Free Parking, Wifi

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

2 Connecting Suites at a 5⭐️ Hotel

The price is AU$5,885
includes taxes & fees
22 Aug - 23 Aug
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

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

River North Private Deck With In and Out Parking

10.0 out of 10, Exceptional, (1)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
River North Private Deck With In and Out Parking

Historic and Unique Brownstone in Gold Coast - 3

9.0 out of 10, Wonderful, (4)
"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!

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

Luxury Loft Collection 703 - Terrace - River North

2.0 star property
10.0 out of 10, Exceptional, (16)
"Very attentive hosts. Will definitely stay here again. Fantastic location, upscale in every way!"
Luxury Loft Collection 703 - Terrace - 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.
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Top Central Chicago Hotel Reviews