Central Chicago Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Central Chicago

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (957)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is HK$1,051
HK$1,462 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (561)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
Level Chicago – Old Town
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (688)
"great room, clean good space and close to places "
The price is HK$1,051
HK$1,233 total
includes taxes & fees
29 Oct - 30 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (363)
"An excellent place to stay in Chicago downtown."
Kasa South Loop Chicago
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
The price is HK$1,051
HK$1,233 total
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
Kasa River North Chicago
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (184)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
The price is HK$919
HK$1,078 total
includes taxes & fees
9 Nov - 10 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Property amenity
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
3.5 star property
7.6 out of 10, Good, (144)
"Very clean and affordable "
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Interior
Twice as Nice: Chic 2BR Stay with Style & Space
Twice as Nice: Chic 2BR Stay with Style & Space
9.4 out of 10, Exceptional, (9)
"Had a very nice time in Chicago!"
The price is HK$762
HK$1,745 total
includes taxes & fees
20 Oct - 21 Oct
Twice as Nice: Chic 2BR Stay with Style & Space
Terrace/patio
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
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
Interior
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (102)
"Everything was great for our stay! Inna very graciously came over and gave us a tour of the house, and some suggestions of things to check out in the city. The house was exactly as presented in the photos. It was clean and had everything we needed, it was really like a home away from home. We will definitely look to book this property again next time we come back to Chicago!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home
The One: A 1BR Stay That Feels Like Home
9.0 out of 10, Wonderful, (2)
"Very nice condo in a quiet neighborhood"
The price is HK$700
HK$1,585 total
includes taxes & fees
4 Nov - 5 Nov
The One: A 1BR Stay That Feels Like Home
Interior
Your Chicago get Away
Your Chicago get Away
8.4 out of 10, Very good, (6)
"Clean, fun space and responsive host! Loved the views from our room!"
The price is HK$1,855
HK$3,667 total
includes taxes & fees
23 Oct - 24 Oct
Your Chicago get Away
Terrace/patio
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
10.0 out of 10, Exceptional, (23)
"I cannot express how wonderful the stay was! From the communication level of the hosts to the details and cleanliness let alone the beauty of this home, it was absolutely wonderful in every way! We will absolutely be staying here again for any future needs!"
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Dining
55-56 Mag Mile Penthouse
55-56 Mag Mile Penthouse
10.0 out of 10, Exceptional, (298)
"Greta location, great stay, perfect location to so many things and if not subway at building for easy travel. "
55-56 Mag Mile Penthouse
Pool
Luxury 2BR on Michigan Ave with Private Balcony
Luxury 2BR on Michigan Ave with Private Balcony
9.8 out of 10, Exceptional, (16)
"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 "
Luxury 2BR on Michigan Ave with Private Balcony
TV, offices
Walk Everywhere! 5 mins to Magnificent Mile, River
Walk Everywhere! 5 mins to Magnificent Mile, River
7.8 out of 10, Good, (6)
"Excellent "
Walk Everywhere! 5 mins to Magnificent Mile, River
Property grounds
2nd Floor Flat in River North - 2S
2nd Floor Flat in River North - 2S
9.8 out of 10, Exceptional, (23)
"Great location and a very nice place"
2nd Floor Flat in River North - 2S
Indoor pool
Luxury Penthouse: Iconic Views + Exclusive Comfort
Luxury Penthouse: Iconic Views + Exclusive Comfort
10.0 out of 10, Exceptional, (5)
"Very clean, nice views in a safe area and within walking distance of so many great attractions!"
Luxury Penthouse: Iconic Views + Exclusive Comfort
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

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"Great room amazing vibe and amenities terrific gym! Full service 5 star hotel"
Mark 2-night trip
Posted 2 days ago
citizenM Chicago Downtown

Find out more about Central Chicago

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