Central Chicago Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Central Chicago

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (987)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is HK$784
HK$1,149 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (627)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property – evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (386)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (376)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Business centre
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is HK$2,277
HK$2,674 total
includes taxes & fees
23 Nov - 24 Nov
Chicago luxury home suites
Terrace/patio
Chicago Luxury Penthouse Gold Coast Best Location

Condo in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"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."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is HK$483
HK$1,429 total
includes taxes & fees
3 Dec - 4 Dec
Twice as Nice: Chic 2BR Stay with Style & Space
Interior
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Holiday Home in Near North Side

9.4 out of 10, Exceptional, (104)
"Awesome space for our large group! Location couldn’t have been better - on a very nice street with tons of bars and restaurants near by."
United States
Elias P.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Terrace/patio
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Holiday Home in Downtown Chicago

10.0 out of 10, Exceptional, (24)
"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!"
United States
Erica S.
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Fridge, microwave, oven, stovetop
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Holiday Home in Downtown Chicago

10.0 out of 10, Exceptional, (6)
"We had a great stay! Inna provided us all the info we needed to check in smoothly when we arrived and the garage spot made it easy for us to park and unload luggage straight into the house. Everything was super clean! The house is big enough that even with so many guests everyone felt spread out and had their own space. We were able to take a 5ish min walk to the beach which was such a bonus! "
United States
Raleigh H.
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Dining
55-56 Mag Mile Penthouse

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (300)
"Location is fantastic and then there is the view ... spectacular!!! You lie in the bed and watch the night skyline of Chicago, unbeatable."
United States
Gert H.
55-56 Mag Mile Penthouse
Interior
Your Chicago get Away

Apartment in Downtown Chicago

8.4 out of 10, Very good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
The price is HK$1,696
HK$3,452 total
includes taxes & fees
24 Nov - 25 Nov
Your Chicago get Away
TV, stereo, offices
Luxury Loft Collection 703 - Terrace - River North

Apartment in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (20)
"Wonderful condo, incredible location. Would definitely stay again. "
United States
Durward H.
Luxury Loft Collection 703 - Terrace - River North
Indoor pool
Luxury Penthouse: Iconic Views + Exclusive Comfort

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (6)
"Very clean, nice views in a safe area and within walking distance of so many great attractions!"
United States
Gary
Luxury Penthouse: Iconic Views + Exclusive Comfort
Pool
Luxury 2BR on Michigan Ave with Private Balcony

Apartment in Downtown Chicago

9.8 out of 10, Exceptional, (16)
"Great place and attentive hosts. "
United States
Carol L.
Luxury 2BR on Michigan Ave with Private Balcony
TV, music library, stereo
River North's Rock N' Roll - In The Heart of the City

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (93)
"We had a great stay. Wonderful place & perfect location."
United States
Dana L.
River North's Rock N' Roll - In The Heart of the City
Smart TV
Spacious 2BR Group Stay near McCormick Place & Wintrust Arena

Holiday Home in Near South Side

8.0 out of 10, Very good, (2)
"Very clean, visually appealing space with plenty of room for our group. Check in and parking were straightforward and front desk staff were very helpful, though occasionally there won't be anyone at the front desk, making things a little confusing. Towels, toothbrushes, and little toothpastes were nearly stacked on the beds when we arrived which was a nice touch. Property is close to the train station as well as plenty of restaurants. Host was very responsive as well. Would recommend!"
United States
Simon H.
Spacious 2BR Group Stay near McCormick Place & Wintrust Arena
Terrace/patio
River North Private Deck With In and Out Parking

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is HK$1,868
HK$3,872 total
includes taxes & fees
3 Dec - 4 Dec
River North Private Deck With In and Out Parking
Fridge, microwave, oven, stovetop
Gorgeous 3BR River North Condo - Free Parking

Condo in Downtown Chicago

10.0 out of 10, Exceptional, (29)
"We had a great time in this beautiful condo. It is in a great location and we will be staying there again on our next trip to Chicago! "
United States
Rose W.
Gorgeous 3BR River North Condo - Free Parking
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"it was no balcony from our room, everything was great "
Janinka 2-night trip
Posted 10 hours ago
Eurostars Magnificent Mile

Find out more about Central Chicago

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