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Central Chicago Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Central Chicago vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1020)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is P6,940
P9,870 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is P7,929
P9,308 total
includes taxes & fees
Dec 28 - Dec 29
Chicago luxury home suites
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (405)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Business center
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Private kitchen
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is P20,708
P36,674 total
includes taxes & fees
Dec 30 - Dec 31
ENVITAE Hotel 4 Bedroom Luxury Apartments
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

Swissotel - Chicago

Swissotel - Chicago

10/10 Excellent
"Super good location and with amazing views. Also the staff is friendly and made me feel welcomed everyday of my stay. Big shout out to the manager Simona"
Karla 4-night trip
Posted 1 day ago
Swissotel - Chicago

Find out more about Central Chicago

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Look no further and take a look at our great range of rental properties in Central Chicago!