A city skyline at dusk with illuminated buildings reflecting on the water.

Central Chicago Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Central Chicago holiday rentals

Lake

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (26 reviews)
"Great location and super clean!"
United States
Erica
The price is S$327
includes taxes & fees
9 Sept - 10 Sept
Kasa Lake Shore Chicago
Exterior

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,306 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is S$263
includes taxes & fees
9 Sept - 10 Sept
Sentral Michigan Avenue
Private kitchen

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (523 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is S$465
includes taxes & fees
9 Sept - 10 Sept
Level Chicago – Old Town
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"excelente y muy cuidado"
Madeleine 3-night trip
Posted less than an hour ago
Congress Plaza Hotel

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