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

Central Chicago Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Central Chicago vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,390 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is NT$4,666
NT$5,478 total
includes taxes & fees
Nov 22 - Nov 23
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (76 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
The price is NT$5,247
NT$8,175 total
includes taxes & fees
Nov 4 - Nov 5
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (551 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NT$5,983
NT$7,827 total
includes taxes & fees
Nov 11 - Nov 12
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Central Chicago Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Hotel was nice. Just need more elevators"
Dyleescha 3-night trip
Posted less than an hour ago
The Wade

Find out more about Central Chicago

Search for holiday rentals in Central Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Central Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Central Chicago
  • Use the map to find apartments and other holiday homes in the Central Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Central Chicago while they last

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

Explore a world of travel with Expedia