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

Central Chicago Holiday 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Central Chicago holiday rentals

A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (73 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is S$296
includes taxes & fees
4 Nov - 5 Nov
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,386 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is S$215
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
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, (545 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is S$391
includes taxes & fees
1 Nov - 2 Nov
Level Chicago – Old Town
A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (292 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
The price is S$284
includes taxes & fees
23 Nov - 24 Nov
The Gem Museum Suites
Terrace/patio

5. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
At Home in Oak Park
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.4 out of 10, Very good, (55 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is S$236
includes taxes & fees
25 Oct - 26 Oct
Wrigleyville Suites
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
Historic Oak Park Home
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is S$606
includes taxes & fees
4 Nov - 5 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A large brick house with a central chimney, a covered porch, and a brick pathway leading to the entrance.

9. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Lovely hotel in a great location, I stayed on the 23rd floor, the room was brilliant but the windows did not shield the sound of sirens all night!"
Stephen 5-night trip
Posted 2 hours ago
Eurostars Magnificent Mile

Explore a world of travel with Expedia