List your Property
Central Chicago, Illinois, United States of America

Central Chicago vacation rentals

We found 1,378 vacation rentals — enter your dates for availability

Discover a selection of 1,500 vacation rentals in Central Chicago, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $207 per night, and condos and houses are popular options for a stay in Central Chicago. Either way, you'll find a rental for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style

Condos/Apartments

View 1,080 Condos/Apartments

Houses

View 205 Houses

Townhouses

View 19 Townhouses

Studios

View 991 Studios

Find the best place to stay — Central Chicago

55/56th Floor Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
$515 avg/night
(208)

52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi

Sleeps 4 · 1 Bedroom · 1 Bathroom
$229 avg/night
(330)

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 Bedroom · 1 Bathroom
$237 avg/night
(119)

53/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony

Sleeps 8 · 2 Bedrooms · 3 Bathrooms
$461 avg/night
(127)

51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

Sleeps 7 · 2 Bedrooms · 2 Bathrooms
$619 avg/night
(118)

BEST LOCATION!! LUX 2b/2b Condo, 51st Floor AMAZING Views, Great Amenities!

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$207 avg/night
(17)

Search 1,378 vacation rentals

AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many vacation rentals are available around Central Chicago, US?

Our 2021 property listings offer a large selection of 1,378 vacation rentals around Central Chicago. From 1,080 condo and apartment rentals to 205 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.