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Central Chicago, Illinois, United States of America

Central Chicago vacation rentals

We found 1,919 vacation rentals — enter your dates for availability

Discover a selection of 2,000 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 $133 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.
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Find spaces that suit your style

Condos/Apartments

View 1,611 Condos/Apartments

Houses

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Townhouses

View 25 Townhouses

Studios

View 1,376 Studios

Find the best place to stay — Central Chicago

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

Sleeps 4 · 1 Bedroom · 1 Bathroom
$262 avg/night
(354)

Superb 2BR Old Town APT, PRIME LOCATION!(+Parking)

Sleeps 7 · 2 Bedrooms · 1 Bathroom
$249 avg/night
(1)

💥⚡️Amazing Location | Luxury Apt | Rooftop Pool⚡️💥

Sleeps 5 · 1 Bedroom · 1 Bathroom
$133 avg/night

Sonder at Grant Park | Spacious One-Bedroom Apartment w/ City View

Sleeps 4 · 1 Bedroom · 1 Bathroom
$175 avg/night
(1)

52nd floor, VIEW, Pool, Balcony, Fitness Center, Grocery Store

Sleeps 4 · 1 Bedroom · 1 Bathroom
$223 avg/night
(17)

Best Location! Luxury 51st FL Amazing Views of Lake & City, Hotel-like Amenities

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$167 avg/night
(8)

Search 1,919 vacation rentals

Top rated rentals — Central Chicago
Stayed Dec 2021

Clean & Convenient in Chicago

Very conveniently located studio, short walk to Michigan Ave. The property has all things necessary for a couple. (Nice bedding, towels, some complimentary travel size hygiene products) The kitchen has all modern and well functioning appliances. The ...

SASHELLE H.
SASHELLE H.
Stayed Dec 2021

Excellent Property

Easy check in (there is a friendly attendant at the front desk 24/7), well stocked (finally, a rental apartment with salt, pepper, and a variety of other spices), and, of course, location and view is superb. We had one person in the bedroom and one o...

sandra l.
sandra l.
Stayed Dec 2021

Nice apartment downtown

Very clean apartment. Comfy beds. Only complaints are it was very warm for sleeping, even after turning the heat off and no availability to select A/C we could not get it to cool down. Also kitchen could be a bit better stocked. No starter coffee, bl...

karen M.
karen M.
Stayed Dec 2021

Great location - short walk to food and shopping

Great views of the lake, clean property, rooms are just a short walk off the elevators, and just a few steps to Michigan Ave. Property needs to upgrade the flat screen TV - poor audio and despite all my troubleshooting, picture never filled screen. :...

joe m.
joe m.
Stayed Dec 2021

Perfection!

The self check-in process is actually really easy to do. The unit itself was amazing and everything is walking distance! The apartment does get cold around the winter time just to keep in mind with that. The view from the top floor was amazing! We’ll...

Jorge B.
Jorge B.
Stayed Nov 2021

Thanksgiving 2021

Awesome communication from the beginning! Jim was a super host & answered so many questions very quickly. He made sure we even had last minute parking for my daughter. The location was perfect & the views were unbelievable! We had the most wonderful ...

Kim S.
Kim S.
Stayed Nov 2021

Great Location

Beautiful views from apartment! Walk to restaurants, shopping and grocery store next door. Washer and dryer in unit, blow dryer, shampoo, coffee maker, very well stocked. TV in the living room and bedroom. Direct TV does not get some sports channels ...

lourdes p.
lourdes p.
Stayed Nov 2021

Great stay at Grant Park

Fabulous location 10 stories above the SW edge of Grant Park, with a beautiful rounded corner window looking NE. Short walk from train; shopping and restaurants within steps; attentive host and great space with big, comfortable beds. A fabulous base ...

Bruce C.
Bruce C.

Lansing

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

Our 2022 property listings offer a large selection of 1,919 vacation rentals around Central Chicago. From 1,611 condo and apartment rentals to 280 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.