Photo by Phil Ostroff

Central Chicago holiday rentals

We found 2,912 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Central Chicago

Showing deals for:13 Nov - 20 Nov

Private kitchen
Terrace/patio
Interior
Living area
Wonderful
(12 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$11,737
for 7 nights, 1 apartment
AU$1,677 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
The building
River North Luxury Living
Outdoors at night
Interior
Exceptional
(104 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$4,571
for 7 nights, 1 apartment
AU$653 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Dining
Interior
Living area
Private kitchen
Exceptional
(35 reviews)

Lux Home in Chicago 7mins Downtown

Chicago

7% off
AU$6,588
for 7 nights, 1 home
AU$941 per night
includes taxes & fees
Lux Home in Chicago 7mins Downtown
Outdoor dining
Private kitchen
Living area
Room
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

7% off
AU$3,363
for 7 nights, 1 home
AU$480 per night
includes taxes & fees
Private Historic Coach House Wicker Park
6 steps to enter the unit.
Interior
Private kitchen
Interior
Exceptional
(19 reviews)

Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park

Chicago

7% off
AU$2,968
for 7 nights, 1 home
AU$424 per night
includes taxes & fees
Lofty Garden Retreat Artist-Music Friendly 2BR in Humboldt Park
Dining
Private kitchen
Bedroom 1
Living area
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
AU$6,686
for 7 nights, 1 home
AU$955 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Room
Interior
Dining
Private kitchen
Exceptional
(39 reviews)

Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP

Berwyn

8% off
AU$1,825
for 7 nights, 1 apartment
AU$261 per night
includes taxes & fees
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Kitchen
Living Room
Bedroom 1 (King Size) + 55Inch TV
Front Yard View
Exceptional
(21 reviews)

Spacious 5 BR / King Size Beds + Private Parking!

Chicago

8% off
AU$6,618
for 7 nights, 1 home
AU$945 per night
includes taxes & fees
Spacious 5 BR / King Size Beds + Private Parking!
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area
Dining room area
Exceptional
(96 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,332
for 7 nights, 1 home
AU$905 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Private kitchen
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Convenient on-premis laundry room with coin operated washer and dryer
Bedroom #1 w 2 full size beds plus a desk
Wonderful
(20 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,691
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Terrace/patio
Living area
Living area
Dining
Exceptional
(55 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$3,686
for 7 nights, 1 apartment
AU$527 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Room
Living area
Miscellaneous
Private kitchen
Exceptional
(12 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,861
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Room
Interior
Private kitchen
Interior
Exceptional
(13 reviews)

Modern + Cozy Chicago stay w/garage parking & 20min to downtown

Chicago

7% off
AU$1,775
for 7 nights, 1 apartment
AU$254 per night
includes taxes & fees
Modern + Cozy Chicago stay w/garage parking & 20min to downtown
Living area
Interior
Room
Interior
Exceptional
(11 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,979
for 7 nights, 1 apartment
AU$426 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior
Living area
Private kitchen
Room
Exceptional
(19 reviews)

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Berwyn

8% off
AU$1,562
for 7 nights, 1 apartment
AU$223 per night
includes taxes & fees
Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW
Upstairs queen bedroom 2
Downstairs living area
Kitchen (upstairs)
Fun Mirror Wall Upstairs
Exceptional
(97 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$12,340
for 7 nights, 1 apartment
AU$1,763 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Dining
Interior
Room
Living area
Exceptional
(24 reviews)

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Berwyn

8% off
AU$1,523
for 7 nights, 1 apartment
AU$218 per night
includes taxes & fees
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Queen Bedroom
Patio
Enjoy a meal in the dining room
Relax in the living room
Exceptional
(9 reviews)

Modern 2BR with Free Parking in Avondale

Chicago

7% off
AU$2,432
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Modern 2BR with Free Parking in Avondale
Living area
Exterior
Private kitchen
Property grounds
Very good
(30 reviews)

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago

7% off
AU$1,219
for 7 nights, 1 apartment
AU$174 per night
includes taxes & fees
Peaceful place Great location food markets transportation downtown lake Michigan
Living area
Dining
Private kitchen
Living area
Wonderful
(18 reviews)

Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI

Berwyn

8% off
AU$1,536
for 7 nights, 1 apartment
AU$219 per night
includes taxes & fees
Rustic APT /Near Hosp/ 25mins to ORD/MDW/DT/Free Parking & WIFI
Room
Living area
Private kitchen
Dining
Exceptional
(11 reviews)

Ridgeland Retreat/ Street level Apt easy access

Berwyn

8% off
AU$2,098
for 7 nights, 1 apartment
AU$300 per night
includes taxes & fees
Ridgeland Retreat/ Street level Apt easy access
Private kitchen
Interior
Living area
Interior
Wonderful
(84 reviews)

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago

5% off
AU$1,269
for 7 nights, 1 apartment
AU$181 per night
includes taxes & fees
Chic, Cozy home, by Blue Line Train Stop + Free parking
Private kitchen
Exterior
Dining
Room
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,664
for 7 nights, 1 apartment
AU$1,238 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Dining
Interior
Living area
Exterior
Exceptional
(13 reviews)

Spacious Duplex - 4BD/3BA - Sleeps 12!

Chicago

7% off
AU$4,723
for 7 nights, 1 apartment
AU$675 per night
includes taxes & fees
Spacious Duplex - 4BD/3BA - Sleeps 12!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Central Chicago getaway

Learn about the unique charm of Central Chicago with a stay in a holiday home rental. This city has something for everyone. Navy Pier and Michigan Avenue are a couple of places to search for that perfect souvenir. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Central Chicago

Do you want to discover things to do during your stay? Venture out of your holiday home and experience everything that makes Central Chicago a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (2.7 mi / 4.4 km)
  • Galloping Ghost (12.6 mi / 20.2 km)
  • The Dome at the Parkway Bank Sports Complex (14.4 mi / 23.2 km)
  • Oak Brook Golf Course (15.8 mi / 25.4 km)
  • The Glen Club (17.7 mi / 28.5 km)
  • Dave & Buster's (1.3 mi / 2.1 km)

Exploring the natural landscape of Central Chicago

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Central Chicago. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (0.3 mi / 0.4 km)
  • Grant Park (0.7 mi / 1.1 km)
  • Maggie Daley Park (0.5 mi / 0.7 km)
  • Ohio Street Beach (1.1 mi / 1.8 km)
  • Oak Street Beach (1.5 mi / 2.4 km)
  • Northerly Island (1.8 mi / 2.8 km)

Travelling to and around Central Chicago

If you prefer to travel by train, Millennium Station, Chicago Van Buren Street Station and Chicago Museum Campus-11th Street Station are the main stations in the city. You can get around Central Chicago by jumping on the metro at Madison-Wabash Station, Monroe Station (Red Line) or Monroe Station (Blue Line).

Frequently asked questions

How much does it cost to rent a holiday home in Central Chicago?
A number of things can determine the price of a holiday home in Central Chicago, including the type of property, season and length of stay. However, all of our holiday homes have one thing in common — exceptional value. Simply add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Central Chicago?
When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday home. Put in your Central Chicago travel dates to see all your options on Stayz. Did someone just say "hot tub"? Use the filters to pick the amenities and features you want in your holiday home.
What are the top attractions for families in Central Chicago?
There are tons of awesome things to do and see with the family in Central Chicago, such as:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
How old do you have to be to rent a holiday home in Central Chicago?
The age limit can differ across properties on Stayz, so check the rules of the holiday home in Central Chicago you want. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Central Chicago for?
The length of time you can book a holiday home in Central Chicago is up to the property. Simply enter your selected travel dates to view a list of options offering extended stays. With plenty of features like air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you're sure to find a terrific place to call your home away from home in Central Chicago.

More holiday ideas