Holiday rentals with weekly discounts – Central Chicago
Showing deals for:12 Feb - 19 Feb
Image gallery for Chicago Gold Coast Mansion 6 Bed Luxury Retreat
1010 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Chicago Gold Coast Mansion 6 Bed Luxury Retreat
Chicago
8% off
Price is AU$27,518
AU$27,518
for 7 nights, 1 home
AU$3,931 per night
includes taxes & fees
Image gallery for Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
9.89.8 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
8% off
Price is AU$14,199
AU$14,199
for 7 nights, 1 apartment
AU$2,028 per night
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10, Exceptional, (107 reviews)
Exceptional
(107 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago
7% off
Price is AU$4,679
AU$4,679
for 7 nights, 1 apartment
AU$668 per night
includes taxes & fees
Image gallery for Stunning Lincoln Park Single-Family House with Fantastic Game Room
1010 out of 10, Exceptional, (93 reviews)
Exceptional
(93 reviews)
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Chicago
11% off
Price is AU$10,170
AU$10,170
for 7 nights, 1 home
AU$1,453 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.89.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago
8% off
Price is AU$6,124
AU$6,124
for 7 nights, 1 home
AU$875 per night
includes taxes & fees
Image gallery for The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Chicago
7% off
Price is AU$7,724
AU$7,724
for 7 nights, 1 apartment
AU$1,103 per night
includes taxes & fees
Image gallery for Beautiful Berwyn Bungalow Close to Downtown Chicago
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Beautiful Berwyn Bungalow Close to Downtown Chicago
Berwyn
8% off
Price is AU$3,388
AU$3,388
for 7 nights, 1 home
AU$484 per night
includes taxes & fees
Image gallery for Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
9.49.4 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT
Berwyn
8% off
Price is AU$1,650
AU$1,650
for 7 nights, 1 apartment
AU$236 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house with cinema room massage chair in peaceful Evanston
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Charming 3-bedroom house with cinema room massage chair in peaceful Evanston
Evanston
8% off
Price is AU$3,793
AU$3,793
for 7 nights, 1 home
AU$542 per night
includes taxes & fees
Image gallery for Steps from the “L” train to Wrigley & Downtown
1010 out of 10, Exceptional, (69 reviews)
Exceptional
(69 reviews)
Steps from the “L” train to Wrigley & Downtown
Chicago
8% off
Price is AU$4,861
AU$4,861
for 7 nights, 1 apartment
AU$694 per night
includes taxes & fees
Image gallery for The En Bronze ~ 7mins To Dining & Downtown Chicago
9.29.2 out of 10, Wonderful, (9 reviews)
Wonderful
(9 reviews)
The En Bronze ~ 7mins To Dining & Downtown Chicago
Chicago
7% off
Price is AU$5,840
AU$5,840
for 7 nights, 1 apartment
AU$834 per night
includes taxes & fees
Image gallery for Premier 4BR Art Deco suite with garage.
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Premier 4BR Art Deco suite with garage.
Chicago
6% off
Price is AU$6,826
AU$6,826
for 7 nights, 1 apartment
AU$975 per night
includes taxes & fees
Image gallery for A home away from home! <No events allowed>
9.69.6 out of 10, Exceptional, (160 reviews)
Exceptional
(160 reviews)
A home away from home! <No events allowed>
Chicago
7% off
Price is AU$2,545
AU$2,545
for 7 nights, 1 home
AU$364 per night
includes taxes & fees
Image gallery for Wrigley Field/Lakeview -Entire Home- Large Groups!
9.89.8 out of 10, Exceptional, (116 reviews)
Exceptional
(116 reviews)
Wrigley Field/Lakeview -Entire Home- Large Groups!
Chicago
11% off
Price is AU$7,665
AU$7,665
for 7 nights, 1 home
AU$1,095 per night
includes taxes & fees
Image gallery for 2,400 SF 4BR + 2 Parking | Steps to Wrigley
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
2,400 SF 4BR + 2 Parking | Steps to Wrigley
Chicago
8% off
Price is AU$6,471
AU$6,471
for 7 nights, 1 apartment
AU$924 per night
includes taxes & fees
Image gallery for Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
9.89.8 out of 10, Exceptional, (121 reviews)
Exceptional
(121 reviews)
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Chicago
23% off
Price is AU$2,199
AU$2,199
for 7 nights, 1 apartment
AU$314 per night
includes taxes & fees
Image gallery for Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
1010 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
8% off
Price is AU$8,165
AU$8,165
for 7 nights, 1 home
AU$1,166 per night
includes taxes & fees
Image gallery for Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago
Chicago
10% off
Price is AU$2,996
AU$2,996
for 7 nights, 1 apartment
AU$428 per night
includes taxes & fees
Image gallery for Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
9.69.6 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Peaceful and Lovely 3-bedroom house near MDW. Furry friends welcomed
Chicago
8% off
Price is AU$2,131
AU$2,131
for 7 nights, 1 home
AU$304 per night
includes taxes & fees
Image gallery for 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
9.49.4 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Chicago
7% off
Price is AU$3,343
AU$3,343
for 7 nights, 1 apartment
AU$478 per night
includes taxes & fees
Image gallery for Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
9.09.0 out of 10, Wonderful, (45 reviews)
Wonderful
(45 reviews)
Classy Apt/Comfy Beds/25mins to ORD>MDW>DT>HOSP
Berwyn
8% off
Price is AU$1,918
AU$1,918
for 7 nights, 1 apartment
AU$274 per night
includes taxes & fees
Image gallery for Ravenswood Loft
8.88.8 out of 10, Excellent, (15 reviews)
Excellent
(15 reviews)
Ravenswood Loft
Chicago
16% off
Price is AU$1,927
AU$1,927
for 7 nights, 1 apartment
AU$275 per night
includes taxes & fees
Image gallery for Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
9.89.8 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Historic feel, Modern comfort Walk to parks and food in beautiful Chicago
Chicago
7% off
Price is AU$1,965
AU$1,965
for 7 nights, 1 apartment
AU$281 per night
includes taxes & fees
Image gallery for High-end 2Bdrm Garden Apt. Where Comfort Meets Style
9.29.2 out of 10, Wonderful, (17 reviews)
Wonderful
(17 reviews)
High-end 2Bdrm Garden Apt. Where Comfort Meets Style
Chicago
7% off
Price is AU$2,049
AU$2,049
for 7 nights, 1 apartment
AU$293 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Central Chicago
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Find the best place to stay - Central Chicago
Sentral Michigan Avenue
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
1,405 reviews(1,405 reviews)
Hyde Park Duplex
Sleeps 10 · 6 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
Lakefront designer condo with private parking, 7 min to Obama Center
Sleeps 10 · 4 bedrooms · 2 bathrooms
Extra Large Authentic Chicago Graystone walk to Wrigley, Lakefront & Restaurants
Sleeps 20 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
Kasa Magnificent Mile Chicago
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
998 reviews(998 reviews)
Luxury 1BR Chicago Retreat downtown Free Parking, Gym, Theater & Patio
Sleeps 2 · 1 bedroom · 1+ bathroom
4.04.0 out of 10
1 review(1 review)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
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.