Photo by Meredith Breckner
Holiday rentals near Daley Plaza
We found 3,072 holiday rentals — enter your dates for availability
Choose the right holiday home that's close to Daley Plaza. Holiday rentals provide the best amenities for your family, friends or furry companion, such as a fireplace and garden. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Daley Plaza
Showing deals for:14 Nov - 21 Nov
Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.29.2 out of 10 rating
Wonderful
(50 reviews)
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Chicago, IL
13% off
Price is NZ$3,126
NZ$3,126
NZ$447 per night
includes taxes & fees
Image gallery for Chic & Historic Apartment Steps from Mag Mile
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Chic & Historic Apartment Steps from Mag Mile
Chicago, IL
6% off
Price is NZ$2,068
NZ$2,068
NZ$295 per night
includes taxes & fees
Image gallery for Downtown Charm: 2BR, Comfort, Great Amenities
1010 out of 10 rating
Exceptional
(6 reviews)
Downtown Charm: 2BR, Comfort, Great Amenities
Chicago, IL
7% off
Price is NZ$5,543
NZ$5,543
NZ$792 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 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is NZ$5,459
NZ$5,459
NZ$780 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.29.2 out of 10 rating
Wonderful
(13 reviews)
3BR Luxury Modern Apartment
Chicago, IL
7% off
Price is NZ$5,365
NZ$5,365
NZ$766 per night
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
22% off
Price is NZ$35,602
NZ$35,602
NZ$5,086 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is NZ$5,312
NZ$5,312
NZ$759 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
7% off
Price is NZ$8,591
NZ$8,591
NZ$1,227 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
7% off
Price is NZ$6,065
NZ$6,065
NZ$866 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
7% off
Price is NZ$5,884
NZ$5,884
NZ$841 per night
includes taxes & fees
Image gallery for Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
Chicago, IL
7% off
Price is NZ$10,959
NZ$10,959
NZ$1,566 per night
includes taxes & fees
Image gallery for Brownstone in Gold Coast - Downtown
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Brownstone in Gold Coast - Downtown
Chicago, IL
13% off
Price is NZ$1,758
NZ$1,758
NZ$251 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
7% off
Price is NZ$4,346
NZ$4,346
NZ$621 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(30 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,495
NZ$4,495
NZ$642 per night
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, IL
6% off
Price is NZ$1,805
NZ$1,805
NZ$258 per night
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
14% off
Price is NZ$3,737
NZ$3,737
NZ$534 per night
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
7% off
Price is NZ$5,694
NZ$5,694
NZ$813 per night
includes taxes & fees
Image gallery for Studio flat in the heart of Chicago's Gold Coast
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Studio flat in the heart of Chicago's Gold Coast
Chicago, IL
5% off
Price is NZ$1,386
NZ$1,386
NZ$198 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(20 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$7,356
NZ$7,356
NZ$1,051 per night
includes taxes & fees
Image gallery for Trendy|Comfortable|1BR|Lincoln Square
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Trendy|Comfortable|1BR|Lincoln Square
Chicago, IL
7% off
Price is NZ$4,001
NZ$4,001
NZ$572 per night
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
7% off
Price is NZ$2,224
NZ$2,224
NZ$318 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
7% off
Price is NZ$5,206
NZ$5,206
NZ$744 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
13% off
Price is NZ$2,023
NZ$2,023
NZ$289 per night
includes taxes & fees
Image gallery for Stylish Corner 2BR in the Loop | City & Lake Views
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Stylish Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is NZ$5,427
NZ$5,427
NZ$775 per night
includes taxes & fees
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Find the best place to stay - Daley Plaza
Cozy, Fully Set-Up 1BR Space
Sleeps 2 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
14 reviews(14 reviews)
Dazzling Downtown Stay Near Riverwalk & Museums | 4 Amazing Rooms
Sleeps 16 · 4 bedrooms · 4 bathrooms
GARAGE PARKING! Stay in, Walk to Great Local Spots, Grab the CTA, or Hop on I-290 - the Perfect Location for All Your Adventures by AllSet Turnover
Sleeps 8 · 4 bedrooms · 3+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
12 reviews(12 reviews)
Group Vacation! 4 Comfortable Units, Indoor Pool, Rooftop Deck
Sleeps 16 · 4 bedrooms · 4 bathrooms
8.88.8 out of 10
Excellentexcellent
5 reviews(5 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
NEW LUXURY CONDO WITH PATIO DECK
Sleeps 5 · 1 bedroom · 1+ bathroom
1010 out of 10
Exceptionalexceptional
176 reviews(176 reviews)
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