Holiday rentals near Willis Tower
We found 3,611 holiday rentals — enter your dates for availability
Take a look at private holiday rentals close to Willis Tower that can be your home away from home. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for hanging out with the people that matter most, such as air conditioning and Wi-Fi. You'll be 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 - Willis Tower
Showing deals for:3 Oct - 10 Oct
Image gallery for Beautiful Downtown 3BR with Free Parking
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Beautiful Downtown 3BR with Free Parking
Chicago, IL
7% off
Price is NZ$9,259
NZ$9,259
NZ$1,323 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$14,171
NZ$14,171
NZ$2,024 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is NZ$7,737
NZ$7,737
NZ$1,105 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$9,083
NZ$9,083
NZ$1,298 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is NZ$2,999
NZ$2,999
NZ$428 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(39 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$7,083
NZ$7,083
NZ$1,012 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home
9.89.8 out of 10 rating
Exceptional
(27 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,183
NZ$4,183
NZ$598 per night
includes taxes & fees
Image gallery for #1810 - Kasa Magnificent Mile Chicago
9.29.2 out of 10 rating
Wonderful
(9 reviews)
#1810 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,055
NZ$4,055
NZ$579 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is NZ$6,700
NZ$6,700
NZ$957 per night
includes taxes & fees
Image gallery for Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
1010 out of 10 rating
Exceptional
(16 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Chicago, IL
7% off
Price is NZ$11,370
NZ$11,370
NZ$1,624 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, Illinois
7% off
Price is NZ$2,831
NZ$2,831
NZ$404 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
8% off
Price is NZ$11,317
NZ$11,317
NZ$1,617 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
(54 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,726
NZ$6,726
NZ$961 per night
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(5 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
8% off
Price is NZ$2,108
NZ$2,108
NZ$301 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$9,922
NZ$9,922
NZ$1,417 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is NZ$6,401
NZ$6,401
NZ$914 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,928
NZ$6,928
NZ$990 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is NZ$14,937
NZ$14,937
NZ$2,134 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$12,095
NZ$12,095
NZ$1,728 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is NZ$12,093
NZ$12,093
NZ$1,728 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,108
NZ$8,108
NZ$1,158 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
(38 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
7% off
Price is NZ$4,089
NZ$4,089
NZ$584 per night
includes taxes & fees
Image gallery for Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
8.48.4 out of 10 rating
Very good
(8 reviews)
Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
Chicago, IL
7% off
Price is NZ$2,038
NZ$2,038
NZ$291 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is NZ$3,236
NZ$3,236
NZ$462 per night
includes taxes & fees
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Find the best place to stay - Willis Tower
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
192 reviews(192 reviews)
31+Day Stay. 20 min Drive to Midway, South Loop, Beach, & Museums.
Sleeps 4 · 2 bedrooms · 1 bathroom
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
8.28.2 out of 10
Very goodvery good
109 reviews(109 reviews)
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sleeps 2 · 1 bedroom
8.28.2 out of 10
Very goodvery good
167 reviews(167 reviews)
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
317 reviews(317 reviews)
Fully-Equipped Suite | Gym Access
Sleeps 6 · 1 bedroom · 1 bathroom
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