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 AU$8,375
AU$8,375
AU$1,196 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
8% off
Price is AU$12,728
AU$12,728
AU$1,818 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
1010 out of 10 rating
Exceptional
(31 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is AU$6,980
AU$6,980
AU$997 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 AU$8,216
AU$8,216
AU$1,174 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 AU$2,756
AU$2,756
AU$394 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 AU$6,542
AU$6,542
AU$935 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 AU$3,849
AU$3,849
AU$550 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 AU$3,726
AU$3,726
AU$532 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 AU$6,174
AU$6,174
AU$882 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 AU$10,567
AU$10,567
AU$1,510 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 AU$2,603
AU$2,603
AU$372 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 AU$10,526
AU$10,526
AU$1,504 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 AU$6,200
AU$6,200
AU$886 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 AU$1,937
AU$1,937
AU$277 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 AU$9,209
AU$9,209
AU$1,316 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 AU$5,894
AU$5,894
AU$842 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 AU$6,391
AU$6,391
AU$913 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 AU$13,449
AU$13,449
AU$1,921 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 AU$11,250
AU$11,250
AU$1,607 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 AU$11,247
AU$11,247
AU$1,607 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 AU$7,328
AU$7,328
AU$1,047 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
8% off
Price is AU$3,757
AU$3,757
AU$537 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 AU$1,909
AU$1,909
AU$273 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
9% off
Price is AU$2,978
AU$2,978
AU$425 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Willis Tower
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Find the best place to stay - Willis Tower
Showing deals for: 2 Oct - 5 Oct
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
192 reviews(192 reviews)
The current price is AU$1,573
AU$1,573
for 3 nights, 1 room
AU$524 per night
includes taxes & fees
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)
The current price is AU$1,579
AU$1,579
for 3 nights, 1 room
AU$526 per night
includes taxes & fees
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)
The current price is AU$1,399
AU$1,399
for 3 nights, 1 room
AU$466 per night
includes taxes & fees
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
317 reviews(317 reviews)
The current price is AU$1,428
AU$1,428
for 3 nights, 1 room
AU$476 per night
includes taxes & fees
Sonder by Marriott Bonvoy Greektown Apartments
Sleeps 4 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
55 reviews(55 reviews)
The current price is AU$1,711
AU$1,711
for 3 nights, 1 room
AU$570 per night
includes taxes & fees
Sleek North Side Studio Apartment
Sleeps 2 · 1 bedroom · 1 bathroom
2.02.0 out of 10
1 review(1 review)
The current price is AU$1,795
AU$1,795
for 3 nights, 1 home
AU$598 per night
includes taxes & fees
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