Holiday rentals near Wintrust Sports Complex

We found 3,632 holiday rentals — enter your dates for availability

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September 2025

October 2025

Holiday rentals with weekly discounts - Wintrust Sports Complex

Showing deals for:26 Dec - 2 Jan

Loft Living Space with Deep, Comfortable Sofa, Smart Flat Screen TV & Fireplace

Exceptional

(52 reviews)

Luxury House in the heart of Old Town with Parking

Chicago, IL

11% off

for 7 nights, 1 home

AU$3,149 per night

includes taxes & fees

The apartment is flooded with beautiful light from multiple sides

Exceptional

(56 reviews)

Chic Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,139 per night

includes taxes & fees

Beautiful view from our oversize living room window

Wonderful

(44 reviews)

Modern 3BR Penthouse in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,529 per night

includes taxes & fees

The open living room and dining area is flooded with light during the day

Exceptional

(5 reviews)

Splendid Corner 3BR in the Loop | City Views

Chicago, IL

7% off

for 7 nights, 1 home

AU$1,405 per night

includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(60 reviews)

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,240 per night

includes taxes & fees

Living Room / Dining Room with Fully stocked kitchen

Living Room has pullout couch (denim colored sofa)

Exceptional

(7 reviews)

Historic and Unique Brownstone in Gold Coast - 3

Chicago, IL

13% off

for 7 nights, 1 apartment

AU$304 per night

includes taxes & fees

Exceptional

(61 reviews)

Stylish Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,047 per night

includes taxes & fees

Exceptional

(18 reviews)

Splendid Corner 3BR in the Loop | City Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,405 per night

includes taxes & fees

Exceptional

(13 reviews)

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

Oak Park, IL

7% off

for 7 nights, 1 home

AU$368 per night

includes taxes & fees

Exceptional

(45 reviews)

Stunning Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,100 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(31 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$872 per night

includes taxes & fees

Exceptional

(38 reviews)

Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$809 per night

includes taxes & fees

Exceptional

(44 reviews)

Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$797 per night

includes taxes & fees

Exceptional

(31 reviews)

Chic Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$813 per night

includes taxes & fees

Exceptional

(31 reviews)

Stunning 3BR Penthouse in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,607 per night

includes taxes & fees

Corner unit with awesome light and views

Wonderful

(15 reviews)

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$2,254 per night

includes taxes & fees

Wonderful

(37 reviews)

Spectacular Corner 2BR Penthouse in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

AU$1,272 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Top rated rentals - Wintrust Sports Complex

Premier Host

Good location plenty of room

Host was terrific. Easy and direct communication. House was as presented. Well equipped, tidy, spacious and comfortable. Location: easy access to shops and city on train. Little things let it down - missing or broken lights, squeaky doors. A bit noisy with the L on back fence, but we did know that.

Sarah Jane V.

Stayed Oct 2024

Premier Host

Fabulous

The property is a fully equipped home, has everything you need and makes life simple while you are there. The owner is also right next door and very responsive, friendly and helpful. Taylor street is a very short walk away, the pink line is a short walk away, great location, very quiet.

Robin N.

Stayed July 2024

Premier Host

Perfect place for our visit

We loved this cosey home and really appreciated all the little things the owners had thought about to make our stay enjoyable. Definitely recommend!

Daniel S.

Stayed Mar 2023

Peace of mind
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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
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