Holiday rentals near Wintrust Arena
We found 2,902 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals near Wintrust Arena that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a fireplace. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Wintrust Arena
Showing deals for:19 Sept - 26 Sept
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(20 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
7% off
Price is NZ$57,534
NZ$57,534
NZ$8,219 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$10,766
NZ$10,766
NZ$1,538 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
7% off
Price is NZ$13,059
NZ$13,059
NZ$1,866 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Chicago, IL
7% off
Price is NZ$11,808
NZ$11,808
NZ$1,687 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$2,985
NZ$2,985
NZ$426 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,678
NZ$3,678
NZ$525 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$8,238
NZ$8,238
NZ$1,177 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$10,219
NZ$10,219
NZ$1,460 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
8% off
Price is NZ$11,415
NZ$11,415
NZ$1,631 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$7,620
NZ$7,620
NZ$1,089 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$10,138
NZ$10,138
NZ$1,448 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is NZ$8,996
NZ$8,996
NZ$1,285 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,107
NZ$6,107
NZ$872 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,920
NZ$6,920
NZ$989 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(31 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is NZ$7,656
NZ$7,656
NZ$1,094 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
(51 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$7,340
NZ$7,340
NZ$1,049 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(6 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
7% off
Price is NZ$6,133
NZ$6,133
NZ$876 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(18 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
8% off
Price is NZ$11,600
NZ$11,600
NZ$1,657 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$3,119
NZ$3,119
NZ$446 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 2
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Beautiful Unit CHI in Prime River North - 2
Chicago, Illinois
15% off
Price is NZ$6,666
NZ$6,666
NZ$952 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$10,219
NZ$10,219
NZ$1,460 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,678
NZ$3,678
NZ$525 per night
includes taxes & fees
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(5 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
8% off
Price is NZ$6,704
NZ$6,704
NZ$958 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,678
NZ$3,678
NZ$525 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Wintrust Arena
Showing deals for: 14 Sept - 17 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sleeps 4 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
535 reviews(535 reviews)
The current price is NZ$1,531
NZ$1,531
for 3 nights, 1 room
NZ$510 per night
includes taxes & fees
South Shore Retreat 5 bedrooms/entertainment
Sleeps 12 · 5 bedrooms · 2+ bathrooms
8.08.0 out of 10
Very goodvery good
3 reviews(3 reviews)
The current price is NZ$1,866
NZ$1,866
for 3 nights, 1 home
NZ$622 per night
includes taxes & fees
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Sleeps 10 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is NZ$3,831
NZ$3,831
for 3 nights, 1 home
NZ$1,277 per night
includes taxes & fees
Don't miss out on this one! No cleaning fee. Ideal for McCormick Center visits.
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
The current price is NZ$839
NZ$839
for 3 nights, 1 apartment
NZ$280 per night
includes taxes & fees
Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
71 reviews(71 reviews)
The current price is NZ$1,199
NZ$1,199
for 3 nights, 1 room
NZ$400 per night
includes taxes & fees
Gorgeous N. Kenwood/Hyde Park
Sleeps 11 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is NZ$2,329
NZ$2,329
for 3 nights, 1 apartment
NZ$776 per night
includes taxes & fees
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