Holiday rentals near Wintrust Arena
We found 2,832 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:1 Aug - 8 Aug
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
8% off
Price is NZ$87,455
NZ$87,455
NZ$12,494 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$105,199
NZ$105,199
NZ$15,028 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
8% off
Price is NZ$14,928
NZ$14,928
NZ$2,133 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
12% off
Price is NZ$14,882
NZ$14,882
NZ$2,126 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$10,842
NZ$10,842
NZ$1,549 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$5,491
NZ$5,491
NZ$784 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,654
NZ$4,654
NZ$665 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
7% off
Price is NZ$13,484
NZ$13,484
NZ$1,926 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
(32 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$9,050
NZ$9,050
NZ$1,293 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(13 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$16,548
NZ$16,548
NZ$2,364 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
9.09.0 out of 10 rating
Wonderful
(21 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$11,860
NZ$11,860
NZ$1,694 per night
includes taxes & fees
Image gallery for Chic & Historic Apartment Steps from Mag Mile
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Chic & Historic Apartment Steps from Mag Mile
Chicago, IL
8% off
Price is NZ$6,211
NZ$6,211
NZ$887 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(5 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
7% off
Price is NZ$9,394
NZ$9,394
NZ$1,342 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,968
NZ$4,968
NZ$710 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$15,360
NZ$15,360
NZ$2,194 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$5,491
NZ$5,491
NZ$784 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,654
NZ$4,654
NZ$665 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$4,654
NZ$4,654
NZ$665 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$5,491
NZ$5,491
NZ$784 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
(25 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
8% off
Price is NZ$9,693
NZ$9,693
NZ$1,385 per night
includes taxes & fees
Image gallery for Large historic home minutes from downtown Chicago and the lakefront.
1010 out of 10 rating
Exceptional
(8 reviews)
Large historic home minutes from downtown Chicago and the lakefront.
Chicago, IL
8% off
Price is NZ$9,665
NZ$9,665
NZ$1,381 per night
includes taxes & fees
Image gallery for Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
Chicago, IL
12% off
Price is NZ$11,647
NZ$11,647
NZ$1,664 per night
includes taxes & fees
Image gallery for Gorgeous NEW 5 BDR/ 4BA in Logan Square w/Parking!
9.29.2 out of 10 rating
Wonderful
(41 reviews)
Gorgeous NEW 5 BDR/ 4BA in Logan Square w/Parking!
Chicago, IL
8% off
Price is NZ$15,714
NZ$15,714
NZ$2,245 per night
includes taxes & fees
Image gallery for Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
Chicago, IL
8% off
Price is NZ$7,383
NZ$7,383
NZ$1,055 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Wintrust Arena
Sonder South Wabash
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
486 reviews(486 reviews)
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
67 reviews(67 reviews)
Stunning 3 BR in prime Chicago location
Sleeps 5 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
River North Gem! Near Magnificent Mile and Chicago Riverwalk! Pets Allowed.
Sleeps 2 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
739 reviews(739 reviews)
Kasa South Loop Chicago
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
280 reviews(280 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