Holiday rentals near Wintrust Arena
We found 2,678 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:18 Jul - 25 Jul
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$82,637
NZ$82,637
NZ$11,805 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,111
NZ$11,111
NZ$1,587 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$14,704
NZ$14,704
NZ$2,101 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$11,309
NZ$11,309
NZ$1,616 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$5,061
NZ$5,061
NZ$723 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
(38 reviews)
Stunning Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$7,598
NZ$7,598
NZ$1,085 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$13,774
NZ$13,774
NZ$1,968 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$7,527
NZ$7,527
NZ$1,075 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(12 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$15,942
NZ$15,942
NZ$2,277 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$4,629
NZ$4,629
NZ$661 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$11,309
NZ$11,309
NZ$1,616 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$4,614
NZ$4,614
NZ$659 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$9,637
NZ$9,637
NZ$1,377 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$4,260
NZ$4,260
NZ$609 per night
includes taxes & fees
Image gallery for Kasa | Classic 2 BD + Near Grant Park | Chicago
1010 out of 10 rating
Exceptional
(6 reviews)
Kasa | Classic 2 BD + Near Grant Park | Chicago
Chicago, Illinois
8% off
Price is NZ$9,282
NZ$9,282
NZ$1,326 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
Chicago, Illinois
8% off
Price is NZ$11,309
NZ$11,309
NZ$1,616 per night
includes taxes & fees
Image gallery for Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Stunning Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,632
NZ$7,632
NZ$1,090 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$4,260
NZ$4,260
NZ$609 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
7% off
Price is NZ$8,212
NZ$8,212
NZ$1,173 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$5,061
NZ$5,061
NZ$723 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
8.88.8 out of 10 rating
Excellent
(21 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$9,722
NZ$9,722
NZ$1,389 per night
includes taxes & fees
Image gallery for LakeHouse
1010 out of 10 rating
Exceptional
(16 reviews)
LakeHouse
Chicago, IL
22% off
Price is NZ$3,668
NZ$3,668
NZ$524 per night
includes taxes & fees
Image gallery for Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
1010 out of 10 rating
Exceptional
(8 reviews)
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Chicago, IL
12% off
Price is NZ$7,424
NZ$7,424
NZ$1,061 per night
includes taxes & fees
Image gallery for Chic 4-Bedroom Haven: Designer's Dream Home
1010 out of 10 rating
Exceptional
(5 reviews)
Chic 4-Bedroom Haven: Designer's Dream Home
Chicago, Illinois
12% off
Price is NZ$11,608
NZ$11,608
NZ$1,658 per night
includes taxes & fees
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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
473 reviews(473 reviews)
Stunning 3 BR in prime Chicago location
Sleeps 5 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
93 reviews(93 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
65 reviews(65 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
728 reviews(728 reviews)
Sunny Jumbo Studio in the Heart of Oak Park
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Stunning Condo #2 - Downtown River North!
Sleeps 14 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
16 reviews(16 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