Holiday rentals near Midway Plaisance
We found 2,300 holiday rentals — enter your dates for availability
Take a look at holiday rentals near Midway Plaisance that can be your home away from home. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Midway Plaisance
Showing deals for:7 Nov - 14 Nov
Image gallery for Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
1010 out of 10 rating
Exceptional
(7 reviews)
Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
Chicago, IL
7% off
Price is AU$7,525
AU$7,525
AU$1,075 per night
includes taxes & fees
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(6 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
7% off
Price is AU$6,510
AU$6,510
AU$930 per night
includes taxes & fees
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.08.0 out of 10 rating
Very good
(14 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
10% off
Price is AU$5,075
AU$5,075
AU$725 per night
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is AU$5,028
AU$5,028
AU$718 per night
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
8% off
Price is AU$38,973
AU$38,973
AU$5,568 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
7% off
Price is AU$9,494
AU$9,494
AU$1,356 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.89.8 out of 10 rating
Exceptional
(11 reviews)
3BR Luxury Modern Apartment
Chicago, IL
7% off
Price is AU$6,224
AU$6,224
AU$889 per night
includes taxes & fees
Image gallery for #1902 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1902 - Kasa Magnificent Mile Chicago
Chicago, IL
8% off
Price is AU$4,640
AU$4,640
AU$663 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, IL
8% off
Price is AU$6,124
AU$6,124
AU$875 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
7% off
Price is AU$6,594
AU$6,594
AU$942 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is AU$5,641
AU$5,641
AU$806 per night
includes taxes & fees
Image gallery for The Loop 2BR: Historic, Modern Luxury, Amenities
1010 out of 10 rating
Exceptional
(5 reviews)
The Loop 2BR: Historic, Modern Luxury, Amenities
Chicago, IL
7% off
Price is AU$5,551
AU$5,551
AU$793 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 2
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 2
Chicago, IL
15% off
Price is AU$6,001
AU$6,001
AU$857 per night
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is AU$8,048
AU$8,048
AU$1,150 per night
includes taxes & fees
Image gallery for Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
Chicago, IL
7% off
Price is AU$7,374
AU$7,374
AU$1,053 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
(56 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
7% off
Price is AU$6,252
AU$6,252
AU$893 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, IL
7% off
Price is AU$8,041
AU$8,041
AU$1,149 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(15 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is AU$10,489
AU$10,489
AU$1,498 per night
includes taxes & fees
Image gallery for Penthouse Corner 3BR in Streeterville | Roof Deck
9.49.4 out of 10 rating
Exceptional
(23 reviews)
Penthouse Corner 3BR in Streeterville | Roof Deck
Chicago, IL
7% off
Price is AU$6,009
AU$6,009
AU$858 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, IL
7% off
Price is AU$6,016
AU$6,016
AU$859 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(28 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is AU$9,121
AU$9,121
AU$1,303 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
7% off
Price is AU$10,102
AU$10,102
AU$1,443 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, IL
8% off
Price is AU$2,469
AU$2,469
AU$353 per night
includes taxes & fees
Image gallery for Gorgeous N. Kenwood/Hyde Park
8.08.0 out of 10 rating
Very good
(7 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is AU$3,303
AU$3,303
AU$472 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Midway Plaisance
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
459 reviews(459 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
335 reviews(335 reviews)
Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower
Sleeps 2 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
82 reviews(82 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
182 reviews(182 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
860 reviews(860 reviews)
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
338 reviews(338 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