Holiday rentals near Michigan Avenue
We found 3,049 holiday rentals — enter your dates for availability
Take a look at private holiday rentals near Michigan Avenue that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Michigan Avenue
Showing deals for:3 Oct - 10 Oct
Image gallery for Beautiful Downtown 3BR with Free Parking
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Beautiful Downtown 3BR with Free Parking
Chicago, IL
7% off
Price is NZ$9,214
NZ$9,214
NZ$1,316 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$14,132
NZ$14,132
NZ$2,019 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$9,040
NZ$9,040
NZ$1,291 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(39 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$7,048
NZ$7,048
NZ$1,007 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$6,907
NZ$6,907
NZ$987 per night
includes taxes & fees
Image gallery for Kasa | Relaxing Studio + Pet Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Kasa | Relaxing Studio + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$4,415
NZ$4,415
NZ$631 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is NZ$2,958
NZ$2,958
NZ$423 per night
includes taxes & fees
Image gallery for #1810 - Kasa Magnificent Mile Chicago
9.29.2 out of 10 rating
Wonderful
(9 reviews)
#1810 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,036
NZ$4,036
NZ$577 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$11,346
NZ$11,346
NZ$1,621 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
8% off
Price is NZ$14,870
NZ$14,870
NZ$2,124 per night
includes taxes & fees
Image gallery for Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
1010 out of 10 rating
Exceptional
(16 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Chicago, IL
7% off
Price is NZ$11,449
NZ$11,449
NZ$1,636 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
(54 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,649
NZ$6,649
NZ$950 per night
includes taxes & fees
Image gallery for Kasa | Modern 2 BD + Near Local Eateries | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Modern 2 BD + Near Local Eateries | Chicago
Chicago, Illinois
8% off
Price is NZ$6,807
NZ$6,807
NZ$972 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$12,071
NZ$12,071
NZ$1,724 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is NZ$6,370
NZ$6,370
NZ$910 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
(26 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,840
NZ$6,840
NZ$977 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
11% off
Price is NZ$12,062
NZ$12,062
NZ$1,723 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$7,964
NZ$7,964
NZ$1,138 per night
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, Illinois
7% off
Price is NZ$2,808
NZ$2,808
NZ$401 per night
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(38 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
7% off
Price is NZ$4,069
NZ$4,069
NZ$581 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago, IL
8% off
Price is NZ$9,618
NZ$9,618
NZ$1,374 per night
includes taxes & fees
Image gallery for Lakefront property , minutes from McCormick Place and Downtown Chicago.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago, IL
11% off
Price is NZ$6,919
NZ$6,919
NZ$988 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is NZ$3,221
NZ$3,221
NZ$460 per night
includes taxes & fees
Image gallery for The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway!
Chicago, IL
16% off
Price is NZ$5,117
NZ$5,117
NZ$731 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Michigan Avenue
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
435 reviews(435 reviews)
Sonder by Marriott Bonvoy The Opal Apartments River North
Sleeps 6 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
40 reviews(40 reviews)
5 BR / 3.5 BA Newly Built Home in Logan Square!
Sleeps 10 · 5 bedrooms · 3+ bathrooms
8.48.4 out of 10
Very goodvery good
15 reviews(15 reviews)
Kasa River North Chicago
Sleeps 5 · 2 bedrooms
9.69.6 out of 10
Exceptionalexceptional
152 reviews(152 reviews)
Spacious Wicker Park Hideaway with Parking!
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
12 reviews(12 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
77 reviews(77 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