Holiday rentals near Michigan Avenue
We found 2,826 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:15 Aug - 22 Aug
Image gallery for Chic 2BR 2BA Condo with Balcony - River North Chicago
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Chic 2BR 2BA Condo with Balcony - River North Chicago
Chicago, Illinois
8% off
Price is NZ$8,798
NZ$8,798
NZ$1,257 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
9.69.6 out of 10 rating
Exceptional
(37 reviews)
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
Chicago, Illinois
8% off
Price is NZ$7,056
NZ$7,056
NZ$1,008 per night
includes taxes & fees
Image gallery for 1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul
9.69.6 out of 10 rating
Exceptional
(11 reviews)
1600ft² Floor 19 PH w/ Best Views@WestLoop|TheSoul
Chicago, Illinois
8% off
Price is NZ$11,287
NZ$11,287
NZ$1,612 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$3,221
NZ$3,221
NZ$460 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$3,928
NZ$3,928
NZ$561 per night
includes taxes & fees
Image gallery for Gold Coast Retreat: Skyline Views, Walkable
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Gold Coast Retreat: Skyline Views, Walkable
Chicago, Illinois
8% off
Price is NZ$9,713
NZ$9,713
NZ$1,388 per night
includes taxes & fees
Image gallery for Why Guests Call This Chicago’s Best Spot|TheViolet
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Why Guests Call This Chicago’s Best Spot|TheViolet
Chicago, Illinois
7% off
Price is NZ$7,794
NZ$7,794
NZ$1,113 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$8,415
NZ$8,415
NZ$1,202 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$7,742
NZ$7,742
NZ$1,106 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$6,013
NZ$6,013
NZ$859 per night
includes taxes & fees
Image gallery for Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(226 reviews)
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,724
NZ$6,724
NZ$961 per night
includes taxes & fees
Image gallery for 4BR Lincoln Park Getaway: Steps to Red Line
9.89.8 out of 10 rating
Exceptional
(8 reviews)
4BR Lincoln Park Getaway: Steps to Red Line
Chicago, Illinois
7% off
Price is NZ$7,300
NZ$7,300
NZ$1,043 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
(46 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
7% off
Price is NZ$6,066
NZ$6,066
NZ$867 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(15 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$11,379
NZ$11,379
NZ$1,626 per night
includes taxes & fees
Image gallery for Why Settle for Ordinary?5 Stars Apartment|The Avant
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Why Settle for Ordinary?5 Stars Apartment|The Avant
Chicago, Illinois
8% off
Price is NZ$8,065
NZ$8,065
NZ$1,152 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
(86 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
8% off
Price is NZ$5,240
NZ$5,240
NZ$749 per night
includes taxes & fees
Image gallery for Best Group/Family Amenities in Downtown|The Cooke
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Best Group/Family Amenities in Downtown|The Cooke
Chicago, IL
8% off
Price is NZ$9,481
NZ$9,481
NZ$1,354 per night
includes taxes & fees
Image gallery for Kasa | Modern Studio + Steps to the South Loop | Chicago
9.49.4 out of 10 rating
Exceptional
(127 reviews)
Kasa | Modern Studio + Steps to the South Loop | Chicago
Chicago, Illinois
8% off
Price is NZ$3,668
NZ$3,668
NZ$524 per night
includes taxes & fees
Image gallery for Prime location Historic Chicago Townhouse
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Prime location Historic Chicago Townhouse
Chicago, Illinois
5% off
Price is NZ$17,762
NZ$17,762
NZ$2,537 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$10,433
NZ$10,433
NZ$1,490 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$10,433
NZ$10,433
NZ$1,490 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$6,211
NZ$6,211
NZ$887 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$3,928
NZ$3,928
NZ$561 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$5,337
NZ$5,337
NZ$762 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Michigan Avenue
Sonder The Opal
Sleeps 6 · 2 bedrooms
8.68.6 out of 10
Excellentexcellent
36 reviews(36 reviews)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
401 reviews(401 reviews)
Sonder Onterie
Sleeps 2 · 1 bedroom
8.48.4 out of 10
Very goodvery good
15 reviews(15 reviews)
Kasa River North Chicago
Sleeps 5 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
142 reviews(142 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
69 reviews(69 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)
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
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