Holiday rentals near Maxwell Street Market
We found 3,372 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals near Maxwell Street Market that can be your home away from home. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include a pool and a washer and dryer. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Maxwell Street Market
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$9,671
NZ$9,671
NZ$1,382 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$3,893
NZ$3,893
NZ$556 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$8,141
NZ$8,141
NZ$1,163 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$10,477
NZ$10,477
NZ$1,497 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$3,193
NZ$3,193
NZ$456 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$9,089
NZ$9,089
NZ$1,298 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$7,373
NZ$7,373
NZ$1,053 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$6,033
NZ$6,033
NZ$862 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$6,748
NZ$6,748
NZ$964 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,736
NZ$8,736
NZ$1,248 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(14 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
7% off
Price is NZ$12,571
NZ$12,571
NZ$1,796 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$5,229
NZ$5,229
NZ$747 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$9,115
NZ$9,115
NZ$1,302 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$17,503
NZ$17,503
NZ$2,500 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$3,726
NZ$3,726
NZ$532 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$4,435
NZ$4,435
NZ$634 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
1010 out of 10 rating
Exceptional
(12 reviews)
Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
Chicago, Illinois
8% off
Price is NZ$4,042
NZ$4,042
NZ$577 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$4,974
NZ$4,974
NZ$711 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$10,477
NZ$10,477
NZ$1,497 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$3,893
NZ$3,893
NZ$556 per night
includes taxes & fees
Image gallery for Stylish Two Bedroom - A block from Wrigley Field
1010 out of 10 rating
Exceptional
(22 reviews)
Stylish Two Bedroom - A block from Wrigley Field
Chicago, IL
8% off
Price is NZ$6,453
NZ$6,453
NZ$922 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,159
NZ$6,159
NZ$880 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$7,260
NZ$7,260
NZ$1,037 per night
includes taxes & fees
Image gallery for Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deck
9.49.4 out of 10 rating
Exceptional
(41 reviews)
Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deck
Chicago, IL
7% off
Price is NZ$6,044
NZ$6,044
NZ$863 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Maxwell Street Market
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
68 reviews(68 reviews)
Sonder Onterie
Sleeps 2 · 1 bedroom
8.28.2 out of 10
Very goodvery good
14 reviews(14 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
311 reviews(311 reviews)
Sonder Market Hall
Sleeps 2 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
279 reviews(279 reviews)
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
399 reviews(399 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