Holiday rentals near Maxwell Street Market
We found 3,622 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:10 Oct - 17 Oct
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
8% off
Price is AU$13,600
AU$13,600
AU$1,943 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 AU$10,915
AU$10,915
AU$1,559 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 AU$6,088
AU$6,088
AU$870 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 AU$14,569
AU$14,569
AU$2,081 per night
includes taxes & fees
Image gallery for #1402 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(25 reviews)
#1402 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$9,519
AU$9,519
AU$1,360 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 AU$9,490
AU$9,490
AU$1,356 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
8% off
Price is AU$14,337
AU$14,337
AU$2,048 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 AU$6,516
AU$6,516
AU$931 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
1010 out of 10 rating
Exceptional
(31 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is AU$7,594
AU$7,594
AU$1,085 per night
includes taxes & fees
Image gallery for Luxury SOHO Styled Two-Level Townhouse - Old Town
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury SOHO Styled Two-Level Townhouse - Old Town
Chicago, Illinois
8% off
Price is AU$12,665
AU$12,665
AU$1,809 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 AU$3,608
AU$3,608
AU$515 per night
includes taxes & fees
Image gallery for Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
1010 out of 10 rating
Exceptional
(18 reviews)
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Willowbrook, IL
8% off
Price is AU$2,999
AU$2,999
AU$428 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 AU$3,441
AU$3,441
AU$492 per night
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
8% off
Price is AU$14,891
AU$14,891
AU$2,127 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 AU$4,746
AU$4,746
AU$678 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(20 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
8% off
Price is AU$14,112
AU$14,112
AU$2,016 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 AU$7,078
AU$7,078
AU$1,011 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
8% off
Price is AU$12,902
AU$12,902
AU$1,843 per night
includes taxes & fees
Image gallery for Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Modern 3-Bed Stay w/ Patio & Firepit, 15 Minutes to Downtown
Chicago, IL
11% off
Price is AU$5,800
AU$5,800
AU$829 per night
includes taxes & fees
Image gallery for Spacious 5-Bedroom Retreat in Forest Park
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 5-Bedroom Retreat in Forest Park
Forest Park, IL
34% off
Price is AU$7,064
AU$7,064
AU$1,009 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(17 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$7,078
AU$7,078
AU$1,011 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 AU$7,078
AU$7,078
AU$1,011 per night
includes taxes & fees
Image gallery for Stunning & Spacious 7BD Home with garage!
8.48.4 out of 10 rating
Very good
(5 reviews)
Stunning & Spacious 7BD Home with garage!
Chicago, IL
7% off
Price is AU$12,558
AU$12,558
AU$1,794 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 AU$6,088
AU$6,088
AU$870 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Maxwell Street Market
Showing deals for: 5 Oct - 8 Oct
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
323 reviews(323 reviews)
The current price is AU$1,372
AU$1,372
for 3 nights, 1 room
AU$457 per night
includes taxes & fees
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
437 reviews(437 reviews)
The current price is AU$1,238
AU$1,238
for 3 nights, 1 room
AU$413 per night
includes taxes & fees
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)
The current price is AU$1,782
AU$1,782
for 3 nights, 1 room
AU$594 per night
includes taxes & fees
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
808 reviews(808 reviews)
The current price is AU$1,499
AU$1,499
for 3 nights, 1 room
AU$500 per night
includes taxes & fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sleeps 4 · 1 bedroom
8.48.4 out of 10
Very goodvery good
314 reviews(314 reviews)
The current price is AU$1,335
AU$1,335
for 3 nights, 1 room
AU$445 per night
includes taxes & fees
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
8.28.2 out of 10
Very goodvery good
109 reviews(109 reviews)
The current price is AU$734
AU$734
for 3 nights, 1 room
AU$245 per night
includes taxes & fees
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