Chicago Grayland Station holiday rentals
We found 3,726 holiday rentals — enter your dates for availability
Find the perfect private holiday rental that's close to Chicago Grayland Station. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as air conditioning and a pool. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Chicago Grayland Station
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$13,537
AU$13,537
AU$1,934 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$11,076
AU$11,076
AU$1,582 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$6,176
AU$6,176
AU$882 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$9,609
AU$9,609
AU$1,373 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$14,501
AU$14,501
AU$2,072 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$12,481
AU$12,481
AU$1,783 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$3,599
AU$3,599
AU$514 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$2,893
AU$2,893
AU$413 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$3,417
AU$3,417
AU$488 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$14,443
AU$14,443
AU$2,063 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 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$5,808
AU$5,808
AU$830 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$6,981
AU$6,981
AU$997 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$12,684
AU$12,684
AU$1,812 per night
includes taxes & fees
Image gallery for NEW Contemporary Home - 5BR/3.5BA+office+garage
9.29.2 out of 10 rating
Wonderful
(12 reviews)
NEW Contemporary Home - 5BR/3.5BA+office+garage
Chicago, IL
7% off
Price is AU$9,647
AU$9,647
AU$1,378 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 02 - Terrace - River North
1010 out of 10 rating
Exceptional
(19 reviews)
Luxury Loft Collection 02 - Terrace - River North
Chicago, IL
8% off
Price is AU$14,047
AU$14,047
AU$2,007 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$7,175
AU$7,175
AU$1,025 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$12,835
AU$12,835
AU$1,834 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Chicago, IL
7% off
Price is AU$4,198
AU$4,198
AU$600 per night
includes taxes & fees
Image gallery for Cozy 2BR/1BA Garden Apartment Near Lincoln Square
8.28.2 out of 10 rating
Very good
(10 reviews)
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Chicago, IL
6% off
Price is AU$2,872
AU$2,872
AU$410 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Chicago Grayland Station
Showing deals for: 4 Oct - 7 Oct
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
323 reviews(323 reviews)
The current price is AU$1,440
AU$1,440
for 3 nights, 1 room
AU$480 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$1,393
AU$1,393
for 3 nights, 1 room
AU$464 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$1,735
AU$1,735
for 3 nights, 1 room
AU$578 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$1,548
AU$1,548
for 3 nights, 1 room
AU$516 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$1,344
AU$1,344
for 3 nights, 1 room
AU$448 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$1,150
AU$1,150
for 3 nights, 1 room
AU$383 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