Holiday rentals near 360 CHICAGO
We found 3,511 holiday rentals — enter your dates for availability
Take a look at private holiday rentals within easy reach of 360 CHICAGO that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include cable TV and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - 360 CHICAGO
Showing deals for:26 Sept - 3 Oct
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
10% off
Price is AU$7,388
AU$7,388
AU$1,055 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(64 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is AU$2,270
AU$2,270
AU$324 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
6% off
Price is AU$2,143
AU$2,143
AU$306 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$7,137
AU$7,137
AU$1,020 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 AU$3,887
AU$3,887
AU$555 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$3,284
AU$3,284
AU$469 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 AU$7,314
AU$7,314
AU$1,045 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$4,862
AU$4,862
AU$695 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse North - Pool - Gold Coast
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Luxury Designer Penthouse North - Pool - Gold Coast
Chicago, Illinois
8% off
Price is AU$9,120
AU$9,120
AU$1,303 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
7% off
Price is AU$9,078
AU$9,078
AU$1,297 per night
includes taxes & fees
Image gallery for Spacious 3 bedroom in ideal Roscoe village location
1010 out of 10 rating
Exceptional
(44 reviews)
Spacious 3 bedroom in ideal Roscoe village location
Chicago, IL
7% off
Price is AU$2,916
AU$2,916
AU$417 per night
includes taxes & fees
Image gallery for Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
Chicago, IL
7% off
Price is AU$9,065
AU$9,065
AU$1,295 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 2
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Beautiful Unit CHI in Prime River North - 2
Chicago, Illinois
15% off
Price is AU$5,955
AU$5,955
AU$851 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$5,439
AU$5,439
AU$777 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Kasa | Family Friendly 3 BD + Fast Wifi | Chicago
Chicago, Illinois
8% off
Price is AU$9,375
AU$9,375
AU$1,339 per night
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
8.88.8 out of 10 rating
Excellent
(5 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
7% off
Price is AU$2,045
AU$2,045
AU$292 per night
includes taxes & fees
Image gallery for Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Spacious, Sunny and Clean Apartment 25 min from Downtown Chicago
Berwyn, IL
8% off
Price is AU$2,274
AU$2,274
AU$325 per night
includes taxes & fees
Image gallery for Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
1010 out of 10 rating
Exceptional
(11 reviews)
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Chicago, IL
7% off
Price is AU$4,816
AU$4,816
AU$688 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 AU$5,821
AU$5,821
AU$832 per night
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.48.4 out of 10 rating
Very good
(10 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
7% off
Price is AU$2,764
AU$2,764
AU$395 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(25 reviews)
Experience Chicago living near United Center
Chicago, IL
7% off
Price is AU$2,053
AU$2,053
AU$293 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
32% off
Price is AU$4,587
AU$4,587
AU$655 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 AU$5,659
AU$5,659
AU$808 per night
includes taxes & fees
Image gallery for Chic 4-Bedroom Haven: Designer's Dream Home
1010 out of 10 rating
Exceptional
(5 reviews)
Chic 4-Bedroom Haven: Designer's Dream Home
Chicago, Illinois
12% off
Price is AU$6,306
AU$6,306
AU$901 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - 360 CHICAGO
Chic 1-bedroom apartment,15mims from downtown
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Sonder by Marriott Bonvoy The Opal Apartments River North
Sleeps 6 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
40 reviews(40 reviews)
Amazing Location 3BR Gem in Logan Square w Parking
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Sleeps 5 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Making The Best Memories Along The Way! Free Breakfast, Pets Allowed
Sleeps 5 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3 reviews(3 reviews)
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 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