Holiday rentals near 360 CHICAGO
We found 3,510 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 NZ$7,937
NZ$7,937
NZ$1,134 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 NZ$2,426
NZ$2,426
NZ$347 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 NZ$2,288
NZ$2,288
NZ$327 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$7,687
NZ$7,687
NZ$1,098 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 NZ$4,205
NZ$4,205
NZ$601 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 NZ$3,554
NZ$3,554
NZ$508 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 NZ$7,914
NZ$7,914
NZ$1,131 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$6,120
NZ$6,120
NZ$874 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 NZ$5,258
NZ$5,258
NZ$751 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 NZ$9,788
NZ$9,788
NZ$1,398 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 NZ$9,822
NZ$9,822
NZ$1,403 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 NZ$3,155
NZ$3,155
NZ$451 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 NZ$9,738
NZ$9,738
NZ$1,391 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 NZ$6,440
NZ$6,440
NZ$920 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 NZ$5,868
NZ$5,868
NZ$838 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 NZ$2,215
NZ$2,215
NZ$316 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 NZ$2,432
NZ$2,432
NZ$347 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 NZ$5,208
NZ$5,208
NZ$744 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 NZ$6,294
NZ$6,294
NZ$899 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 NZ$2,958
NZ$2,958
NZ$423 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 NZ$2,183
NZ$2,183
NZ$312 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 NZ$4,959
NZ$4,959
NZ$708 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 NZ$6,120
NZ$6,120
NZ$874 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 NZ$6,824
NZ$6,824
NZ$975 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
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