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Holiday rentals near South Wentworth Street
We found 2,947 holiday rentals — enter your dates for availability
If you are looking to stay near South Wentworth Street, take a look at holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, such as parking and air conditioning. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - South Wentworth Street
Showing deals for:3 Oct - 10 Oct
Image gallery for Beautiful Downtown 3BR with Free Parking

9.69.6 out of 10 rating
Exceptional
(18 reviews)
Beautiful Downtown 3BR with Free Parking
Chicago, IL
7% off
Price is NZ$9,227
NZ$9,227
NZ$1,318 per night
includes taxes & fees
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
7% off
Price is NZ$14,140
NZ$14,140
NZ$2,020 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$9,049
NZ$9,049
NZ$1,293 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago

1010 out of 10 rating
Exceptional
(39 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$7,058
NZ$7,058
NZ$1,008 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access

1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is NZ$6,715
NZ$6,715
NZ$959 per night
includes taxes & fees
Image gallery for Kasa | Relaxing Studio + Pet Friendly | Chicago

9.89.8 out of 10 rating
Exceptional
(7 reviews)
Kasa | Relaxing Studio + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$4,421
NZ$4,421
NZ$632 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
8% off
Price is NZ$11,323
NZ$11,323
NZ$1,618 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$4,041
NZ$4,041
NZ$577 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 NZ$14,868
NZ$14,868
NZ$2,124 per night
includes taxes & fees
Image gallery for Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige

1010 out of 10 rating
Exceptional
(16 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Chicago, IL
7% off
Price is NZ$11,465
NZ$11,465
NZ$1,638 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck

9.69.6 out of 10 rating
Exceptional
(54 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,620
NZ$6,620
NZ$946 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
7% off
Price is NZ$12,110
NZ$12,110
NZ$1,730 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$6,817
NZ$6,817
NZ$974 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 NZ$6,379
NZ$6,379
NZ$911 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is NZ$12,066
NZ$12,066
NZ$1,724 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$6,849
NZ$6,849
NZ$978 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views

9.49.4 out of 10 rating
Exceptional
(14 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$7,975
NZ$7,975
NZ$1,139 per night
includes taxes & fees
Image gallery for 5 Star Upscale Entire Family Neighborhood Home

9.89.8 out of 10 rating
Exceptional
(27 reviews)
5 Star Upscale Entire Family Neighborhood Home
Berwyn, IL
8% off
Price is NZ$4,168
NZ$4,168
NZ$595 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 NZ$2,978
NZ$2,978
NZ$425 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$2,817
NZ$2,817
NZ$402 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$4,075
NZ$4,075
NZ$582 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$9,652
NZ$9,652
NZ$1,379 per night
includes taxes & fees
Image gallery for Lakefront property , minutes from McCormick Place and Downtown Chicago.

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Lakefront property , minutes from McCormick Place and Downtown Chicago.
Chicago, IL
11% off
Price is NZ$6,929
NZ$6,929
NZ$990 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field

9.49.4 out of 10 rating
Exceptional
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is NZ$3,225
NZ$3,225
NZ$461 per night
includes taxes & fees
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Find properties near top attractions in South Wentworth Street
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Find the best place to stay - South Wentworth Street
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
322 reviews(322 reviews)
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)
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
435 reviews(435 reviews)
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)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
805 reviews(805 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
8.28.2 out of 10
Very goodvery good
108 reviews(108 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