Vacation rentals in Chicago Loop

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Top-rated vacation rentals in Chicago Loop

Guests agree: these stays are highly rated for location, cleanliness, and more.

Rental unit in The Loop
Lovely 1-bedroom serviced apartment near Museums!
Modern 1-bd loft space in Chicago's South Loop. This unique apartment offers comfortable sleeping arrangements, lots of space to relax plus a desk to work. The building is a renovated Chicago Post Office with great history! You'll be steps away from Grant Park, many fantastic local restaurants, bars, and shopping options. Enjoy a walk around Historic Printer's Row, get some work done with high-speed WiFi or cozy up and watch Netflix! Our apartment has everything you'll need to enjoy Chicago!
$95 per night
Rental unit in The Loop
*Luxury High Rise, Clean Design/Balcony/Amenities!
This brand new listing is a modern 1bedroom apartment it is placed in the heart of downtown where Chicago’s most desired attractions are within one mile . It boasts a minimal sophisticated design and wonderful views of downtown architecture. There is an in unit washer and dryer and a number of amenities including rooftop deck, gym, work spaces and lounge. Within 500 feet there are a number of bars, restaurants, and even a grocery store. You get a luxury experience with a neighborhood feel!
$150 per night
Private room in River North
Chicago Speakeasy-Style Loft Space (Room 1A)
Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with a lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings! Feel free to message me!
$100 per night
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Stay near Chicago Loop's top sights

Photo of Millennium Park
Millennium Park1,244 locals recommend
Photo of Cloud Gate
Cloud Gate473 locals recommend
Photo of Willis Tower
Willis Tower324 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago1,159 locals recommend
Photo of Skydeck Chicago
Skydeck Chicago124 locals recommend
Photo of Buckingham Fountain
Buckingham Fountain219 locals recommend

Other great vacation rentals in Chicago Loop

Condo in Little Italy
Private hot tub and king bed suite
$116 per night
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Rental unit in The Loop
Entire Studio Apartment | View of Millennium Park
$126 per night
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Rental unit in The Loop
Great View @TheLoop steps to MilleniumPark✭
$134 per night
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Private room in The Loop
Downtown/Lake/Soldier Field Paradise Haven
$109 per night
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Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
$87 per night
Condo in The Loop
Downtown Park #11 - Mich Ave PH | gym+rooftop
$119 per night
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Condo in The Loop
Premiere Downtown Location! River Walk & Mag Mile
$161 per night
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Rental unit in The Loop
The Glowing Getaway (2BR)
$122 per night
Private room in Little Italy
Beautiful Private Room 5 min to downtown Chicago
$64 per night
Hotel room in The Loop
King Room in Downtown
$103 per night
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Rental unit in West Loop
1-bedroom rental with a great view!
$108 per night
Rental unit in The Loop
Cozy 1 BR Apartment in South Loop
$96 per night
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