
Sleepy Hollow Holidays
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Our guide on where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Our pick of the best Sleepy Hollow Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$263 per night from 14 Feb to 15 Feb
NZ$263
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,821 reviews)
Yes perfectly clean
Reviewed on 24 Jan 2026

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$206 per night from 5 Feb to 6 Feb
NZ$206
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,614 reviews)
Too few elevators working…
Reviewed on 28 Jan 2026

DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$166 per night from 3 Feb to 4 Feb
NZ$166
3 Feb - 4 Feb
includes taxes & fees
8.6/10 Excellent! (2,266 reviews)
Great
Reviewed on 27 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Discover the most popular places to visit in Sleepy Hollow

Wrigley Field
4.5/5(21 reviews)
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

McCormick Place
4.5/5(21 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Navy Pier
4.5/5(64 reviews)
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.
Activities

Chicago: Navy Pier Centennial Wheel Ticket
NZ$43
per adult
88% of travellers recommend

Chicago Crime and Mob Bus Tour
NZ$85
per adult
92% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




