
Sleepy Hollow Trip
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- Better togetherSave up to ₹100,000 when you book a flight and hotel together*
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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.
Top hotels in Sleepy Hollow

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹12,972 per night from 29 Jun to 30 Jun
₹12,972
₹15,423 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,282 reviews)
"The gentleman that checked me in was not friendly. Barely spoke to me at all. Did not really give me any info on where things were located or how to get to my room. Thankfully a kind staff member realized I was walking in circles and helped me out. I get to my room and the tv does not work unless ..."
Reviewed on 15 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is ₹13,730 per night from 30 Jun to 1 Jul
₹13,730
₹16,323 total
30 Jun - 1 Jul
includes taxes & fees
7.8/10 Good! (1,589 reviews)
"We were there just to sleep. Got there late at night. But the front desk was very helpful and kind. Felt bad she was all alone."
Reviewed on 15 Jun 2026

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ₹15,123 per night from 28 Jun to 29 Jun
₹15,123
₹17,237 total
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,672 reviews)
"The hotel itself is nice staff friendly but beware of parking costs and expensive breakfast buffet. Would stay again."
Reviewed on 14 Jun 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



