
Sleepy Hollow Vacation Packages
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Top Holiday Package Deals in Sleepy Hollow
Price found within the past 48 hours. Click for updated prices.

The Royal Sonesta Chicago River North
Downtown Chicago
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
so I gotta say The royal sonesta river north in particular is amazing it feels more like a hotel, it feels like a small community and all the staff and guest know each other. The front desk woman Gabby is amazing and dope as heck. Shaunda is a travel guide there, shes hilarious and gave us wonderful recommendations in the area. Antwonne is a dope Bellman great service and attitude. Every detail was perfect Jessenia apart of the housekeeping staff has such good attention to detail when it came to fixing up and cleaning the room everything was so organized and neat. Now to the room it couldn't have been more perfect they upgraded us to the luxury suite and it was beautiful (use the tub as much as you can)
Reviewed on Aug. 15, 2025



Level Chicago - River North
Downtown Chicago
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything. We stayed at Fultom before and the River North is really good as well. Only difference slighty better views with sky terrace at Fulton and from pool side and indoor spa. Riverside has game room which my kid and I enjoyed tons of chess. Great place hard to pick one both has pros and really no cons. Look forward to our next stay. Higher floor the better witb views from the room. Great staff as well!
Reviewed on Aug. 15, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.
Reviewed on Aug. 17, 2025
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.
Sleepy Hollow Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Aug 18 to Aug 19
CA $177
CA $207 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,916 reviews)
"Great views of the lake. Good location for museum campus and northerly island."
Reviewed on Aug. 14, 2025

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Sep 1 to Sep 2
CA $209
CA $245 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,184 reviews)
"Very nice place close to so many places."
Reviewed on Aug. 15, 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Aug 24 to Aug 25
CA $222
CA $261 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (4,711 reviews)
"Happy Hour drinks were amazing!"
Reviewed on Aug. 16, 2025
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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Chicago By Night River & Lake Cruise
CA $62
per adult
96% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
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Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.