Sleepy Hollow Packages (Flight + Hotel)
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Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
21 Aug - 23 Aug
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The property and room was nicely decorated. The beautiful aids were nice. Rooms are small no dresser to put your things in. I called and asked about a having access to a refrigerator. I was told that there was not one in the my room and that I could get one apron request for 20 dollars. When I checked in I requested a refrigerator and was told there was not one available or I could upgrade my room that included one for 17 dollars a night. I brought with me parishable food items because I was on a budget. Half of my food items went to waist and I could not store my left overs. Needless to say I was disappointed. The staff were helpful, nice and courteous.
Reviewed on 9 Jul 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
21 Aug - 23 Aug
found 4 hours ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
WE LIKE CLEANLINESS & CHILDREN MUSEUM AND AROUND THE HOTEL
Reviewed on 8 Jul 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.
Top hotels in Sleepy Hollow
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,783 per night from 4 Aug to 5 Aug
฿5,783
฿6,789 total
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,930 reviews)
"Good location.good staff."
Reviewed on 9 Jul 2025
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ฿7,277 per night from 24 Jul to 25 Jul
฿7,277
฿9,586 total
24 Jul - 25 Jul
includes taxes & fees
9/10 Wonderful! (2,009 reviews)
"We had a wonderful stay at the Intercontinental Magnificent Mile over the July 4th weekend! We enjoyed all 3 restaurants/bars- especially Casa Chi! The staff were all excellent. The spot is super convenient/walkable to everywhere you would want to go in downtown Chicago, a block from the riverwalk ..."
Reviewed on 9 Jul 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is ฿5,293 per night from 10 Aug to 11 Aug
฿5,293
฿6,214 total
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,430 reviews)
"I always prefer staying in Hilton!"
Reviewed on 12 Jul 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
Popular places to visit
Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(147 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
฿4,634
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.