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Sleepy Hollow Vacations from ￥340,687

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The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 25 - Aug 29

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.2/10 - Very Good (2,839 reviews)
    "Don’t expect a full service hotel, but it is suitably located, the staff couldn’t have been nicer, it was clean, and again, I can’t say enough about staff friendliness. Our room was tiny, so if you intend to spend a lot of time in the room, keep that in mind. But, we were out and about and enjoyed our stay very much!"
    Reviewed July 16, 2026
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥413,758
    ￥340,687
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Terrace/patio
    Aug 25 - Aug 29

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,588 reviews)
    "The scenery from the room was unmatched"
    Reviewed July 16, 2026
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥520,328
    ￥420,151
    per traveler
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-size fridge, microwave, oven, stovetop
    Aug 25 - Aug 29

    Level Chicago – Old Town + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.0/10 - Wonderful (501 reviews)
    "Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."
    Reviewed July 14, 2026
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥467,275
    ￥379,566
    per traveler
    found 23 hours ago
    Level Chicago – Old Town
  • Terrace/patio
    Aug 25 - Aug 29

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,938 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥516,278
    ￥430,769
    per traveler
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Aug 25 - Aug 29

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,757 reviews)
    Roundtrip • Tokyo (TYO) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥457,188
    ￥381,469
    per traveler
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

Sleepy Hollow Hotel Deals

Free daily continental breakfast

Elgin Inn

Elgin Inn
3.0 star property
3.3 km from Sleepy Hollow
8.0 out of 10, Very Good, (784 reviews)
The price is ￥13,618
￥15,521 total
includes taxes & fees
Jul 20 - Jul 21
Elgin Inn
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.
See all properties in Sleepy Hollow
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.