Sleepy Hollow Holidays from AU$3,786
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Your Sleepy Hollow Holiday
History, cuisine, art and more … There's so much to discover with a Sleepy Hollow holiday package. And with the ability to customise your city getaway, you know it'll be one that's hard to forget. Ready to explore your surroundings? Grand Victoria Casino, Santas Village and NOW Arena are just a few of the top-rated places to visit during a trip to Sleepy Hollow. Whoever you're heading away with and whatever your budget, your ultimate Sleepy Hollow holiday is just a few clicks away with Expedia.
The Latest Sleepy Hollow Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was AU$4,948, price is now AU$3,786 per person
AU$3,786
per person
28 July - 4 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,368 reviews)
Excellent hotel and close to restaurants and shopping. Very clean.
Reviewed on 24 May 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$6,123, price is now AU$3,882 per person
AU$3,882
per person
28 July - 4 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
From the fitness center to the restaurant, all facilities are well maintained by staff and they were helpful with all requests.
Reviewed on 26 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$5,761, price is now AU$4,025 per person
AU$4,025
per person
28 July - 4 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Clean and have a beautiful view of the lake
Reviewed on 26 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$6,045, price is now AU$4,257 per person
AU$4,257
per person
28 July - 4 Aug
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Excellent location! Great views from our room.
Reviewed on 25 May 2026
Sleepy Hollow Holiday
Sleepy Hollow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 3,300 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Santas Village, Hemmens Cultural Centre and Main Beach |
Our pick of the best Sleepy Hollow Hotel Deals
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is AU$90 per night from 6 June to 7 June
AU$90
6 June - 7 June
includes taxes & fees
5.4/10 (1,007 reviews)
"True dump, staff very unpleasant, everything is dirty or broken. Great rate."
Reviewed on 25 May 2026
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 14 June to 15 June
AU$221
14 June - 15 June
includes taxes & fees
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 31 May to 1 June
AU$172
31 May - 1 June
includes taxes & fees
7.8/10 Good! (1,010 reviews)
"When we checkin the door key system was not working. So we did not had keys until next day. They let us in using their master keys. The light lamp was not working even after reporting at front desk no one camw to fixed it. We stayed for 2 nights. Therewas no hand soap in bathroom or in shower tub. ..."
Reviewed on 25 May 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
