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The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Congress Plaza Hotel
Downtown Chicago
Price was NT$61,649, price is now NT$50,889 per person
NT$50,889
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
8/10 Very Good! (9,193 reviews)
Great location and because it’s an old hotel it’s quiet. Could use a bathroom upgrade toilet is very low.
Reviewed on 2025/10/6

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NT$80,562, price is now NT$60,461 per person
NT$60,461
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on 2025/9/26

The Peninsula Chicago
Downtown Chicago
Price was NT$135,234, price is now NT$106,358 per person
NT$106,358
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Excellent hotel, my only complaint would be the Peninsula food service.
We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster.
As to the main dining room the service continues, as always, to be erratic and frequently slow. Food is sometimes served hot, sometimes not.
The room service on our checkout day was absolutely abysmal. We both ordered eggs Benedict and both orders were served not a degree above room temperature. The hollandaise sauce was so cold it had solidified.
There really is no excuse for this.
And unfortunately we did not have time to return the order as we had a plane to catch and we were running a bit behind.
For an otherwise professional hotel the food service and quality is sadly lacking. It leads one to believe that the F&B manager could be a nephew, a cousin, or some other family member need of a job.
Reviewed on 2025/9/27

Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was NT$70,784, price is now NT$57,999 per person
NT$57,999
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
8.4/10 Very Good! (3,910 reviews)
I had a great stay at the Hilton! The staff were super friendly and welcoming — they even let us check in early, which was a huge plus. The location couldn’t have been better — it’s right across the street from a subway station, and there’s a grocery store and CVS just a short walk away. The area felt very safe and convenient. Overall, a wonderful experience — I’d definitely stay here again!
Reviewed on 2025/10/6

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was NT$71,979, price is now NT$59,239 per person
NT$59,239
per person
Nov 29 - Dec 5
found 1 hour ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
8.2/10 Very Good! (1,705 reviews)
Great location, however one of our windows in our room wouldn’t close all the way so it made it very loud being by the hospital. And if staying with someone, I hope you’re close because you can see straight to the toilet with the door shut! Otherwise, great location, friendly staff, clean.
Reviewed on 2025/10/5
Find the Best Sleepy Hollow Vacation Packages
Sleepy Hollow Hotel Deals

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 NT$2,964 per night from Oct 12 to Oct 13
NT$2,964
NT$3,289 total
Oct 12 - Oct 13
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"I can’t complain. I was only there one night but the place was really clean and spacious for what I paid."
Reviewed on 2025/10/4

Courtyard by Marriott Chicago Wood Dale
900 N Wood Dale Rd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is NT$2,814 per night from Oct 30 to Oct 31
NT$2,814
NT$3,123 total
Oct 30 - Oct 31
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Super helpful staff and very nice clean rooms! The shuttle to the airport is a great convenience when traveling to and from the airport."
Reviewed on 2025/9/29

Eaglewood Resort and Spa
1401 Nordic Rd, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is NT$3,119 per night from Oct 9 to Oct 10
NT$3,119
NT$4,130 total
Oct 9 - Oct 10
includes taxes & fees
8.6/10 Excellent! (1,046 reviews)
"This was an amazing stay."
Reviewed on 2025/10/1
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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