Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Save 100% on your flight
Price was $809, price is now $398 per person
$398
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago
Price was $1,104, price is now $517 per person
$517
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town
Price was $937, price is now $461 per person
$461
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Price was $1,185, price is now $590 per person
$590
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Level Chicago - River North
Price was $1,019, price is now $539 per person
$539
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Blackstone, Autograph Collection
Save 100% on your flight
Price was $758, price is now $408 per person
$408
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Price was $1,665, price is now $898 per person
$898
per person
Jan 16 - Jan 23
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Royal Sonesta Chicago River North
Save 100% on your flight
Price was $781, price is now $441 per person
$441
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sleepy Hollow Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Sleepy Hollow Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Nov 13 - Mon, Nov 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Thu, Nov 13 - Mon, Nov 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
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