Search Deals onSleepy Hollow Vacation Packages
Sleepy Hollow Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Arlo Chicago
Save 100% on your flight
Price was $386, price is now $276 per person
$276
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

La Banque Hotel
Save 100% on your flight
Price was $667, price is now $403 per person
$403
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $638, price is now $398 per person
$398
per person
Apr 4 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town
Save 100% on your flight
Price was $1,567, price is now $987 per person
$987
per person
Apr 4 - Apr 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.

Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $988, price is now $649 per person
$649
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.

Courtyard by Marriott Chicago Magnificent Mile
Save 100% on your flight
Price was $428, price is now $289 per person
$289
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.

Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $590, price is now $406 per person
$406
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.

Hilton Chicago
Save 100% on your flight
Price was $448, price is now $314 per person
$314
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field 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.

Tue, Mar 24 - Wed, Mar 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 13 hours ago
$108
Roundtrip
found 13 hours ago

Tue, Apr 28 - Wed, May 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 23 hours ago
$179
Roundtrip
found 23 hours ago

Thu, Jan 29 - Tue, Feb 3
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$572 Roundtrip, found 5 days ago
$572
Roundtrip
found 5 days ago

Sat, Feb 28 - Mon, Mar 16
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,154 Roundtrip, found 5 hours ago
$1,154
Roundtrip
found 5 hours ago
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