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 $274, price is now $179 per person
$179
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $542, price is now $316 per person
$316
per person
Feb 6 - Feb 8
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $329, price is now $199 per person
$199
per person
Feb 20 - Feb 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Save 100% on your flight
Price was $437, price is now $265 per person
$265
per person
Feb 20 - Feb 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 United Center and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
Price was $630, price is now $383 per person
$383
per person
Feb 12 - Feb 16
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.
Chicago Athletic Association, a Hyatt Hotel
Save 100% on your flight
Price was $538, price is now $337 per person
$337
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $332, price is now $210 per person
$210
per person
Feb 20 - Feb 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 rooftop terrace, 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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $326, price is now $217 per person
$217
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff 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.
Fri, Dec 12 - Sun, Dec 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$143 Roundtrip, found 5 days ago
$143
Roundtrip
found 5 days ago
Sat, Jan 17 - Sun, Jan 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 5 days ago
$163
Roundtrip
found 5 days ago
Thu, Dec 11 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$782 Roundtrip, found 10 hours ago
$782
Roundtrip
found 10 hours ago
Thu, May 7 - Mon, May 18
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,169 Roundtrip, found 3 hours ago
$1,169
Roundtrip
found 3 hours ago
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