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Sleepy Hollow Vacation Packages

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Sleepy Hollow Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $958, price is now $510 per person
$510
per person
Feb 14 - 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,198, price is now $661 per person
$661
per person
Feb 14 - Feb 22
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $1,347, price is now $744 per person
$744
per person
Feb 14 - 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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $923, price is now $523 per person
$523
per person
Feb 14 - 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.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $999, price is now $575 per person
$575
per person
Feb 14 - Feb 22
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $950, price is now $550 per person
$550
per person
Feb 26 - Mar 1
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.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $974, price is now $567 per person
$567
per person
Feb 14 - 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, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $955, price is now $569 per person
$569
per person
Feb 14 - 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 full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Sleepy Hollow Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $432, price is now $255 per person
$255
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $650, price is now $365 per person
$365
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $950, price is now $550 per person
$550
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $549, price is now $329 per person
$329
per person
Mar 7 - Mar 10
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Sleepy Hollow Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $892, price is now $502 per person
$502
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,220, price is now $638 per person
$638
per person
Jan 26 - Feb 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,135, price is now $631 per person
$631
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $927, price is now $528 per person
$528
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Feb 10 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 18, priced at $163 found 1 day ago
United
Sat, Jan 17 - Sun, Jan 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 17 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jan 18, priced at $163 found 1 day ago
American Airlines
Sat, Feb 14 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Feb 14 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 18, priced at $163 found 2 days ago
Turkish Airlines
Sat, Feb 28 - Mon, Mar 16
PVG
Pudong Intl.
ORD
O'Hare Intl.
$950 Roundtrip, found 2 days ago
$950
Roundtrip
found 2 days ago
Select Turkish Airlines flight, departing Sat, Feb 28 from Pudong Intl. to O'Hare Intl., returning Mon, Mar 16, priced at $950 found 2 days ago