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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $576, price is now $369 per person
$369
per person
Jun 22 - Jun 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $807, price is now $425 per person
$425
per person
Jun 22 - Jun 25
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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $818, price is now $487 per person
$487
per person
Jun 12 - Jun 15
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 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park 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 $906, price is now $547 per person
$547
per person
Jun 27 - Jun 30
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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
Price was $829, price is now $507 per person
$507
per person
Jun 22 - Jun 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,055, price is now $686 per person
$686
per person
Jun 22 - Jun 25
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, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $661, price is now $439 per person
$439
per person
Jun 22 - Jun 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
Save 100% on your flight
Price was $554, price is now $372 per person
$372
per person
Jun 16 - Jun 20
found 19 hours 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 fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall 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
Save 100% on your flight
Price was $807, price is now $425 per person
$425
per person
Jun 22 - Jun 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $818, price is now $487 per person
$487
per person
Jun 12 - Jun 15
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 $906, price is now $547 per person
$547
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $829, price is now $507 per person
$507
per person
Jun 22 - Jun 25
found 1 day 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,322, price is now $633 per person
$633
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,625, price is now $937 per person
$937
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,630, price is now $960 per person
$960
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,395, price is now $846 per person
$846
per person
Jun 11 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Sat, Apr 25 - Sat, May 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 6 days ago
$101
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 2, priced at $101 found 6 days ago
ITA Airways
Sun, Jul 12 - Tue, Jul 21
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$893 Roundtrip, found 10 hours ago
$893
Roundtrip
found 10 hours ago
Select ITA Airways flight, departing Sun, Jul 12 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Jul 21, priced at $893 found 10 hours ago
Etihad Airways
Sat, Jun 6 - Thu, Jun 18
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,056 Roundtrip, found 2 days ago
$1,056
Roundtrip
found 2 days ago
Select Etihad Airways flight, departing Sat, Jun 6 from Pudong Intl. to O'Hare Intl., returning Thu, Jun 18, priced at $1,056 found 2 days ago
All Nippon Airways
Thu, Apr 16 - Wed, Apr 29
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,235 Roundtrip, found 14 hours ago
$1,235
Roundtrip
found 14 hours ago
Select All Nippon Airways flight, departing Thu, Apr 16 from Hong Kong Intl. to O'Hare Intl., returning Wed, Apr 29, priced at $1,235 found 14 hours ago