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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 $931, price is now $582 per person
$582
per person
Jun 10 - Jun 15
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
Price was $1,692, price is now $846 per person
$846
per person
Jun 10 - Jun 15
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.
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 $1,618, price is now $982 per person
$982
per person
Jun 10 - Jun 15
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,254, price is now $789 per person
$789
per person
Jun 10 - 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 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $2,115, price is now $1,337 per person
$1,337
per person
Jul 22 - Jul 27
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 a fitness center. Our guests praise the helpful staff in our reviews. 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 $1,612, price is now $1,021 per person
$1,021
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $957, price is now $613 per person
$613
per person
Jul 3 - Jul 7
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,121, price is now $727 per person
$727
per person
Jun 10 - Jun 15
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.

Sleepy Hollow Vacation Packages 3-4 Night Stays

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
Downtown Chicago
Save 100% on your flight
Price was $954, price is now $595 per person
$595
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,093, price is now $602 per person
$602
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,345, price is now $776 per person
$776
per person
Jul 29 - Aug 1
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 $1,194, price is now $739 per person
$739
per person
Jul 29 - Aug 1
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,262, price is now $695 per person
$695
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,692, price is now $846 per person
$846
per person
Jun 10 - Jun 15
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 $1,508, price is now $893 per person
$893
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,589, price is now $945 per person
$945
per person
Jun 10 - Jun 16
found 8 hours 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
Mon, Jun 8 - Fri, Jun 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jun 8 from Los Angeles Intl. to O'Hare Intl., returning Fri, Jun 19, priced at $172 found 4 days ago
Turkish Airlines
Wed, Jul 8 - Wed, Jul 22
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$749 Roundtrip, found 16 hours ago
$749
Roundtrip
found 16 hours ago
Select Turkish Airlines flight, departing Wed, Jul 8 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Wed, Jul 22, priced at $749 found 16 hours ago
Delta
Tue, Jun 2 - Mon, Sep 7
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,165 Roundtrip, found 1 day ago
$1,165
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 2 from Pudong Intl. to O'Hare Intl., returning Mon, Sep 7, priced at $1,165 found 1 day ago
Japan Airlines
Tue, Jun 2 - Mon, Sep 7
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$1,481 Roundtrip, found 3 days ago
$1,481
Roundtrip
found 3 days ago
Select Japan Airlines flight, departing Tue, Jun 2 from Hongqiao Intl. to O'Hare Intl., returning Mon, Sep 7, priced at $1,481 found 3 days ago