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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Price was $676, price is now $508 per person
$508
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Price was $1,309, price is now $875 per person
$875
per person
May 22 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Save 100% on your flight
Price was $985, price is now $705 per person
$705
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Stay at this apartment in Pittsburgh. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Popular attractions PPG Paints Arena and PNC Park are located nearby.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Price was $790, price is now $572 per person
$572
per person
May 22 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this aparthotel in Pittsburgh. Enjoy free WiFi, laundry facilities, and satellite TV channels. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Price was $1,068, price is now $823 per person
$823
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free WiFi, a rooftop terrace, and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Price was $793, price is now $613 per person
$613
per person
Jul 3 - Jul 5
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. 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 PPG Paints Arena and PNC Park are located nearby.
The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Price was $1,131, price is now $876 per person
$876
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Stay at this vacation home in Pittsburgh. Enjoy free WiFi, a free airport shuttle, and a garden. Popular attractions Acrisure Stadium and PNC Park are located nearby.
Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
Price was $755, price is now $587 per person
$587
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $739, price is now $412 per person
$412
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,025, price is now $698 per person
$698
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $985, price is now $705 per person
$705
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $837, price is now $600 per person
$600
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,058, price is now $595 per person
$595
per person
Jun 9 - Jun 14
just found
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,257, price is now $878 per person
$878
per person
Jun 9 - Jun 14
just found
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was $1,785, price is now $1,320 per person
$1,320
per person
Jun 7 - Jun 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
Central Oakland
Price was $1,046, price is now $797 per person
$797
per person
Jun 9 - Jun 14
just found
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)

Top Flight Deals

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

Delta
Tue, Jun 9 - Tue, Jun 16
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$157 Roundtrip, found 8 hours ago
$157
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Jun 9 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Tue, Jun 16, priced at $157 found 8 hours ago
Delta
Fri, May 29 - Mon, Jun 1
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$161 Roundtrip, found 1 hour ago
$161
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, May 29 from John F. Kennedy Intl. to Pittsburgh Intl., returning Mon, Jun 1, priced at $161 found 1 hour ago
Delta
Mon, Jun 1 - Fri, Jun 19
LGA
LaGuardia
PIT
Pittsburgh Intl.
$171 Roundtrip, found 20 hours ago
$171
Roundtrip
found 20 hours ago
Select Delta flight, departing Mon, Jun 1 from LaGuardia to Pittsburgh Intl., returning Fri, Jun 19, priced at $171 found 20 hours ago
Frontier Airlines
Sat, Apr 25 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 25 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Sat, May 2, priced at $173 found 1 day ago