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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.
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Pittsburgh (PIT)
Stay at this 3-star business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, room service, 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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Stay at this 4-star 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.
Etage Executive Living

Etage Executive Living

3.5 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Stay at this 3.5-star 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.
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.
Springhill Suites by Marriott Pittsburgh Mt. Lebanon

Springhill Suites by Marriott Pittsburgh Mt. Lebanon

2 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Stay at this hotel in Pittsburgh. Enjoy free breakfast, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Acrisure Stadium and PPG Paints Arena are located nearby.
TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Stay at this 3-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Oct 24 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Pittsburgh (PIT)

Top Flight Deals

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

Spirit Airlines
Thu, Sep 4 - Thu, Sep 11
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$60 Roundtrip, found 8 hours ago
$60
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Thu, Sep 4 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Thu, Sep 11, priced at $60 found 8 hours ago
Spirit Airlines
Wed, Sep 17 - Tue, Sep 23
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$106 Roundtrip, found 3 days ago
$106
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Sep 17 from Logan Intl. to Pittsburgh Intl., returning Tue, Sep 23, priced at $106 found 3 days ago
JetBlue Airways
Wed, Oct 8 - Wed, Oct 15
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Oct 8 from John F. Kennedy Intl. to Pittsburgh Intl., returning Wed, Oct 15, priced at $121 found 1 day ago
Frontier Airlines
Thu, Aug 14 - Mon, Aug 18
PHL
Philadelphia Intl.
PIT
Pittsburgh Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Philadelphia Intl. to Pittsburgh Intl., returning Mon, Aug 18, priced at $127 found 1 day ago