Chester Flight + Hotel Packages

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

Joinery Hotel Pittsburgh, Curio Collection by Hilton

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

The Maverick by Kasa

Save 100% on your flight

per person

Jun 30 - Jul 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Pittsburgh (PIT)

Stay at this 3-star hotel in Pittsburgh. Enjoy free WiFi, a 24-hour business center, and cable TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Homewood Suites by Hilton Pittsburgh Downtown

Save 100% on your flight

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

Stay at this 3-star 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 PPG Paints Arena and PNC Park are located nearby.

Kimpton Hotel Monaco Pittsburgh by IHG

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

Stay at this 4.5-star luxury hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Hampton Inn & Suites Cranberry Pittsburgh

per person

Jul 2 - Jul 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

Book a stay at this business-friendly hotel in Cranberry Township. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions UPMC Lemieux Sports Complex and Seven Fields Nature Preserve are located nearby.

Placemakr Downtown Pittsburgh

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

Stay at this 3-star apartment in Pittsburgh. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Seven Springs Resort Properties

per person

Aug 22 - Aug 25

found 20 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Pittsburgh (PIT)

Stay at this 4-star spa aparthotel in Champion. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Seven Springs Mountain Resort and Alpine Slide are located nearby.

Wyndham Grand Pittsburgh Downtown

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms 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.

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

Homewood Suites by Hilton Pittsburgh Downtown

Downtown Pittsburgh

Save 100% on your flight

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

Kimpton Hotel Monaco Pittsburgh by IHG

Downtown Pittsburgh

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

Placemakr Downtown Pittsburgh

Downtown Pittsburgh

per person

Jul 31 - Aug 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

Chester Vacation Packages 5-7 Night Stays

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

Hampton Inn & Suites Cranberry Pittsburgh

per person

Jul 2 - Jul 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)