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South Side Vacation Packages

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South Side Flight + Hotel Packages

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
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Burlington (BTV) 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.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Stay at this 4-star 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
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) 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.
The Maverick by Kasa

The Maverick by Kasa

3 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) 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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Burlington (BTV) 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.
City Sights 2 Queen Beds Downtown Apt

City Sights 2 Queen Beds Downtown Apt

2 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Stay at this apartment in Pittsburgh. Popular attractions PPG Paints Arena and PNC Park are located nearby.
2 Bedroom 2 Bathroom The Heart of Pittsburgh

2 Bedroom 2 Bathroom The Heart of Pittsburgh

2 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Stay at this apartment in Pittsburgh. Popular attractions PPG Paints Arena and PNC Park are located nearby.
2 Bedroom 2 Bath City Views

2 Bedroom 2 Bath City Views

2 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Stay at this apartment in Pittsburgh. Popular attractions PPG Paints Arena and PNC Park are located nearby.

South Side Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Pittsburgh Airport

Hilton Garden Inn Pittsburgh Airport

3 out of 5
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) 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
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) to Pittsburgh (PIT)
Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Oct 24 - Oct 27
found 12 hours ago
Roundtrip flight included
New York (JFK) 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, Oct 2 - Thu, Oct 16
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$70 Roundtrip, found 3 hours ago
$70
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Thu, Oct 2 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Thu, Oct 16, priced at $70 found 3 hours ago
Spirit Airlines
Wed, Oct 8 - Sat, Oct 11
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Oct 8 from Logan Intl. to Pittsburgh Intl., returning Sat, Oct 11, priced at $120 found 1 day ago
JetBlue Airways
Fri, Oct 31 - Fri, Nov 7
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 2 days ago
$121
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Oct 31 from John F. Kennedy Intl. to Pittsburgh Intl., returning Fri, Nov 7, priced at $121 found 2 days ago
Frontier Airlines
Mon, Sep 1 - Mon, Sep 8
PHL
Philadelphia Intl.
PIT
Pittsburgh Intl.
$129 Roundtrip, found 20 hours ago
$129
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Mon, Sep 1 from Philadelphia Intl. to Pittsburgh Intl., returning Mon, Sep 8, priced at $129 found 20 hours ago