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South Side Vacation Packages

Build your package with 2 more options

South Side Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Suburban Studios Triadelphia - Wheeling at The Highlands

Suburban Studios Triadelphia - Wheeling at The Highlands

2 out of 5
Price was $304, price is now $234 per person
$234
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Triadelphia. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Oglebay Park and The Highlands are located nearby.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Price was $533, price is now $372 per person
$372
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
Price was $600, price is now $423 per person
$423
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
Book a stay at this 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.
Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Price was $730, price is now $545 per person
$545
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
Book a stay at this 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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Price was $525, price is now $393 per person
$393
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Microtel Inn & Suites by Wyndham Wheeling at Highlands

Microtel Inn & Suites by Wyndham Wheeling at Highlands

2 out of 5
Price was $364, price is now $278 per person
$278
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Triadelphia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oglebay Park and The Highlands are located nearby.
Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Price was $865, price is now $666 per person
$666
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
Book a stay at this luxury hotel in Pittsburgh. Enjoy a full-service spa, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PNC Park and PPG Paints Arena are located nearby.
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Price was $681, price is now $526 per person
$526
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.

South Side Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $533, price is now $372 per person
$372
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $600, price is now $423 per person
$423
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was $730, price is now $545 per person
$545
per person
Mar 4 - Mar 7
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $525, price is now $393 per person
$393
per person
Mar 4 - Mar 7
found 20 hours ago
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
Wed, Jan 28 - Thu, Feb 12
LGA
LaGuardia
PIT
Pittsburgh Intl.
$121 Roundtrip, found 22 hours ago
$121
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, Jan 28 from LaGuardia to Pittsburgh Intl., returning Thu, Feb 12, priced at $121 found 22 hours ago
American Airlines
Sat, Jan 31 - Sat, Feb 7
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jan 31 from John F. Kennedy Intl. to Pittsburgh Intl., returning Sat, Feb 7, priced at $121 found 1 day ago
United
Tue, Jan 20 - Tue, Jan 27
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$121 Roundtrip, found 22 hours ago
$121
Roundtrip
found 22 hours ago
Select United flight, departing Tue, Jan 20 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Tue, Jan 27, priced at $121 found 22 hours ago
Spirit Airlines
Sat, Feb 7 - Mon, Feb 9
ATL
Hartsfield-Jackson Atlanta Intl.
PIT
Pittsburgh Intl.
$123 Roundtrip, found 11 hours ago
$123
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Sat, Feb 7 from Hartsfield-Jackson Atlanta Intl. to Pittsburgh Intl., returning Mon, Feb 9, priced at $123 found 11 hours ago