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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
Aug 1 - Aug 4
found 3 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
per person
Aug 1 - Aug 4
found 3 hours 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 Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Pittsburgh (PIT)
Stay at this 4-star 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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
per person
Aug 1 - Aug 4
found 3 hours 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.
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
per person
Aug 1 - Aug 4
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Book a stay at this business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Acrisure Stadium and PNC Park are located nearby.
Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

3 out of 5
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Hilton Garden Inn Pittsburgh University Place

Hilton Garden Inn Pittsburgh University Place

3 out of 5
per person
Aug 1 - Aug 4
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
Stay at this 3-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 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.

South Side 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
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Pittsburgh (PIT)
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Pittsburgh (PIT)
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Pittsburgh (PIT)
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Sep 11 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Pittsburgh (PIT)

Top Flight Deals

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

Spirit Airlines
Fri, Oct 3 - Sun, Oct 19
EWR
Newark Liberty Intl. Airport
PIT
Pittsburgh Intl.
$65 Roundtrip, found 7 hours ago
$65
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Fri, Oct 3 from Newark Liberty Intl. Airport to Pittsburgh Intl., returning Sun, Oct 19, priced at $65 found 7 hours ago
Frontier Airlines
Thu, Jul 10 - Mon, Jul 14
PHL
Philadelphia Intl.
PIT
Pittsburgh Intl.
$88 Roundtrip, found 11 hours ago
$88
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Jul 10 from Philadelphia Intl. to Pittsburgh Intl., returning Mon, Jul 14, priced at $88 found 11 hours ago
Spirit Airlines
Mon, Jul 14 - Wed, Jul 16
BOS
Logan Intl.
PIT
Pittsburgh Intl.
$110 Roundtrip, found 7 hours ago
$110
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Mon, Jul 14 from Logan Intl. to Pittsburgh Intl., returning Wed, Jul 16, priced at $110 found 7 hours ago
Delta
Tue, Aug 26 - Wed, Sep 3
JFK
John F. Kennedy Intl.
PIT
Pittsburgh Intl.
$123 Roundtrip, found 13 hours ago
$123
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Aug 26 from John F. Kennedy Intl. to Pittsburgh Intl., returning Wed, Sep 3, priced at $123 found 13 hours ago