Southwest Pennsylvania Vacation Packages

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Your Southwest Pennsylvania Vacation

Make the most out of your next break with a tailor-made vacation package to Southwest Pennsylvania. Acquaint yourself with the rich history and all the other things that make this destination an unforgettable experience. With so much to see and do on a trip to Southwest Pennsylvania, it can be hard to know where to start. Kick off your travels in Pittsburgh at Great Allegheny Passage and Kennywood — two popular attractions here. Another great city to add to your itinerary is Washington. Be sure not to miss Hollywood Casino at the Meadows and Tanger Outlet Centre. From the instant you book your Southwest Pennsylvania vacation to when you get back home, Expedia will be with you every step of the way.

Top Southwest Pennsylvania Vacation Deals

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
Price was CA $1,470, price is now CA $1,083 per person
CA $1,083
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.2/10 Very Good! (1,012 reviews)
Staff was very nice!!

Reviewed on Sep 10, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,692, price is now CA $1,249 per person
CA $1,249
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.2/10 Very Good! (2,991 reviews)
Staff was very helpful

Reviewed on Sep 8, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,849, price is now CA $1,410 per person
CA $1,410
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
7.6/10 Good! (20 reviews)
My room was very clean with a beautiful city view. The space is well thought out and very comfortable. There are also a lot of walkable shops and restaurants. Check-in was a little awkward as there was an event in front of the main entrance that I had to walk through with my luggage and speak very loudly over while checking in. Overall it was a nice getaway experience.

Reviewed on Sep 2, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,901, price is now CA $1,457 per person
CA $1,457
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,007 reviews)
It's an excellent hotel in an excellent locale.

Reviewed on Sep 7, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $2,877, price is now CA $2,221 per person
CA $2,221
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Rooms very clean and nice. Every person I encountered was friendly and accomodating. Didn’t like paying $65 for valet parking though.

Reviewed on Aug 30, 2025

Where to stay in Southwest Pennsylvania

Find the best Southwest Pennsylvania areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Pennsylvania
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Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(187 area reviews)

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

Find hotels in Downtown Pittsburgh

Ready to book your vacation to Southwest Pennsylvania?

 

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Southwest Pennsylvania Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Sep 28 to Sep 29
CA $209
CA $239 total
Sep 28 - Sep 29
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
One Bigelow Square, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Sep 28 to Sep 29
CA $174
CA $199 total
Sep 28 - Sep 29
includes taxes & fees
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
The price is CA $220 per night from Sep 29 to Sep 30
CA $220
CA $251 total
Sep 29 - Sep 30
includes taxes & fees
Omni William Penn Hotel
See all 2,794 properties in Southwest Pennsylvania
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Southwest Pennsylvania

PNC Park which includes a city

PNC Park

4.5/5(67 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
University of Pittsburgh

University of Pittsburgh

4.5/5(36 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

University of Pittsburgh
Acrisure Stadium

Acrisure Stadium

4.5/5(94 reviews)

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

Acrisure Stadium

What to do in Southwest Pennsylvania

Immersive American Revolution Self-Guided Walking & Driving Tours

Liberty, Freedom, and Revolution: American History Tours Bundle

CA $41
per traveller
Liberty, Freedom, and Revolution: American History Tours Bundle
Philadelphia: Museum of Illusions Timed Entrance Ticket

Philadelphia: Museum of Illusions Timed Entrance Ticket

CA $35
per adult
98% of travellers recommend
Philadelphia: Museum of Illusions Timed Entrance Ticket
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

Go City: Philadelphia All-Inclusive Pass with 30+ Attractions

CA $81
per adult
80% of travellers recommend
Go City: Philadelphia All-Inclusive Pass with 30+ Attractions
See all activities in Southwest Pennsylvania

Frequently asked questions

Can I cancel my flight booking to Southwest Pennsylvania due to COVID-19?
Our Customer Service Portal has important information about canceling or changing your flight due to COVID-19. Before reserving your tickets, it's a good idea to check the terms and conditions of your preferred airline too.
What's the best way to find cheap flights to Southwest Pennsylvania that have flexible change policies?
We understand that plans can change in a flash, so locking in a flexible airfare with Expedia is a sensible idea. Tick the "No change fee" box under the "Flexible change policies" filter. Your affordable, flexible flight to Southwest Pennsylvania is only a few clicks away.
What are some of the general tips for travelers to Southwest Pennsylvania during the COVID-19 outbreak?
COVID-19 has changed the way we travel, but it hasn't curbed our love of exploring. Here are some tips on how to cope with travel's new challenges:
  • Look into if any restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so don't forget to check before you lock in your flight.
  • When you pass through airport checkpoints, keep your face mask on. You will be asked to lower it briefly to verify your identity. Travelers who refuse to wear a mask may be denied entry or boarding.
  • Instead of handing a TSA officer your boarding pass, position it directly on the reader yourself. After that, hold it up for inspection.
  • You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. You'll need to remove it for X-ray screening.
  • To reduce handling during the screening process, put items such as your phone, wallet and keys into your carry-on rather than into the bins.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Keeping food separate from your carry-on means it's less likely a TSA employee will need to open and touch your bag for inspection.

Which airlines fly to Southwest Pennsylvania?
American Airlines runs flights into or near Southwest Pennsylvania, including 929 that jet into Pittsburgh Intl. Airport (PIT) each month. Select your travel dates and then secure your ticket early for an unbeatable deal.
How can I find cheap tickets to Southwest Pennsylvania?
A good strategy for picking up cheap tickets is to be flexible with your dates. Begin with searching for your flight to Southwest Pennsylvania, then click on the "flexible dates" box to see prices for nearby days. Another handy tip? Book well in advance. To give you an idea of costs, was the best price for a flight to Southwest Pennsylvania in the last seven days.
How much is a flight to Southwest Pennsylvania?
One-way trips departing from () sold for as little as in the last seven days. During this time, the price of a return journey to Southwest Pennsylvania ranged between and . If you spot a bargain ticket, book quickly — these fares don't wait around for long.
What are the most popular airports to fly into in Southwest Pennsylvania?
Pittsburgh Intl. Airport (PIT) is the main entry point for those headed to Southwest Pennsylvania. Roughly 3773 monthly flights land at this airport.
When is the cheapest time to fly to Southwest Pennsylvania?
If you'd prefer to spend your hard-earned vacation money getting to know Southwest Pennsylvania rather than on your trip there, depart earlier in the week. The most affordable day to travel is normally Tuesday, with Monday close behind. With many folks traveling on the weekend, Saturday typically has the most expensive fares.
How much is a plane ticket to Southwest Pennsylvania?
In the last seven days, plane tickets to Southwest Pennsylvania varied between and . Prices tend to go up over time, so grab an awesome deal today.
Which airlines with flights to Southwest Pennsylvania employ COVID-19 cleanliness policies?
Physical distancing is just one element of new travel measures to reduce the spread of COVID-19. From the moment you check in, these airlines will bring you to Southwest Pennsylvania with greater peace of mind:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.