South Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top South Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Pittsburgh - Green Tree
CA $1,308
per person
Dec 18 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,213 reviews)
This place was great! Super clean. Helpful staff! I could drive up to the floor where my room was. Facility was super clean. On-site restaurants were nice. The room was clean. No issues. It was great. I would definitely stay again
Reviewed on Sep 29, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
CA $1,717
per person
Dec 18 - Dec 21
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,659 reviews)
Joinery overall is a great place to stay. In a great location, close to public transit. The HVAC didn’t work in the room.
Reviewed on Sep 29, 2026
Ready to book your vacation to South Side?
South Side Hotel Deals
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
20 S 10th St Pittsburgh PA
Fully refundable
CA $132
CA $150 total
Oct 20 - Oct 21
includes taxes & fees
8/10 Very good! (1,020 reviews)
"Super awesome rooms"
Reviewed on Sep 29, 2026
SpringHill Suites by Marriott Pittsburgh Southside Works
2950 S Water St Pittsburgh PA
CA $186
CA $212 total
Oct 19 - Oct 20
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Lots to do and great places to eat near by. Good breakfast in the morning. Very pleasant staff"
Reviewed on Sep 26, 2026
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $175
CA $200 total
Oct 22 - Oct 23
includes taxes & fees
8.4/10 Very good! (3,811 reviews)
"There's no microwave in the room. Can't warm any food in the room"
Reviewed on Sep 29, 2026
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.
Stay near popular South Side attractions
Rex Theater
6.0/10 (1 review)
You can get tickets for a performance at Rex Theater on your trip to Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.
What to do in South Side
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
86% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
CA $45
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
Frequently asked questions
How much does a South Side vacation package cost?
Much less than you might think — from only CA $1,004, actually! By combining hotels, flights and car rentals into a customized package, your getaway to South Side is just clicks away.
How do I get a cheap travel package to South Side?
Search for flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a South Side vacation package. It's as easy as that! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with more than 550 airlines and 1,000,000 properties around the world to select from, you won't be short of choice.
Where should I stay in South Side?
Travelers come from all over the world to experience Acrisure Stadium and PNC Park in South Side. Book a room near these must-see attractions to make sightseeing a breeze.
What are the top hotels in South Side?
If it's your first visit to South Side, lock in a room at Kasa South Side Pittsburgh or SpringHill Suites by Marriott Pittsburgh Southside Works. Both hotels offer friendly service and are favorites with lots of travelers.
How far in advance should I book my South Side vacation?
Reward yourself with the widest variety at the cheapest prices by booking your South Side vacation early. Airlines generally publish flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to providing you with the best bargains around, so it's never a bad time to book your dream vacation!
What does an Expedia South Side travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply select your favorite bundle and get access to incredible deals. Once you've made your booking, add on a few tours and activities and watch your savings stack up. When it comes to crafting your South Side break, you're in charge!
What should I know before booking a South Side travel package?
You'll score impressive savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together just makes things easier. So why waste your time or money? Whether you're organizing a ritzy romantic getaway or a low-cost family road trip, explore our package deals today.
Can I choose my airline with a South Side Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you want to fly to South Side in business or coach, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my South Side vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel or amend your South Side vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may charge a fee. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
Explore a world of travel with Expedia
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- Flights from Ottawa (YOW) to Pittsburgh (PIT)
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- Roberto Clemente Bridge
- Ppg Paints Arena
- Kennywood
- Visit Strip District
- Market Square
- Mount Washington Vacations
- Pittsburgh Vacations
- Andy Warhol Museum
- Pnc Park
- Sri Venkateswara Temple
- Visit South Side Flats
- Visit Pittsburgh
- The Waterfront
- Visit Downtown Pittsburgh
- Carnegie Museum of Natural History
- Rivers Casino
- National Aviary
- Heinz Hall
- Carnegie Mellon University
- Carnegie Science Center
- Phipps Conservatory
- Visit North Shore
- Duquesne Incline
- Monongahela Incline
- Monroeville Mall
- Schenley Park
- Acrisure Stadium
- Cathedral of Learning
- Children's Museum of Pittsburgh
- Point State Park
- Senator John Heinz Regional History Centre
- Carnegie Museum of Art
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
