South Side Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top South Side 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
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Convenient location and while area can be sketchy, people are mostly nice and polite. Hotel perfect for quick trips with nice staff and clean rooms.

Reviewed on Jul. 30, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8/10 Very Good! (2,882 reviews)
Great stay quiet comfortable service was

Reviewed on Jul. 30, 2025

Placemakr Downtown Pittsburgh

Placemakr Downtown Pittsburgh

4 out of 5
Downtown Pittsburgh
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
7.2/10 Good! (10 reviews)
Practical and accessible

Reviewed on Jul. 12, 2025

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (819 reviews)
Affordable, cozy, sleek, clean, would book again actually

Reviewed on Jul. 30, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Location, location, location. The property layout is super convenient with easy access to the convention center and local amenities. Like many properties, I felt the room was not as updated and fresh as the public areas were. Check-in was extremely fast and efficient. The value is in the proximity to the freeway and downtown life.

Reviewed on Jun. 22, 2025

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South Side Hotel Deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

2.5 out of 5
20 S 10th St, Pittsburgh, PA
Fully refundable
The price is CA $145 per night from Aug 3 to Aug 4
CA $145
CA $165 total
Aug 3 - Aug 4
includes taxes & fees
7/10 Good! (1,020 reviews)
"Everything was first class. Very clean and well maintained"

Reviewed on Jul. 27, 2025

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works

3 out of 5
2950 S Water St, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Aug 24 to Aug 25
CA $143
CA $163 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (965 reviews)
"I once again enjoyed my (second) stay. Nice facility in a convenient location with fantastic staff!"

Reviewed on Jul. 26, 2025

SpringHill Suites by Marriott Pittsburgh Southside Works
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
The price is CA $164 per night from Aug 17 to Aug 18
CA $164
CA $187 total
Aug 17 - Aug 18
includes taxes & fees
8/10 Very Good! (2,978 reviews)
"Very convenient location and facing parks. Walking distance to Pirates and Penguins"

Reviewed on Jul. 28, 2025

Wyndham Grand Pittsburgh Downtown
See all 1,788 properties in South Side
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 South Side

PNC Park which includes a city

PNC Park

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

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

University of Pittsburgh
Acrisure Stadium

Acrisure Stadium

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 South Side

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

CA $27
per traveller
Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $185
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
See all activities in South Side

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only CA $1,079, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.