South Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was CA $1,444, price is now CA $1,296 per person
CA $1,296
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,271 reviews)

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,950, price is now CA $1,674 per person
CA $1,674
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
My go to hotel when I’m in Pittsburgh. Easy to get to, parking garage right below the hotel, and great location with a ton of places within walking distance.

Reviewed on Oct 25, 2026

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $1,773, price is now CA $1,526 per person
CA $1,526
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Great location, attentive staff, clean and quiet rooms.

Reviewed on Oct 26, 2026

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
North Side
Price was CA $1,595, price is now CA $1,416 per person
CA $1,416
per person
Dec 9 - Dec 13
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
9.4/10 Exceptional! (2,465 reviews)

Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
Price was CA $1,464, price is now CA $1,314 per person
CA $1,314
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
9/10 Wonderful! (1,793 reviews)
Was a bit confusing getting from extended parking to the hotel entrance. Nice clean quiet room and great food at the restaurant

Reviewed on Oct 28, 2026

Ready to book your vacation to South Side?

 

Choose your dates

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 $110 per night from Nov 30 to Dec 1
CA $110
CA $126 total
Nov 30 - Dec 1
includes taxes & fees
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 $171 per night from Nov 2 to Nov 3
CA $171
CA $195 total
Nov 2 - Nov 3
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Nov 23 to Nov 24
CA $173
CA $197 total
Nov 23 - Nov 24
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
See all 2,025 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

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.
See properties

What to do in South Side

Picture 3 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
86% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

CA $46
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
Best of the Burgh Walking Tour of Pittsburgh

Best of the Burgh Walking Tour of Pittsburgh

CA $46
per adult
100% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
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 $1,296, 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

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