---
title: "Cheap Vacations in South Side 2026 | Expedia.ca"
description: "Find incredible offers on South Side Cheap vacations! Plan your next Cheap trip today with Expedia."
canonical: "https://www.expedia.ca/lp/theme-vacations/cheap-vacations/6343590/South-Side"
language: en-CA
market: CA
currency: CAD
prices_as_of: 2026-11-14T16:21:55Z
---

# South Side Cheap Vacations
![A park with autumn trees, a bridge, and a building labeled UPMC in the background.](https://images.trvl-media.com/place/6343589/4aa9fc8d-6a54-47bc-ab37-20ca38b4643c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

## 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 Cheap vacation packages in South Side

Price found within the past 48 hours. Click for updated prices.

Trip length

3 nights4 nights5 nights6-7 nights

Stars

5 star4 star & up3 star & up2 star & up

Flight class

EconomyPremium economyBusinessFirst class

Remove all filters

- ![An outdoor patio with a fire pit, seating area, and a TV screen.](https://images.trvl-media.com/lodging/5000000/4350000/4342300/4342201/fa81167e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A hotel room with a large bed, a desk with a computer, a TV, and a painting on the wall.](https://images.trvl-media.com/lodging/5000000/4350000/4342300/4342201/b303c99c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 6 - Jan 12**

### [Courtyard by Marriott Pittsburgh Washington/Meadow Lands + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-06/2027-01-12/?FromAirport=YVR&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4342201&dealMarker=&paandie=true&cabinClass=e)
Washington
6 nights

**8.6/10** \- Excellent (1,000 reviews)
Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
YVR - PIT • 1 stop PIT - YVR • 1 stop
[~~CA $1,142~~](https://www.expedia.ca/)

**CA $934**
per traveller
found 1 day ago
- ![A cityscape with high-rise buildings, including a prominent Westin hotel.](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/65ee55fd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 29 - Feb 1**

### [The Westin Pittsburgh, a Marriott Hotel + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-29/2027-02-01/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14295&dealMarker=&paandie=true&cabinClass=e)
Downtown Pittsburgh
3 nights

**8.6/10** \- Excellent (1,001 reviews)
Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
YYZ - PIT • 1 stop PIT - YYZ • 1 stop
[~~CA $1,600~~](https://www.expedia.ca/)

**CA $1,247**
per traveller
found 18 hours ago
- ![A modern bar area with a marble countertop, bar stools, and a bookshelf filled with books and decorative items.](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/52d04c8a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern hotel lobby with a reception desk, a bar area, and a patterned floor.](https://images.trvl-media.com/lodging/29000000/28860000/28852500/28852483/e7c8e126.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 6 - Jan 12**

### [The Oaklander Hotel, Autograph Collection + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-06/2027-01-12/?FromAirport=YVR&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=28852483&dealMarker=&paandie=true&cabinClass=e)
Oakland
6 nights

**9.2/10** \- Wonderful (860 reviews)
"The room was enormous with huge window, so lots of light. The bathroom was spacious and modern. Good quality bath products in large containers so no wasteful mini bottles There was lots of closet and storage space. There was a coffee bar in the room and plenty of bottled water. Room also had a generous sized desk."
Reviewed November 13, 2026
Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
YVR - PIT • 1 stop PIT - YVR • 1 stop
[~~CA $1,570~~](https://www.expedia.ca/)

**CA $1,232**
per traveller
found 1 day ago
- ![A brick building with a large arched entrance labeled "STAYPGH".](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/36fd340f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A modern living room with large windows, a flat-screen TV, a glass table, a sofa, and a lamp.](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/51dffc7e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 29 - Feb 1**

### [Stay Pittsburgh + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-29/2027-02-01/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=77861820&dealMarker=&paandie=true&cabinClass=e)
Downtown Pittsburgh
3 nights

**8.0/10** \- Very good (347 reviews)
Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
YYZ - PIT • 1 stop PIT - YYZ • 1 stop
[~~CA $1,155~~](https://www.expedia.ca/)

**CA $978**
per traveller
found 18 hours ago
- ![A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/5c026a54.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A swimming pool with chairs and a view of a red brick building.](https://images.trvl-media.com/lodging/2000000/1670000/1668500/1668434/cf059c81.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 29 - Feb 1**

### [Hampton Inn & Suites Pittsburgh-Downtown + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-01-29/2027-02-01/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1668434&dealMarker=&paandie=true&cabinClass=e)
Downtown Pittsburgh
3 nights

**9.4/10** \- Exceptional (1,368 reviews)
"The staff, on the whole, were lovely"
Reviewed November 12, 2026
Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
YYZ - PIT • 1 stop PIT - YYZ • 1 stop
[~~CA $1,427~~](https://www.expedia.ca/)

**CA $1,211**
per traveller
found 18 hours ago

## Discover the most popular places to visit in South Side

### Rex Theater

Rating: 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](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests&travelerType=budget%5Fproperty&regionId=553248621533126349)

## Top Cheap South Side Hotels

### [Cozy Loft Studio in a Triplex, near SouthSideWorks](https://www.expedia.ca/Pittsburgh-Hotels-Cozy-Loft-Studio-In-A-Triplex.h131335560.Hotel-Information)

![A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.](https://images.trvl-media.com/lodging/132000000/131340000/131335600/131335560/01aa8418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: Pittsburgh, PA, US
- Location: South Side Flats, 1.6 km from South Side
- Guest rating: 8/10 (Very good, 2 reviews)
- Price: CA $96, CA $218 total, includes taxes & fees, Nov 16 - Nov 17, for Top Cheap South Side Hotels
- Review: Great communication

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.

[See all properties in South Side](https://www.expedia.ca/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&regionId=6343590&adults=2&travelerType=budget%5Fproperty&sort=RECOMMENDED&openPlayBack=true)

## Frequently Asked Questions

### How much does a South Side vacation package cost?

Much less than you might think — from only CA $934, 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](https://www.expedia.ca/Pittsburgh-Hotels-Kasa-Pittsburgh-South-Side.h70891071.Hotel-Information) or [SpringHill Suites by Marriott Pittsburgh Southside Works](https://www.expedia.ca/Pittsburgh-Hotels-SpringHill-Suites-By-Marriott-Pittsburgh-Southside-Works.h3445705.Hotel-Information). 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](https://www.expedia.ca/service/?langid=4105). We're here to help make sure your trip goes off without a hitch.

## Explore a world of travel with Expedia

- [Lodging](?equalTargetTab=tab-0)
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- [Phipps Conservatory](https://www.expedia.ca/Phipps-Conservatory-Central-Oakland.d6078683.Vacation-Attraction)
- [Visit South Side Flats](https://www.expedia.ca/Pittsburgh-South-Side-Flats.dx6343589)
- [Acrisure Stadium](https://www.expedia.ca/Acrisure-Stadium-North-Shore.d6058087.Vacation-Attraction)
- [Cathedral of Learning](https://www.expedia.ca/Cathedral-Of-Learning-Oakland.d6269525.Vacation-Attraction)
- [Visit North Shore](https://www.expedia.ca/Pittsburgh-North-Shore.dx553248633938969308)
- [Visit West Homestead](https://www.expedia.ca/Pittsburgh-West-Homestead.dx6046716)
- [Duquesne Incline](https://www.expedia.ca/Duquesne-Incline-Duquesne-Heights.d6078687.Vacation-Attraction)
- [Children's Museum of Pittsburgh](https://www.expedia.ca/Childrens-Museum-Of-Pittsburgh-North-Side.d6078703.Vacation-Attraction)
- [Schenley Park](https://www.expedia.ca/Schenley-Park-Squirrel-Hill-South.d6078717.Vacation-Attraction)
- [National Aviary](https://www.expedia.ca/National-Aviary-North-Side.d6078697.Vacation-Attraction)
- [Mount Washington Vacations](https://www.expedia.ca/Mount-Washington.d6343586.Destination-Travel-Guides)
- [Visit Strip District](https://www.expedia.ca/Pittsburgh-Strip-District.dx6343592)
- [Enterprise Rental Cars in South Side](https://www.expedia.ca/Enterprise-Car-Rentals-In-South-Side.d6343590-c15.Car-Rental-Guide-Suppliers)
- [Car rentals near Pittsburgh](https://www.expedia.ca/Car-Rentals-In-Pittsburgh.d601717.Car-Rental-Guide)
- [Pittsburgh Vacation Rentals](https://www.expedia.ca/Pittsburgh-Vacation-Rentals.d601717.Travel-Guide-VacationRentals)
- [Things to do in South Side](https://www.expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities)
- [Things to do in Pittsburgh](https://www.expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)

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