Title: South Side Vacation Packages & Trips 2026 from CA $869 | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx6343590)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d6343590.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d6343590.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d6343590.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d6343590.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6343589/4aa9fc8d-6a54-47bc-ab37-20ca38b4643c.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# 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 $1,096 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.

![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

CA $869

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Pittsburgh (PIT)

8.2/10 Very Good! (3,142 reviews)

Staff were outstanding, and very helpful. Pool and hot tub was nice to have, especially the hot tub. Food in the hotel restaurant was OK, but nothing spectacular.

Reviewed on Feb 6, 2026

![Stay Pittsburgh](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/7b586e0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Stay Pittsburgh

Downtown Pittsburgh

CA $1,563

per person

Apr 24 - Apr 26

found 9 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Pittsburgh (PIT)

7.8/10 Good! (203 reviews)

Clean and very cozy

Reviewed on Feb 1, 2026

![The Westin Pittsburgh, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

CA $1,293

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Pittsburgh (PIT)

8.6/10 Excellent! (1,003 reviews)

Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

CA $1,773

per person

Apr 24 - Apr 26

found 9 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Pittsburgh (PIT)

7.6/10 Good! (37 reviews)

Very friendly staff and clean room.

Reviewed on Feb 1, 2026

![DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/4d6098b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh

CA $1,800

per person

Apr 24 - Apr 26

found 9 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Pittsburgh (PIT)

8.2/10 Very Good! (1,011 reviews)

Daytime staff was awesome! They came to our rescue with bedsheets and pillows for the pullout couch.

Reviewed on Feb 4, 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](https://images.trvl-media.com/lodging/1000000/920000/914500/914423/76c1ea4b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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

20 S 10th St Pittsburgh PA

Fully refundable

CA $97

CA $111 total

Feb 18 - Feb 19

includes taxes & fees

7.2/10 Good! (1,001 reviews)

Friendly staff. Clean , comfortable rooms

Reviewed on Jan 28, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&selected=914423&PinnedHotelID=914423&HadPinnedHotel=true&regionId=6343590)

![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $164

CA $187 total

Feb 11 - Feb 12

includes taxes & fees

8.2/10 Very Good! (3,396 reviews)

Beautiful hotel. So close to downtown. Loved it.

Reviewed on Feb 2, 2026

[](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true&regionId=6343590)

![La Quinta Inn by Wyndham Pittsburgh Airport](https://images.trvl-media.com/lodging/1000000/10000/2500/2472/b3836cb9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

La Quinta Inn by Wyndham Pittsburgh Airport

8507 University Blvd Coraopolis PA

Fully refundableReserve now, pay when you stay

CA $84

CA $96 total

Feb 22 - Feb 23

includes taxes & fees

8/10 Very Good! (2,227 reviews)

All was great

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=2472&PinnedHotelID=2472&HadPinnedHotel=true&regionId=6343590)

[See all 1,937 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&regionId=6343590)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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

![University of Pittsburgh in Pittsburgh, PA ](https://images.trvl-media.com/place/6090505/783a779d-9b7b-411b-8978-ebc0679a7952.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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 acclaimed theater scene in this vibrant area. 

[](https://expedia.ca/University-Of-Pittsburgh-Oakland.d6090505.Vacation-Attraction)

![PNC Park which includes a city](https://images.trvl-media.com/place/6034814/2a1c2913-9c06-4fae-9abc-1cb74729e1af.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](https://expedia.ca/PNC-Park-North-Shore.d6034814.Vacation-Attraction)

![Mario Lemieux statue](https://images.trvl-media.com/place/2800/a1d63919-12b6-4170-9f84-3ebbdf3ed244.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### PPG Paints Arena

5/5(80 reviews)

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area. 

[](https://expedia.ca/PPG-Paints-Arena-Downtown-Pittsburgh.d6140367.Vacation-Attraction)

### What to do in South Side

![Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://mediaim.expedia.com/localexpert/697587/fb378b65-03b5-422b-84c6-ec829fe06b75.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18

per adult

[](https://expedia.ca/things-to-do/pittsburgh-bar-hunt-party-through-pittsburgh-bar-crawl.a697587.activity-details)

![Make new friends as you learn the exciting history of whiskey in Pittsburgh](https://mediaim.expedia.com/localexpert/1359320/44c64494-c602-43ff-a552-b170c4986e13.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Whiskey Rebellion & Prohibition Tour

CA $68

per adult

[](https://expedia.ca/things-to-do/whiskey-rebellion-prohibition-tour.a1359320.activity-details)

![Pittsburgh: Beauty of the Burgh Bike Tour](https://mediaim.expedia.com/localexpert/4572811/f96e6be9-59d9-405e-9cf4-20718d608bf0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Pittsburgh: Beauty of the Burgh Bike Tour

CA $82

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/pittsburgh-beauty-of-the-burgh-bike-tour.a4572811.activity-details)

[See all activities in South Side](https://expedia.ca/things-to-do/search?rid=6343590)

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- [Andy Warhol Museum ](https://www.expedia.ca/Andy-Warhol-Museum-North-Shore.d6078695.Vacation-Attraction)
- [Carnegie Mellon University ](https://www.expedia.ca/Carnegie-Mellon-University-Squirrel-Hill.d6090503.Vacation-Attraction)
- [Carnegie Museum and Library ](https://www.expedia.ca/Carnegie-Museum-And-Library-Pittsburgh.d6215067.Vacation-Attraction)
- [Carnegie Museum of Art ](https://www.expedia.ca/Carnegie-Museum-Of-Art-Oakland.d6078685.Vacation-Attraction)
- [Carnegie Museum of Natural History ](https://www.expedia.ca/Carnegie-Museum-Of-Natural-History-Oakland.d6078701.Vacation-Attraction)
- [Carnegie Science Center ](https://www.expedia.ca/Carnegie-Science-Center-North-Side.d6078691.Vacation-Attraction)
- [Cathedral of Learning ](https://www.expedia.ca/Cathedral-Of-Learning-Oakland.d6269525.Vacation-Attraction)
- [Children's Museum of Pittsburgh ](https://www.expedia.ca/Childrens-Museum-Of-Pittsburgh-North-Side.d6078703.Vacation-Attraction)
- [Duquesne Incline ](https://www.expedia.ca/Duquesne-Incline-Duquesne-Heights.d6078687.Vacation-Attraction)
- [Heinz Hall ](https://www.expedia.ca/Heinz-Hall-Downtown-Pittsburgh.d6163670.Vacation-Attraction)
- [Kennywood ](https://www.expedia.ca/Kennywood-Pittsburgh.d6193719.Vacation-Attraction)
- [Manor Theatre ](https://www.expedia.ca/Manor-Theatre-Squirrel-Hill-South.d553248621532660405.Vacation-Attraction)
- [Market Square ](https://www.expedia.ca/Market-Square-Downtown-Pittsburgh.d553248621532660539.Vacation-Attraction)
- [Monongahela Incline ](https://www.expedia.ca/Monongahela-Incline-South-Shore.d6078693.Vacation-Attraction)
- [Mount Washington Vacations ](https://www.expedia.ca/Mount-Washington.d6343586.Destination-Travel-Guides)
- [National Aviary ](https://www.expedia.ca/National-Aviary-North-Side.d6078697.Vacation-Attraction)
- [North Side Vacations ](https://www.expedia.ca/North-Side.d6346454.Destination-Travel-Guides)
- [Pnc Park ](https://www.expedia.ca/PNC-Park-North-Shore.d6034814.Vacation-Attraction)
- [Ppg Paints Arena ](https://www.expedia.ca/PPG-Paints-Arena-Downtown-Pittsburgh.d6140367.Vacation-Attraction)
- [Phipps Conservatory ](https://www.expedia.ca/Phipps-Conservatory-Central-Oakland.d6078683.Vacation-Attraction)
- [Visit Bluff ](https://www.expedia.ca/Pittsburgh-Bluff.dx553248634333003951)
- [Visit Downtown Pittsburgh ](https://www.expedia.ca/Pittsburgh-Downtown-Pittsburgh.dx6057662)
- [Visit South Side Flats ](https://www.expedia.ca/Pittsburgh-South-Side-Flats.dx6343589)
- [Visit Terrace Village ](https://www.expedia.ca/Pittsburgh-Terrace-Village.dx804080730279682048)
- [Pittsburgh Vacations ](https://www.expedia.ca/Pittsburgh.d601717.Destination-Travel-Guides)
- [Visit Pittsburgh ](https://www.expedia.ca/Pittsburgh.dx601717)
- [Point State Park ](https://www.expedia.ca/Point-State-Park-Downtown-Pittsburgh.d6078711.Vacation-Attraction)
- [Roberto Clemente Bridge ](https://www.expedia.ca/Roberto-Clemente-Bridge-Pittsburgh.d6078721.Vacation-Attraction)
- [Schenley Park ](https://www.expedia.ca/Schenley-Park-Squirrel-Hill-South.d6078717.Vacation-Attraction)
- [Senator John Heinz Regional History Centre ](https://www.expedia.ca/Senator-John-Heinz-Regional-History-Centre-Downtown-Pittsburgh.d6078699.Vacation-Attraction)
- [Southwest Pennsylvania Vacations ](https://www.expedia.ca/Southwest-Pennsylvania.d6057625.Destination-Travel-Guides)
- [The Waterfront ](https://www.expedia.ca/The-Waterfront-Pittsburgh.d553248621532660523.Vacation-Attraction)
- [Upmc Shadyside ](https://www.expedia.ca/UPMC-Shadyside-Shadyside.d6269693.Vacation-Attraction)
- [University of Pittsburgh ](https://www.expedia.ca/University-Of-Pittsburgh-Oakland.d6090505.Vacation-Attraction)

- [Things to do in Pittsburgh ](https://www.expedia.ca/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)

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