Title: South Side Vacation Packages & Trips 2026 from CA $1,195 | 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.

![Hotel Indigo Pittsburgh East Liberty by IHG](https://images.trvl-media.com/lodging/10000000/9040000/9032700/9032700/112ecec9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

CA $1,195

per person

Feb 27 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8/10 Very Good! (1,003 reviews)

Staff was extremely kind, friendly and helpful! The space was clean and beautiful! The breakfast was delicious!

Reviewed on Jan 11, 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 $1,453

per person

Mar 18 - Mar 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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 $1,442

per person

Feb 27 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

7.6/10 Good! (37 reviews)

Kitchen was fully equipped with everything you would need. The rooms were clean and spacious, beautiful building and friendly staff. Parking is what you would expect in a downtown area but was very easy and the attendant was great.

Reviewed on Jan 14, 2026

![SpringHill Suites by Marriott Pittsburgh Bakery Square](https://images.trvl-media.com/lodging/4000000/3500000/3493400/3493342/603eb9aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SpringHill Suites by Marriott Pittsburgh Bakery Square

Larimer

CA $1,681

per person

Feb 27 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.8/10 Excellent! (1,002 reviews)

Like the location and appreciate the covered parking.

Reviewed on Jan 4, 2026

![Hotel Indigo Pittsburgh University-Oakland by IHG](https://images.trvl-media.com/lodging/20000000/19910000/19901600/19901526/ad7a3ef2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Indigo Pittsburgh University-Oakland by IHG

Oakland

CA $1,480

per person

Feb 27 - Mar 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.6/10 Excellent! (1,002 reviews)

Great room size. Quick check in. Restaurant and bar downstairs.

Reviewed on Jan 11, 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 $99

CA $112 total

Jan 19 - Jan 20

includes taxes & fees

7.2/10 Good! (1,017 reviews)

Yes, the breakfast menu was perfect, and breakfast was fresh.

Reviewed on Jan 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=914423&PinnedHotelID=914423&HadPinnedHotel=true&regionId=6343590)

![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

Fully refundableReserve now, pay when you stay

CA $221

CA $252 total

Jan 24 - Jan 25

includes taxes & fees

9/10 Wonderful! (1,915 reviews)

Hotel was very clean and staff was great

Reviewed on Jan 14, 2026

[](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=2998&PinnedHotelID=2998&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 $153

CA $175 total

Jan 25 - Jan 26

includes taxes & fees

8.2/10 Very Good! (3,344 reviews)

ever

Reviewed on Jan 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true&regionId=6343590)

[See all 1,876 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F01%2F2026&endDate=17%2F01%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

![The Cathedral of Learning! ](https://images.trvl-media.com/place/2800/7e91f442-d07c-4191-854c-601c1dfe33d0.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)

![Heinz Field which includes a lake or waterhole](https://images.trvl-media.com/place/6058087/7963aae8-495d-4502-9a35-a10ea84155c4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Acrisure Stadium

4.5/5(94 reviews)

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

[](https://expedia.ca/Acrisure-Stadium-North-Shore.d6058087.Vacation-Attraction)

### What to do in South Side

![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 $62

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/4572811/58c16208-04c6-4272-8a98-5397d8afb47e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $81

per adult

**94%** of travellers recommend

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

![City Brew Tours](https://mediaim.expedia.com/localexpert/3429134/b701859e-f9ed-4acd-b4a2-62adc3ac258c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Pittsburgh Signature Guided Brewery Tour

CA $144

per adult

[](https://expedia.ca/things-to-do/pittsburgh-signature-guided-brewery-tour.a3429134.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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