19 roundtrip flights under $500 from Calgary to someplace warm this fall

Sometimes the fall weather can start to feel a little too chilly, making a sunny getaway feel more tempting than ever. Luckily, Calgary offers roundtrip flights to warm destinations all year round.

These sunny trips are even better when they don’t break the bank, so we’ve rounded up 19 roundtrip flights under $500 to warm destinations to help you escape the cold this fall.

We opted for one-week trips to destinations in October and November 2026.

Liberia

Cost: $482
When: Oct. 29 to Nov. 5, 2026
Airline: WestJet

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San José del Cabo

Cost: $425
When: Oct. 25 to 31, 2026
Airline: WestJet

Puerto Vallarta

Cost: $388
When: Oct. 31 to Nov. 7, 2026
Airline: Flair Airlines

Punta Cana 

Cost: $446
When: Nov. 23 to Dec. 1, 2026
Airline: WestJet

Belize City 

Cost: $499
When: Nov. 20 to 27, 2026
Airline: Air Canada

Manzanillo 

Cost: $402
When: Nov. 26 to Dec. 3, 2026
Airline: WestJet

Mazatlan

Cost: $435
When: Oct. 30 to Nov. 6, 2026
Airline: WestJet

Tulum

Cost: $383
When: Oct. 29 to Nov. 5, 2026
Airline: WestJet

Cancún

Cost: $477
When: Oct. 26 to Nov. 3, 2026
Airline: WestJet

If you feel inclined to visit the United States, here are a few options:

Phoenix

Cost: $321
When: Nov. 26 to Dec. 2, 2026
Airline: WestJet

Miami

Cost: $455
When: Nov. 1 to 10, 2026
Airline: Air Canada

Orlando

Cost: $457
When: Nov. 1 to 8, 2026
Airline: United

Tampa

Cost: $457
When: Nov. 27 to Dec. 5, 2026
Airline: Delta

Houston

Cost: $343
When: Nov. 5 to 11, 2026
Airline: Air Canada

Austin 

Cost: $405
When: Nov. 1 to 9, 2026
Airline: Air Canada

San Diego

Cost: $321
When: Nov. 23 to Dec. 2, 2026
Airline: WestJet

Los Angeles 

Cost: $354
When: Nov. 2 to 8, 2026
Airline: Air Canada

Palm Springs 

Cost: $321
When: Nov. 13 to 19, 2026
Airline: WestJet

Las Vegas

Cost: $290
When: Oct. 25 to Nov. 4, 2026
Airline: WestJet

If you’re curious about the forecast for this September and beyond, we chatted with ECCC about what we could expect this month. As for this winter, the early forecasts are calling for impacts across Alberta from one weather phenomenon.

How to book these flight deals

1. Go to Google Flights
2. Enter Calgary (YYC) in the “Explore” tab
3. Select the departure and return dates that work best for you, along with the lowest fare. We went with week-long trips in October and November.

When seeking airfare deals, be sure to search FlightHub. After finding the most appealing cheap flights, try booking them directly through the specific airline to see if even cheaper deals are available.

Safe travels!