Leave Greenville, SC around 3:00–3:30 PM for Greenville–Spartanburg International Airport (GSP), allowing roughly 25–35 minutes by car depending on traffic and extra time for parking, bag drop, security, and an after-5:00 PM departure. Confirm the exact Air Canada or partner itinerary to Toronto Pearson International Airport (YYZ) and onward to Calgary International Airport (YYC) before leaving; a same-night arrival generally means an 8–10-hour travel day with one connection. At Toronto, follow the signs for connecting passengers and allow enough time for Canadian customs and baggage procedures if your routing requires them.
After landing at Calgary International Airport, collect your bags and take a taxi, rideshare, or prearranged airport shuttle downtown rather than renting a car late at night; the trip to central Calgary is usually 20–30 minutes, traffic permitting. Check in at The Westley Calgary Downtown, Tapestry Collection by Hilton, a convenient base near Stephen Avenue. Expect approximately C$180–350 per night, depending on availability and room type. If you arrive before the kitchen closes, continue to The Beltliner in the Beltline for a relaxed late meal of Canadian comfort food, usually about C$25–45 per person; otherwise, eat at the hotel or nearby, since late-night restaurant options thin out quickly.