Italy
in $720s-$930s RT
Ladies aaaaand gentlemen, are you ready to RRUUMMMBBLLLEEEEE?
In the red corner, we have Italy's heavyweight contender and capital city. With a colosseum famous around the world, and one sleeper train away from the Italian Alps, this one really packs a punch.
Or are you backing Venice? Laid-back gondola rides and strolls across Piazza San Marco both offer knockout views. And with its colourful little cousin, Burano, in its corner, the Floating City sure does put up a fight. The cherry on top? These flights will have you touching down during Carnival, when the city transforms into something otherworldly.
With a belly fully of fresh pasta and creamy gelato, we think the real winner is you :-)
DING DING DING
Taking off ✈️
Tip Published: Sep 03, 2026
Round trips to Naples (NAP):
- Montreal (YUL) - $829
- Toronto (YYZ) - $728
- Vancouver (YVR) - $916
Round trips to Rome (FCO):
- Halifax (YHZ) - $939
- Quebec (YQB) - $921
- Saskatoon (YXE) - $930 (2-stop)
- Winnipeg (YWG) - $826 (2-stop)
Round trips to Venice (VCE):
- Ottawa (YOW) - $925 (peak dates)
- Saskatoon (YXE) - $896 (peak dates, 2-stop)
- Winnipeg (YWG) - $821 (peak dates, 2-stop)
How to Book
This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.