Italy 
in $380s-$560s RT
On today's menu: a whole antipasto platter of cheap Italian airfare!
The most famous faces are in attendance, of course (when the Miami-Rome fare drops, it drops hard), but we've also got a few rarer appearances.
Like not one, but two destinations in Sicily, giving us a chance to highlight both the surprisingly bustling city of Palermo and the Old World charm (and active volcano) of Catania.
Or that unusual deal from SF to Turin — the quiet, authentic reprieve at the base of the Alps.
But honestly... it's Italy. There are no wrong choices here :-)
Taking off ✈️
Tip Published: Oct 20, 2025
Round trips from Chicago O'Hare (ORD):
- Catania (CTA) - $547 (checked bag)
- Venice (VCE) - $487
Round trips from Houston (IAH):
- Bologna (BLQ) - $528
Round trips from Miami (MIA):
- Florence (FLR) - $533
- Rome (FCO) - $389
Round trips from Portland (PDX):
- Milan (MXP) - $510
Round trips from San Francisco (SFO):
- Catania (CTA) - $534
- Florence (FLR) - $533
- Palermo (PMO) - $530
- Turin (TRN) - $534
Round trips from Washington Dulles (IAD):
- Naples (NAP) - $568 (checked bag)
- Palermo (PMO) - $531
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.
