Around the Mediterranean
in $400s-$490s RT
Fun fact: Studies show that the Mediterranean diet, a cuisine and culture so iconic it was honored by the UN, is associated with heart health, weight loss, and an overall reduction in early mortality.
Therefore, I think it's totally reasonable to say that flying to southern Europe and spending a week chowing down on moussaka and baklava is the best thing you can do for your health. A Mediterranean vacation might be the only thing standing between you and an early grave!
Luckily, we happened to find a ton of super cheap flights to the south of Europe. We've got the usual favorites like Milan and Athens, but check out the rarer spots too—Tirana and Cyprus are pretty terrific this time of year!
Sure, you could stay healthy by eating vegetables and going to the gym. But this way seems a lot more fun :-)
Taking off ✈️
Tip Published: Oct 14, 2025
Round trips from Boston (BOS):
- Naples (NAP) - $415
- Tirana (TIA) - $407
Round trips from Chicago O'Hare (ORD):
- Nice (NCE) - $494
Round trips from Denver (DEN):
- Athens (ATH) - $492
- Larnaca (LCA) - $497
Round trips from San Diego (SAN):
- Lisbon (LIS) - $449
- Nice (NCE) - $494
- Venice (VCE) - $444
Round trips from San Francisco (SFO):
- Nice (NCE) - $494
Round trips from Seattle (SEA):
- Athens (ATH) - $442
- Larnaca (LCA) - $447
- Lisbon (LIS) - $449
- Milan (LIN) - $447
- Milan (MXP) - $444
- Nice (NCE) - $494
- Venice (VCE) - $444
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.