Spain, Italy & Portugal 
in $280s-$440s RT
Oh, these? These are just some TAP fares we found.
Yeah, no big deal. Just the cheapest prices we've ever seen for super cool cities like Venice and Madrid. Mhmm, Rome too. Most of them are lower than ever before, now that you mention it. And the rest are the cheapest we've spotted in years.
But honestly, we're mainly excited about our first ever deal from the US to Porto Santo. Read on for an introduction to the Golden Island, courtesy of Flight Finder Andreia—our expert on all things Portuguese :-)
Taking off ✈️
Tip Published: Jul 07, 2025
Round trips from Boston (BOS):
- Madrid (MAD) - $294
- Milan (MXP) - $325
- Rome (FCO) - $307
Round trips from Chicago (ORD):
- Barcelona (BCN) - $328
- Madrid (MAD) - $295
- Rome (FCO) - $310
Round trips from Los Angeles (LAX):
- Madrid (MAD) - $308
- Milan (MXP) - $335
Round trips from Miami (MIA):
- Madrid (MAD) - $294
- Rome (FCO) - $312
- Tenerife (TFS) - $445
Round trips from New York (EWR):
- Alicante (ALC) - $318
- Bilbao (BIO) - $318
- Bologna (BLQ) - $315
- Florence (FLR) - $314
- Ibiza (IBZ) - $318
- Madrid (MAD) - $292
- Milan (MXP) - $294
- Minorca (MAH) - $308
- Málaga (AGP) - $316
- Naples (NAP) - $292
- Palma De Mallorca (PMI) - $342
- Porto Santo (PXO) - $423
- Seville (SVQ) - $310
- Tenerife (TFS) - $371
- Valencia (VLC) - $317
- Venice (VCE) - $314
Round trips from New York (JFK):
- Alicante (ALC) - $309
- Bilbao (BIO) - $308
- Bologna (BLQ) - $315
- Florence (FLR) - $314
- Ibiza (IBZ) - $318
- Madrid (MAD) - $294
- Milan (MXP) - $287
- Minorca (MAH) - $342
- Málaga (AGP) - $316
- Naples (NAP) - $315
- Seville (SVQ) - $317
- Tenerife (TFS) - $371
- Valencia (VLC) - $316
- Venice (VCE) - $314
Round trips from San Francisco (SFO):
- Madrid (MAD) - $296
- Milan (MXP) - $385
Round trips from Washington DC (IAD):
- Madrid (MAD) - $294
- Milan (MXP) - $340
- Rome (FCO) - $365
How to Book
This is a Premium deal for Jack's Flight Club members only. For step by step instructions on how to book it you'll need to login or upgrade to Premium membership.
