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Note about this deal
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Of late, cheap fares to Europe have been getting tough to dig up, so these low fares to Milan and Venice in fall shoulder season (for our money, the best time to visit Italia, and we live there), are a sight for sore eyes.
If you want to tick a second destination off your list, trip slipping off the layover filters in Google Flights, like this. In some cases, you can work an almost-full-day stopover in Madrid into your itinerary for the same price.
Note that if you want a checked bag here, it's much cheaper to upgrade to 'Economy Standard' while booking ($60 each way) than it is to buy the cheapest fare and add a bag after.
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Airlines and baggage
