IB vs. AY Y
 

I am traveling from VIE to JFK in April on an award ticket. I have a choice of IB Y via MAD or AY Y via HEL. Each route has a 22/23 layover in the connecting city. Any thoughts on which route will give me the best experience?

(I am flying to VIE in OS J, but only have enough miles for J one way.)

Personally I would keep looking until I had a flight with a 1.5-2 hour connection...

But if you want to see something during those 22-23 hours go to Madrid, the airport is less remote with better ground transport/cheaper taxis.

While I enjoyed my last visit to HEL, I wouldn't recommend a quick visit in April.

Soon (June/July?) AB/HG will be in oneworld and connections will get easier (at least from VIE).

Madrid for the city......AY for the airline!

Depends on what you are looking for in a city. HEL would be my choice for the stopover. The downtown bus transport is efficient and reasonable value. Your timing might allow a return ferry excursion to Tallinn so you can see how the Finns do the "booze cruise" to acquire as much alcohol as possible at Estonian prices (typically half that charged in Finland).

+1, fully agree, the trip to Tallinn is really worthwhile. You can get the jetfoil from Helsinki central to Tallinn in about an hour, and both cities fully deserve the look around. Get the tram around the old town in Tallinn. Plus AY Lounge in HEL is worth the visit, especially for the spa.