On his podcast, Clark Howard answers real reader questions on money, credit, debt, retirement, travel, and more, along with co-host Christa DiBiase.

Clark's answer: Since you're in Pittsburgh and she lives in Chicago, the easiest thing is for both of you to meet up in New York. I recommend going a day early so you and your daughter can enjoy some sightseeing together in New York. Start by checking Google Flights to see what’s available. Don't just look at a single airline; look broadly, though keep an eye out for the carriers that put price pressure on that specific market.

Lately, a lot of the best business class discounts to Europe have been on TAP Air Portugal. They’ve been discounting flights around Europe significantly lower than other airlines. While TAP isn't always considered a top-tier business class product, you still get a full lie-flat bed, which makes it a great value option to consider.

Your best bet is to book the cheapest separate round-trip flights you can find for Chicago–New York and Pittsburgh–New York. Spend that extra night together on the way over, but on the way back, you don't necessarily need to overnight in New York since missing a connecting flight home isn't as critical as missing the over-water flight.