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Say I attend UChicago and will be a summer associate in New York. The firm covers my round-trip flights from Chicago to New York. However, if I decide to take a vacation to Europe right afterwards, how does the firm cover my travel expenses? I suppose I could fly back to New York from Europe, and have the firm pay for my flight from New York to Chicago, but what if it's more economical overall if I find a direct and cheaper flight from Europe back to Chicago? Do they reimburse part of this flight?

People have had mixed success with this, make sure to bring it up at the first team meeting this summer.

This happens all the time when working in consulting, etc. Basically I would just submit reimbursement for the cheapest amount it would have taken if I'd gone straight home after, and included a snapshot of both fares (one I requested reimbursement for and actual ticket costs). Never got any push back, most people have more important shit to worry about.

ETA: Actually I did have an open jaw on a job interview once, was flying from overseas and then went home to visit family in another city before returning abroad - I had negotiated a capped reimbursement amount though, which my ticket would have been over regardless.

my firm paid for it

Just ask the travel department as you're booking your flights what they will cover. They aren't going to report your questions to recruiting, and you're just exploring your options under their policy.

FWIW, I was at a wedding in Florida rather my law school city the weekend before my SA started. I bought a one-way ticket to Florida, the firm bought my one-way ticket from Florida to NY, and bought my one-way ticket from NY to law law school city. I just asked if they would do it that way and they said yes, it wasn't a big deal.

firms actually do this? lol jesus