Pula's tiny Istrian airport was never built with transatlantic ambitions in mind, which is precisely why the routing puzzle matters more here than almost anywhere else in Croatia. There is no nonstop option, so booking business class from Chicago to Pula means committing to one of three credible connecting strategies: Lufthansa via Frankfurt or Munich, Turkish Airlines via Istanbul, or Croatia Airlines (OU) picking up the final leg from a European gateway. The factual baseline every traveler should know is this: total journey time runs roughly 11.5 hours in the air, but realistic door-to-door timing with a connection typically stretches to 14-16 hours depending on layover length and which hub you choose.
My preference, after flying this corridor several times, leans toward Lufthansa's Allegris business class on the ORD-Frankfurt or ORD-Munich sector when it's available on your date — the redesigned suite with a closing door is a genuine upgrade over the older long-haul cabin, and Frankfurt's connection logistics to Croatia Airlines' regional jets are smoother than they look on paper. Turkish Airlines is the value-conscious alternative, routing through Istanbul with a solid business product and the added bonus of access to their Istanbul lounge, which is worth the layover on its own. Insider tip: fly into Zagreb rather than connecting directly to Pula whenever schedules allow, then take the short Croatia Airlines hop or even a scenic overland transfer in summer — Pula's limited slots mean the final leg often has weaker business availability than the transatlantic segment, so securing that first booking early is critical.
Shoulder seasons — April, May, September, and October — consistently offer the best combination of fare value and manageable Istrian weather, avoiding the July-August coastal crush when every seat on the regional legs gets tight. Given how thin business inventory runs on the connecting flights into Pula, setting up fare and award-space alerts across all three carriers well before you intend to travel will save you from scrambling later.