Zadar's Dalmatian coastline rewards patience, and after a decade of routing through European hubs to reach it, I've learned that securing business class from Chicago to Zadar almost always means threading the needle through Frankfurt, Munich, or Istanbul rather than hoping for some nonstop miracle that doesn't exist. There is no direct service on this pairing — full stop — so the real decision isn't whether to connect, but which carrier's long-haul product makes the connection worthwhile. Lufthansa's Allegris business class, now rolling out on select 787 and A350 routings from Chicago, offers a genuine step up with its suite-style privacy panels, and Frankfurt's connection to Zagreb Airlines' onward hop or Croatia Airlines' seasonal Zadar service is efficient if you give yourself at least ninety minutes. Turkish Airlines routes through Istanbul, and while the transatlantic leg lacks Lufthansa's newest hard product, the Istanbul lounge remains one of the most lavish in the alliance world, worth the layover on its own merits.
My strong preference is the Munich connection when Lufthansa operates it, simply because Munich's compact Terminal 2 makes tight European turns far less stressful than Frankfurt's sprawl — an insider detail most itinerary planners overlook when pricing this route. Croatia Airlines' Zadar service is seasonal, ramping up heavily from May through September, which means your connecting flight availability from Frankfurt or Munich narrows considerably outside those months, so build buffer time into shoulder-season itineraries. Turkish Airlines, by contrast, tends to run more consistent year-round frequencies into Zagreb or Split with onward domestic hops, a useful fallback if Zadar's own seasonal capacity is thin.
Award and premium cash availability on this Chicago–Zadar corridor fluctuates sharply with Croatia's tourism calendar, and April, May, September, and October consistently offer the best combination of favorable weather and looser business class inventory before or after the peak summer crush. Given how thin and seasonal this routing is, I'd strongly recommend setting up automated fare and award alerts rather than manually checking — the good business class space here disappears fast and reappears without warning.