The Chicago-to-Munich corridor is one of those routes that rewards loyalty to a single alliance, because both United and Lufthansa operate it under the Star Alliance umbrella — and knowing which metal to choose on a given travel window can make an enormous difference in how you arrive. Lufthansa's nonstop from O'Hare remains the gold standard here, with their Business Class cabin offering the Allegris seat on newer A350 configurations — a genuine lie-flat revolution with direct aisle access from every position — while United's Polaris product on the same route holds its own admirably, particularly on 787-9 deployments where the reverse herringbone layout delivers genuine privacy for a nine-hour crossing.
O'Hare's Terminal 5 is where this journey truly begins, and seasoned travelers know to arrive with intention rather than urgency. The international terminal's United Club and Lufthansa's access arrangements through partner lounges are worth factoring into your departure strategy, though neither approaches the quality you'll find waiting for you at Munich's Terminal 2 — a Lufthansa-operated masterpiece of efficiency where the Senator Lounge consistently outperforms nearly every other European hub lounge in terms of food quality and calm atmosphere.
Seasonally, this route behaves in a particularly interesting way. The Bavarian shoulder seasons — October and early November especially, just as Oktoberfest crowds dissolve and before ski season inflates demand — consistently surface the most compelling award availability and negotiated fare windows. January through March offers similar softness on the demand side, making those months ideal for positioning a business trip or a long-weekend escape to Munich before the rest of the world remembers how exceptional the city is in winter.