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Flights from Boston to Chicago (BOS to ORD and MDW)

Boston to Chicago is a busy Northeast-to-Midwest route with frequent nonstop service. Flights from Logan International (BOS) reach Chicago in about 2.5–3 hours, with departures throughout the day on multiple carriers.

Chicago O'Hare (ORD)

Most flights from Boston land at O'Hare, the larger of Chicago's two airports. United, American, Delta, JetBlue, and Spirit all operate nonstop BOS–ORD service. O'Hare is connected to downtown Chicago via the CTA Blue Line train (about 45 minutes, $5).

Chicago Midway (MDW)

Southwest Airlines dominates Midway with frequent nonstop flights from Boston. Midway is closer to downtown and connected via the CTA Orange Line (about 25 minutes, $5). Fares on Southwest to Midway are often competitive, especially when you factor in Southwest's free checked bags and no change fees.

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