Chicago gives you two strong options: ORD for the biggest airline selection (especially international), and MDW for quick domestic value. Prices can swing a lot by day-of-week and season— FlyToDash AI scans both airports so you don’t miss the cheaper option.
Chicago is one of the best U.S. cities for flight deals because it has two major airports competing for travelers. O’Hare (ORD) usually has the widest selection—especially for international routes and major connections—while Midway (MDW) can be the better play for domestic trips when you want simple, quick options.
Winter weather can affect schedules. If you’re traveling in peak winter weeks, avoid tight connections and consider slightly earlier departures. Sometimes paying a little more for a better timing reduces risk.
Use the search tool above to compare flights from both ORD and MDW. If the price looks high, the nearby airports section below keeps things local and helps you cross-check alternatives without a giant “template” grid.