Compare cheap flights leaving from Chicago’s major airports — ORD (O'Hare) and MDW (Midway). FlyToDash AI scans both airports instantly to find the lowest fares.
Chicago is one of the world’s busiest and most globally connected aviation hubs, offering travelers two major airport choices: O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare is known for its extensive international connections and premium airline network, while Midway is a strong base for low-cost carriers — especially Southwest — making it an excellent option for budget travelers. With nonstop flights across North America, Europe, the Middle East, Asia, and the Caribbean, Chicago provides some of the most competitive airfare opportunities in the United States.
FlyToDash AI compares flight prices at both ORD and MDW in real time, analyzing fares from legacy airlines, budget carriers, and global international partners. Instead of jumping between airline websites or multiple travel platforms, you get instant, side-by-side comparisons showing the cheapest available flights from both Chicago airports — helping you book smarter and save more.
Chicago travelers enjoy excellent connectivity and strong airline competition, which results in consistently low fares. Some of the most popular and affordable routes from ORD and MDW include:
Airfare from Chicago tends to drop significantly during:
These months offer some of the best opportunities for securing cheap flights from both ORD and MDW.
To maximize savings when flying from Chicago, use these strategies:
FlyToDash AI scans fares from United, American, Delta, Southwest, Spirit, Frontier, JetBlue, Emirates, Turkish Airlines, Qatar Airways, British Airways, and dozens of additional global carriers — all in seconds. Whether you're booking a last-minute business trip, a long-haul international flight, or a family vacation, the AI engine delivers fast, accurate, and transparent results. With real-time price comparison, flexible-date insights, and smart route suggestions, FlyToDash is the easiest and most efficient way to find cheap flights from Chicago’s ORD and MDW airports.