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  1. Use Google Flights to explore cheap flights to anywhere. Search destinations and track prices to find and book your next flight.

  2. Compare Southwest Airlines flights to Chicago Midway now. Find flight deals, the easiest route or the cheapest time to fly, all with no added fees.

  3. Search and book cheap flights from New York to Chicago on Booking.com! Compare routes, airlines, and prices to find the right flight for your trip.

  4. Compare Southwest Airlines flights to New York LaGuardia now. Find flight deals, the easiest route or the cheapest time to fly, all with no added fees.

  5. Our data shows that the cheapest route for a one-way flight from New York to Chicago cost $54 and was between New York LaGuardia Airport and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from New York LaGuardia Airport to Chicago Midway Airport.

  6. Find flights to Chicago Midway Airport from $50. Fly from New York on Frontier, Southwest, Delta and more. Search for Chicago Midway Airport flights on KAYAK now to find the best deal.

  7. Budget airlines, including Southwest, offer nonstop flights from MDW to NYC. Consider booking your flight from Chicago to La Guardia Airport (LGA) if you’re headed to Manhattan. LGA is the airport closest to downtown New York City, and taxis and public buses are available at the airport.