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Cheap flights from Chicago

Cheap flights from Chicago start with a choice of two departure airports, and that choice often moves the fare more than the airline does. Travelers from the city head most often to Madrid, Warsaw, Krakow, Chisinau, London, Bucharest, Istanbul, Paris, Milan and Budapest. The carriers serving those routes include Aer Lingus, Air France, Iberia, Icelandair, JetBlue Airways, Lufthansa, Swiss and Skywest Airlines.

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Destinations from Chicago

ToAirlineFlightDatePrice from
WarsawTurkish Airlineswith a stop15 Nov 2026from $571
KrakowLufthansawith a stop16 Oct 2026from $637

Airports — Chicago

Chicago sends you out of two airports. Midway International is the smaller of the pair and sits on the city side, which many travelers prefer for a short trip. O'Hare International is the larger one, and it is the airport to check first when Europe is the plan. The airline you pick decides a lot here: Aer Lingus, Air France, Iberia, Icelandair, Lufthansa and Swiss all fly from the city, alongside JetBlue Airways and Skywest Airlines.

When to go

Departures from Chicago follow the American travel calendar. Summer is the busiest stretch, with school out and families heading for the Madrid, Paris, Milan and London runs, so fares are firmest then. Late autumn and the weeks after the winter holidays are calmer, and midweek departures outside the Thanksgiving and Christmas peaks leave more room to compare. Spring break is another busy window, especially toward Istanbul, Bucharest, Krakow and Warsaw.

Chicago: flights to the city More destinations in USA: flights