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Cheap flights to Chicago

Cheap flights to Chicago bring you to a lakefront city with a deep food and live-music scene. People fly in for business downtown, for university visits and for long summer weekends by the water. The busiest stretch runs from late spring into early autumn, and again over the winter holidays, when airfare tends to rise.

Search opens on kissandfly.com — that's where you buy the ticket.

Flights to Chicago — where from

FromAirlineFlightDatePrice from
KrakowScandinavian Airlineswith a stop15 Dec 2026from $487
WarsawLOT Polish Airlinesdirect17 Nov 2026from $683
RzeszowLOT Polish Airlineswith a stop18 Sept 2026from $1,006

Airports — Chicago

Flights to Chicago land at either Midway International or O'Hare International. O'Hare is the larger field, further from the centre, with trains, buses, shuttles and rideshares running in through the day. Midway sits closer to downtown, so the train, taxi or rideshare leg is short. Carriers on these routes include American Airlines, British Airways, Iberia, Aer Lingus, Icelandair, Scandinavian Airlines, Cityjet and Portug. Check which airport your fare uses before booking, because the two are far apart.

When to go

Summer brings warm days, lake breezes and a busy festival season that keeps planes full. Spring and autumn are milder and calmer, often the easier time to find a seat. Winter is cold and windy, with snow that can slow travel, though the city rarely stops. Midweek business travel fills cabins, so weekends can be quieter.

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