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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
DublinIcelandairwith a stop8 Jan 2027from $431
LondonIcelandairwith a stop9 Feb 2027from $573
RzeszowLOT Polish Airlineswith a stop24 Dec 2026from $759
KrakowLOT Polish Airlineswith a stop23 Nov 2026from $857
WarsawLOT Polish Airlineswith a stop13 Nov 2026from $892

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