Cheap flights from Chicago from $49

Our data suggests that currently, the cheapest flights from Chicago are being offered by American Airlines, Delta, and JetBlue. For example, American Airlines flights from Chicago to Amman, start at $13, Delta flights from Chicago to Fort Lauderdale cost around $39, and JetBlue flights from Chicago to Amsterdam are around $51.

Currently, the cheapest flight from Chicago found by our users is for $27 to Miami. Prices will vary according to several factors such as the departure date and time, but on average you can expect to pay around $170 to travel from Chicago to Miami.

New York, Los Angeles and Atlanta are currently the destinations served most frequently from Chicago, with 115, 84 and 80 flights per day on average, respectively.

Airlines including American Airlines, Delta and Southwest frequently fly from Chicago. You can view other airlines by performing a quick search in the form above.

If you are looking for a cheap first class flight, consider flights to Tampa, for which the starting price of a first class seat can be as low as $186.

Prices for flights from Chicago are updated daily.

There are 75 operators available for flights from Chicago as of November 2025.

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago.

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.