$190 Cheap American Airlines flights Chicago (ORD) to Madison (MSN)

Use the "Price (lowest to highest)" filter on Expedia to search for cheap American Airlines return flights from $179 from ORD to MSN. Affordable one-way tickets from $190 are available too.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Search for cheap American Airlines flights from O'Hare Intl. Airport (ORD) to Dane County Regional Airport (MSN) one to three months ahead of your departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare type and itinerary, the best day of the week to book a domestic flight is generally Sunday and the most expensive is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

The first American Airlines flight from ORD to MSN departs at 10:11AM UTC-6, landing at 11:13AM UTC-6. If you prefer to set off later in the day, the last American Airlines flight leaves ORD at 8:40PM UTC-6 and touches down at MSN at 9:50PM UTC-6. Flying before midday is often a smart choice as morning and mid-morning flights tend to experience fewer cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.