$95 Cheap American Airlines flights Des Moines (DSM) to Chicago (ORD)

Grab affordable return American Airlines flights from $189 from DSM to ORD by organizing your results from "Price (lowest to highest)" on Expedia. Or look for bargains from $95 for a one-way trip.**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.

To find cheap American Airlines fares from Des Moines Intl. Airport (DSM) to O'Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also affect the cost. Sunday tends to be the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your journey on a Sunday.**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 earliest flight from DSM to ORD with American Airlines leaves at 5:30AM UTC-6. You'll land at 7:02AM UTC-6. The final American Airlines flight of the day takes off at 6:00PM UTC-6 and arrives at 7:35PM UTC-6. With approximately 20% fewer cancellations for early and mid-morning flights, jetting out early is often the smartest choice.**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.