$129 Cheap Delta flights Jackson (JAN) to Chicago (MDW)

You can find cheap return Delta Air Lines flights from $257 from JAN to MDW by organizing your results from "Price (lowest to highest)" on Expedia. Or search for options from $129 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.

Look for cheap Delta Air Lines flights from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW) one to three months before your departure day. 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 class and journey, the best day of the week to book a domestic flight is usually Sunday and the most expensive day 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.

To find the earliest departures from JAN to MDW with Delta Air Lines, filter your search by "Morning" and "Early Morning." Booking an early flight generally means you'll 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.

Offering a rewarding loyalty program and an excellent in-flight experience, Delta Air Lines is a top choice for many travelers heading from JAN to MDW. What's more, if you're a Delta SkyMiles and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles, which can be used on future travel.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.