$109 Cheap Delta flights Miami (MIA) to Chicago (MDW)

You can find cheap return Delta Air Lines flights from $187 from MIA to MDW by filtering your results from “Price (lowest to highest)” on Expedia. Or search for deals from $109 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.

Search for one-way or round-trip flights to Chicago in January or February. You could find cheaper fares with Delta Air Lines during these off-peak travel months.

Search for affordable Delta Air Lines flights from Miami Intl. Airport (MIA) to Midway Intl. Airport (MDW) one to three months ahead of your day of 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 class and itinerary, the ideal day to book a domestic flight is generally 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 their travel 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 see if there’s a direct journey from MIA to MDW with Delta Air Lines or any other carriers, use our “Nonstop” filter when looking for flights.

To find the earliest departures from MIA to MDW with Delta Air Lines, filter your results by “Early Morning” and “Morning.” Booking an early flight usually means you’re less likely to experience 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.

Delta Air Lines flights from Miami Intl. Airport (MIA) to Chicago arrive at Midway Intl. Airport (MDW). This is the main entry point to this destination.

Heading from MIA to MDW with Delta Air Lines comes with a host of perks, such as a rewarding loyalty program and an excellent in-flight experience. Plus, when you book through Expedia, One Key™ members can earn OneKeyCash™* to redeem on select future travel purchases. That’s on top of the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Depending on the type of ticket you purchased, a fee will generally apply if you cancel or change your flight more than 24 hours after it’s confirmed. To secure plane tickets with more flexibility, select our “Changes included” or “No cancel fee” filter when you look for flights. For more information on modifying or canceling your reservation, head to “Trips,” select your flight and click on “Manage Booking.”