$99 Cheap Delta flights Tampa (TPA) to Chicago (MDW)

You can find cheap round-trip Delta Air Lines flights from $190 from TPA to MDW by sorting your results from “Price (lowest to highest)” on Expedia. Or search for options from $99 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.

January is one of the least expensive months to fly to Chicago with Delta Air Lines. You could also find excellent prices on one-way and return fares in February.

Begin your search one to three months before your departure to score cheaper fares on Delta Air Lines flights from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also cut costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Get the timing right, and you can enjoy significant savings on domestic journeys.*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.

Enter your dates, click search and select “Nonstop” on Expedia to browse any direct flights from TPA to MDW with Delta Air Lines or another carrier.

Filter your results by “Early Morning” and “Morning” to see the earliest departures from TPA to MDW. Leaving early means flight cancellations are less likely.**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.

Jump on a Delta Air Lines flight from Tampa Intl. Airport (TPA) to Chicago, and you’ll probably touch down at Midway Intl. Airport (MDW). This is the airline’s primary hub in this destination.

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

Changes are often free within 24 hours of making a booking, but your airline may add a charge after that. For more details about modifying your flights, go to your “Trips,” select your flight and click on “Manage Booking.” If you’d like the freedom to adjust your plans without additional costs, tick the “No cancel fee” or “Changes included” filter when planning your next break.