$99 Cheap Delta flights Hartford (BDL) to Chicago (MDW)

Scoring cheap one-way Delta Air Lines flights from BDL to MDW from $99 on Expedia is a cinch --- just filter by "Price (lowest to highest)." Alternatively, check out our budget-friendly round-trip fares from $167 for your next exciting vacation.**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 affordable Delta Air Lines flights from Bradley Intl. Airport (BDL) 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 journey, the best day of the week to book a domestic flight is generally Sunday and the most expensive tends to be 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.

Sort your results by "Early Morning" and "Morning" to see the earliest flights from BDL to MDW. Taking off 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.

Flying from BDL to MDW with Delta Air Lines comes with a variety of perks, including an excellent in-flight experience and a rewarding loyalty program. Plus, when booking through Expedia, One Key™ members can earn OneKeyCash™* to use on select future travel purchases. That's in addition to 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.