$69 Cheap Delta flights Chicago (MDW) to Boston (BOS)

Apply the "Price (lowest to highest)" filter on Expedia to search for cheap Delta Air Lines round-trip flights from $110 from MDW to BOS. Affordable one-way fares from $69 are available too.**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.

For cheap Delta Air Lines fares from Midway Intl. Airport (MDW) to Logan Intl. Airport (BOS), start searching one to three months before your planned 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 impact the overall cost. Sunday is usually the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking 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.

Sort your results by "Morning" and "Early Morning" to see the earliest departures from MDW to BOS. Heading 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.

Jetting off from MDW to BOS with Delta Air Lines means enjoying a host of perks, including a rewarding loyalty program and an excellent in-flight experience. Plus, when booking 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.