$153 Cheap Delta flights Boston (BOS) to Chicago (MDW)

Set the “Price (lowest to highest)” filter on Expedia to find cheap Delta Air Lines return flights from $137 from BOS to MDW. Affordable one-way options from $153 are also on offer.**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 most affordable months to jet off to Chicago with Delta Air Lines. You could also find great deals on one-way and round-trip tickets in February.

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

Click on our “Nonstop” filter when looking for direct Delta Air Lines flights from BOS to MDW. You can also compare other airlines offering the same nonstop journey.

Browse Delta Air Lines’s earliest flights from BOS to MDW by checking the “Morning” and “Early Morning” filters. Not only will you arrive sooner, early departures are also 20% less likely to be canceled.**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 Logan Intl. Airport (BOS) to Chicago arrive at Midway Intl. Airport (MDW). This is the main entry point to this city.

Delta Air Lines makes traveling from BOS to MDW enjoyable with an excellent in-flight experience and a rewarding loyalty program. You could even start earning points with Delta SkyMiles. Be sure to sign up to Expedia’s free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future travel.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Changes are typically free within 24 hours of making a booking, but your airline may add a charge after that time. For more information about modifying your reservation, go to your “Trips,” select your flight and click on “Manage Booking.” If you want the flexibility to make changes without extra charges, check the “No cancel fee” or “Changes included” filter when organizing your next adventure.