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

Scoring cheap one-way Delta Air Lines flights from BOS to ORD from $69 on Expedia is easy — just filter by “Price (lowest to highest).” Or check out our affordable return fares from $137 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.

Delta Air Lines flights to Chicago are often cheaper in the off-peak months of January and February. Whether you need a one-way or round-trip ticket, you could score a better deal then.

Search for affordable Delta Air Lines flights from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) one to three months prior to your 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. No matter the fare class and itinerary, the ideal day 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.

Delta Air Lines has direct flights from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD), with 27 departures each week. Simply choose the “Nonstop” and “Airline” filters while searching on Expedia to see all direct Delta Air Lines flights to ORD.

Leave Logan Intl. Airport (BOS) for O’Hare Intl. Airport (ORD) on a direct Delta Air Lines flight, and you’ll be in the skies for about 3h 2m.

Delta Air Lines has the most flights from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD) on Saturday. With up to 4 daily departures, you’ll get the most choice and flexibility on this day.

Taking off from BOS at 7:15AM UTC-5, the earliest Delta Air Lines flight to ORD lands at 9:21AM UTC-6. Traveling early means you’ll be less likely to experience delays.* Prefer to travel later? The last Delta Air Lines flight from BOS to ORD departs at 8:20PM UTC-5 and touches down at 10:19PM UTC-6.*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.

O’Hare Intl. Airport (ORD) is the main hub for Delta Air Lines flights from Logan Intl. Airport (BOS) to Chicago. But the airline also travels to Midway Intl. Airport (MDW). Be sure to choose Expedia’s “All Airports” option for your destination to see what’s available for your break in Chicago.

Delta Air Lines makes traveling from BOS to ORD more comfortable with a rewarding loyalty program and an excellent in-flight experience. You even have the chance to collect points with Delta SkyMiles. Remember to sign up to Expedia’s free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Delta Air Lines generally uses Embraer 175 planes for journeys from Logan Intl. Airport (BOS) to O’Hare Intl. Airport (ORD). Bear in mind that aircraft type can differ depending on operational requirements, so the plane you board might be different on your day of travel.

Changes are often free within 24 hours of making a booking, but your airline may add a charge after that. For more information about modifying your flights, go to your “Trips,” select your flight and click on “Manage Booking.” If you want the flexibility to adjust your plans without being charged, apply the “No cancel fee” or “Changes included” filter when planning your next adventure.