American Airlines Flights from Boston (BOS) to Chicago (ORD)

One-way flights start as little as and there are roundtrips available from . Get in! You can score some sweet deals with Wotif and American Airlines.

American Airlines flies flights direct every day between Boston (BOS) and Chicago (ORD).

It’s from Boston (BOS) to Chicago (ORD).

At Wotif, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Logan Intl. with: . 

Change of plans? No worries! We’re right here to make things as easy as possible. Check out the American Airlines rules and restrictions in your itinerary. You can also use the No Change Fees filter to find flexible plane tickets for future trips. For more information on how to cancel or change your flight on Wotif, visit our customer service portal.

Just review and compare all our awesome offers or enter your travel dates to see more terrific deals on American Airlines flights from Boston. And remember you can save even more when you bundle a hotel with your flight as part of a Wotif package. Sweet!

We have loads of cheap flights, so just enter your travel dates to see what’s available. If you can be flexible on when you fly, you’ll find even more epic flight deals. So get booking!

The cheapest time of the year for a return trip is . One-way, the cheapest month to fly is . Check our deal cards for details.

It typically takes hours to fly directly from Boston (BOS) to Chicago (ORD).