Flying from Boston to Chicago One Way

Getting from Boston to Chicago is a breeze. "Fly the friendly skies" with United. Other options include major airlines like American, Delta, Southwest, and US Airways as well as smaller carriers like JetBlue, AirTran and Sun Country. It takes as little as 2½ hours to get there, and flights are frequent and affordable. You'll fly out of Logan (BOS) and arrive in either Chicago O'Hare (ORD) or Chicago Midway (MDW).

Flights from Logan (BOS) to Chicago O'Hare (ORD)

Here is a sampling of flights from a Thursday in June, 2014.

First Flight (5:00 am) | Last Flight (9:21 pm) | Shortest Flight (2h 35m)

A few other things to know...

• Flights leave every hour, 7 days a week between 5 am and 9 pm.
• Delta has no direct flights to Chicago.
• Spirit Airlines has one flight per day (2:05 pm-3:45 pm; Nonstop; 2h 40m).
• Manchester (MHT), 44 miles from Boston, has nonstop flights to ORD.
• Check out the latest flight information.

Flights from Logan (BOS) to Chicago Midway (MDW)

Here is a sampling of flights from a Tuesday in July, 2014.

First Flight (5:45 am) | Last Flight (8:20 pm) | Shortest Flight (2h 40m)

A few other things to know...

• Southwest is the only airline to offer direct flights from BOS to MDW.
• Sun Country doesn't have flights on Mondays and Tuesdays.
• All AirTran flights go through Atlanta.
• The airport in Manchester (MHT) has 1-stop flights to MDW.
• Check out the latest flight information.

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