Boston to Chicago $90 Round-Trip, Nonstop, on Southwest

Here's a great round-trip domestic fare for under $100. Searching Southwest, we found seats from Boston to Chicago for $90 nonstop.

Depart BOS on Wednesday, October 25, returning from MDW on Tuesday, October 31.

Other dates are also available for travel through December 13.

See our fare details for booking info.

Need a room in Chicago? Here's what's available for the above dates on Hotelwatchdog.

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