[Summer Flight Deal] $110: Chicago to Boston (or vice versa)


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Visit Boston for less! Cheap sale on jetBlue nonstop, round-trip flights from Chicago to Boston. This deal also works vice versa if you live in Boston and want to visit the Windy City! Availability in May – September, including all  of the peak summer. jetBlue fare includes seat assignment and free carry-on bag. jetBlue flights offer free wifi during the flight. Book quick, this fare won’t last!


Thrifty Tip #1: Book now and ask questions later! Priceline allows you to cancel any flight within 24 hours of purchase.

Thrifty Tip #2: Check out our article on the best apps for exploring a new city to make a scenic walking route through historic Boston!


Fare Availability:

Chicago to Boston (ORD – BOS) – $110 nonstop/roundtrip

  • Departures: May 22, June 19-20,  July 10-11, 17-18, August 8, 15, 29, September 5, 7-8, 11, 15, 18-22, 25-26, 29, October 2, 16-17
  • Returns: May 30, June 2, 19, July 10-11, 18, 24-25, August 14, 21, September 2, 4-5, 18-19, 26
    • Use return dates as departure dates if flying BOS – CHI

How to Search & Book:

  • We’ve done the searching for you! This flight deal is linked and ready to book on Priceline

Hotel Accommodations:




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