[American] $110: Chicago to Boston (Nonstop / Roundtrip)

This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For more information check out our Advertising Disclosure.


See Boston for less! Great sale on American Airlines nonstop, round-trip flights from Chicago to Boston. Availability May – June & August – November. This flight deal also works vice versa, if you live in Boston and want to visit Chicago. All round-trip flights include free carry-on. Advance seat assignment is extra. Book quick, this fare won’t last!

This fare is American’s “Basic Economy fare” which does not allow seat assignment until check-in. This fare still allows free carry-on bags.

Thrifty Tip #1: Book now and ask questions later! You can cancel up to 24 hours after booking with Priceline.

Thrifty Tip #2: Read about How to Spend the Perfect Weekend in Boston.


Fare Availability:

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

  • Departures: May 14, 21, August 28, September 4-5, 7, 9-11, 16-18, 21, 24-25, 28, October 1-2, 8-9, 12, 16, 22-23, 26, 29-30, November 2, 5-6, 9, 12-13
  • Returns: May 14, 16, June 4, 12, 19, August 7, 14, 21-22, 27-29, September 3-5, 7, 10-12, 14, 17-19, 21, 24-26, October 1-3, 8-9, 15-16, 22-23, 29-31, November 5-6, 9, 12-13
    • Some dates work vice versa, will take trial and error.

How to Search & Book:

  • Book via Priceline we’ve done the searching for you!
    • Learn how to get free TSA PreCheck & save $500 off your next flight with the Capital One Venture card.

Hotel Accommodations:




Subscribe to our Newsletter, like us on Facebook, and follow us on Twitter & Instagram


Editorial Note: Any opinions, analyses, reviews, or recommendations expressed in this article are those of the author’s alone, and have not been reviewed, approved, or otherwise endorsed by any card issuer.

Leave a Reply

Your email address will not be published. Required fields are marked *