Cheap flights from Boston to Chicago
Fares from $119 in November 2026. Compare every month below, then book with the site you like.
Search Boston → Chicago flightsCheapest Boston to Chicago fares by month
Lowest price per person found in recent searches. Prices change often and are checked when you book.
- November 2026Nov 14 · one way · Frontier · 1 stop$119See deal
- December 2026Dec 22 · one way · Southwest · Direct$150See deal
- January 2027Jan 4 · one way · Southwest · Direct$149See deal
- March 2027Mar 16 · one way · JetBlue · Direct$178See deal
- July 2027Jul 23 · one way · American Airlines · Direct$179See deal
Boston to Chicago at a glance
- Distance864 miles
- Nonstop flight timeabout 2h 30m
- Cheapest monthNovember 2026
- Airport codesBOS → CHI
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Frequently asked questions
- How much is a flight from Boston to Chicago?
- The cheapest fare we found recently is $119 per person, departing Nov 14 on Frontier. Prices change daily, so search your dates to see today's fares.
- What is the cheapest month to fly from Boston to Chicago?
- November 2026 is currently the cheapest month, from $119. July 2027 is the most expensive, from $179.
- Are there direct flights from Boston to Chicago?
- Yes. Recent searches found nonstop fares from $149.
- Which airlines fly from Boston to Chicago?
- The cheapest recent fares on this route were on Frontier, Southwest, JetBlue, American Airlines.
- How long is the flight from Boston to Chicago?
- Boston and Chicago are about 864 miles apart, so a nonstop flight takes roughly 2h 30m. Flights with a stop take longer, depending on the connection.
- How do I find the cheapest flight from Boston to Chicago?
- Search your dates on Gotoesy. We list fares from several booking sites sorted cheapest first, show nearby dates when your day has no saved fare, and send you straight to the seller to book.
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