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Cheap flights from Chicago to Boston

Fares from $110 in November 2026. Compare every month below, then book with the site you like.

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Cheapest Chicago to Boston fares by month

Lowest price per person found in recent searches. Prices change often and are checked when you book.

Chicago to Boston at a glance

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Frequently asked questions

How much is a flight from Chicago to Boston?
The cheapest fare we found recently is $110 per person, departing Nov 21 on Frontier. Prices change daily, so search your dates to see today's fares.
What is the cheapest month to fly from Chicago to Boston?
November 2026 is currently the cheapest month, from $110. March 2027 is the most expensive, from $189.
Are there direct flights from Chicago to Boston?
Yes. Recent searches found nonstop fares from $179.
Which airlines fly from Chicago to Boston?
The cheapest recent fares on this route were on Frontier, American Airlines.
How long is the flight from Chicago to Boston?
Chicago and Boston 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 Chicago to Boston?
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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