Cheap flights from Chicago to Boston
From €105 one way, departing Tue 22 Dec. We compare airlines and travel agencies and add no fees.
Cheapest dates from Chicago to Boston
The lowest one-way fares we found for the coming months. Pick a date to see every flight.
Price history
We have not recorded any prices for ORD to BOS yet. The chart appears after people search this route.
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Plan the rest of your trip to Boston
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Airport transfer in Boston
Arrange a pick-up at Boston airport (BOS) before you fly.
Things to do in Boston
Find tours, tickets and day trips in Boston, United States.
Car rental in Boston
Compare rental cars for Boston (pick up at BOS or in town).
Chicago to Boston: common questions
Answers use the fares we found most recently and are updated through the day.
How much is a flight from Chicago to Boston?
The lowest one-way fare we found recently is €105, departing Tue 22 Dec. A typical cheapest fare on other days is around €137. Prices change often, so check the live price before you book.
Which month is cheapest to fly to Boston?
December 2026 has the lowest fare we found, from €105 on Tue 22 Dec.
How long is the flight from Chicago to Boston?
Chicago and Boston are about 1,390 km apart. A direct flight takes roughly 2.5 hours; flights with a stop take longer.
Does SkimFlight charge a booking fee?
No. SkimFlight compares prices from airlines and travel agencies and sends you to the seller to book. You pay the seller’s price with no fee from us.