Route Price Intelligence
Cheap Flights From Boston to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
This JetBlue fare from Providence to Chicago usually runs about $389 and just dropped to $225, one of the better discounts we've tracked on this route. Chicago's lakefront, food scene, and architecture tours make it an easy long weekend, and at this price it's a steal for a city with this much going on.
✓ 6 date combinations found at this price
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Best Time to Fly from Boston to Chicago
The cheapest time to fly from Boston to Chicago is typically May, when fares average around $173. The most expensive month tends to be September at around $205. For the best deals, consider flying in May, July, June.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route