Cheap flights from Boston to Chicago
Flights from Boston to Chicago currently start at €79. Below are the cheapest dates, typical duration and airlines on this route. Search live fares when you are ready to book — prices change during the day.
Prices refresh daily · per adult · Typical time: 3h 1m
Key facts
- Lowest fare
- €79 · Wed 4 Nov
- Direct flights
- Yes
- Flight time
- 3h 1m
- Airlines
- jetBlue, Southwest Airlines, American Airlines, Frontier Airlines
- Cheapest month
- November 2026
- Distance
- 1369 km
Round trip
One way
Questions people ask before they book
How much are flights from Boston to Chicago?
The lowest fare we currently show from Boston to Chicago is €79 for one adult. That price is tied to specific dates and can sell out.
Are there direct flights from Boston to Chicago?
Yes. Direct flights from Boston to Chicago show up in current fares. Filter by Direct when you search to hide connections.
Which airlines fly from Boston to Chicago?
Airlines showing fares on this route include jetBlue, Southwest Airlines, American Airlines, Frontier Airlines, United Airlines. The cheapest airline is not always the one with a bag included.
How long is the flight from Boston to Chicago?
A typical itinerary from Boston to Chicago takes about 3h 1m, including connections when the cheapest fare is not direct.
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November 2026