Cheap flights from Chicago to Boston
Flights from Chicago to Boston 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: 2h 48m
Key facts
- Lowest fare
- €79 · Wed 4 Nov
- Direct flights
- Yes
- Flight time
- 2h 48m
- Airlines
- Southwest Airlines, Frontier Airlines, jetBlue, United Airlines
- Cheapest month
- November 2026
- Distance
- 1369 km
Round trip
One way
Questions people ask before they book
How much are flights from Chicago to Boston?
The lowest fare we currently show from Chicago to Boston is €79 for one adult. That price is tied to specific dates and can sell out.
Are there direct flights from Chicago to Boston?
Yes. Direct flights from Chicago to Boston show up in current fares. Filter by Direct when you search to hide connections.
Which airlines fly from Chicago to Boston?
Airlines showing fares on this route include Southwest Airlines, Frontier Airlines, jetBlue, United Airlines, American Airlines. The cheapest airline is not always the one with a bag included.
How long is the flight from Chicago to Boston?
A typical itinerary from Chicago to Boston takes about 2h 48m, including connections when the cheapest fare is not direct.
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November 2026