Open interactive map →Cheap flights from Chicago to Boston
Fares on the Chicago to Boston route are tracked month by month. The lowest observed price is €135. The cheapest tracked fare is non-stop. The calendar below lists the months SkyHopp has fares for - not enough months yet to name a cheapest month.
SkyHopp's cheapest tracked fare from Chicago to Boston is €135. The cheapest tracked fare is non-stop. The calendar above lists the months with data; more months are needed before naming a cheapest month.
Flying the other way? Cheap flights from Boston to Chicago.
One-way fares
From €135
Cheapest tracked fare (non-stop)
Return fares
From €272
Tracked return fares (out 21 Nov 2026, back 22 Nov 2026)
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Cheapest month to fly
- November 2026€135DirectCheapest
SkyHopp has tracked fares for this route in November at around €135. That is the only month with data so far, so it is too early to name a cheapest month.
Cheapest fare last seen 25 October 2026.
November in Boston
Avg 5°C~5 rainy days
Historical averages from Open-Meteo. Shown for the cheapest travel month.
Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
Alternative routes
Other ways to reach Boston
Frequently asked questions
How much does a flight from Chicago to Boston cost?
The cheapest tracked fare from Chicago to Boston is €135. The month-by-month price calendar on this page lists the months SkyHopp has fares for. A tracked return fare on this pair is currently from €272. Fares are refreshed as our flight partners publish new availability.
Are there direct flights from Chicago to Boston?
Yes - non-stop fares appear in SkyHopp's tracked data from Chicago to Boston. The cheapest tracked fare, from €135, is itself non-stop. Click through to the booking site to check schedules for your dates.
When is the cheapest time to fly from Chicago to Boston?
SkyHopp does not yet have enough months of fares on this route to name a cheapest month. The calendar above lists the months that already have data. Set a price alert on this page to watch the fare.