Open interactive map →Cheap flights from Chicago to Boston
Fares on the Chicago to Boston route vary noticeably by season and demand. Right now the lowest available price is €115. The route offers both direct and connecting options depending on the date. Booking further in advance typically unlocks lower prices, especially around school holidays and peak travel months. The calendar below maps out the cheapest and most expensive months so you can plan before committing to dates.
For the best prices on this route, aim to book at least 3-4 weeks in advance. Tuesday and Wednesday departures from Chicago tend to be cheaper than Friday or Sunday flights. If €115 is above your budget, try adjusting to a shoulder-season month using the calendar above - fares can drop significantly outside peak periods.
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Cheapest month to fly
- October 2026€1151 stopCheapest
Based on tracked fares, October is the cheapest month to fly this route at around €115.
Prices last updated: September 2026
October in Boston
Avg 14°C~8 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 fare currently available from Chicago to Boston is €115. Prices on this route vary by season, day of week, and how far in advance you book. The month-by-month price calendar on this page shows exactly when fares are highest and lowest, so you can pick the most cost-effective window before searching for specific dates. Fares are refreshed regularly as our flight partners publish new availability.
Are there direct flights from Chicago to Boston?
SkyHopp tracks both direct and connecting flights from Chicago to Boston. Connecting flights are often priced lower but add travel time due to the layover. Whether a non-stop option exists on specific dates depends on airline schedules - use the "Direct only" filter on the interactive map to see non-stop options, or check the booking site for a full breakdown by stop count.
When is the cheapest time to fly from Chicago to Boston?
Prices on this route typically dip during shoulder-season months, away from school holidays and public holiday windows. Mid-week departures - particularly Tuesday to Thursday - tend to be cheaper than flights on Fridays and Sundays from Chicago. The month-by-month price calendar above is the fastest way to identify the cheapest window - look for the months with the lowest fares before committing to travel dates. Booking 3-6 weeks in advance generally offers the best balance of price and seat availability on this route.