Open interactive map →Cheap flights from Boston to Chicago
Fares on the Boston to Chicago route vary noticeably by season and demand. Right now the lowest available price is €112. Non-stop flights are available, making it a convenient option if you want to skip layovers. 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 Boston tend to be cheaper than Friday or Sunday flights. If €112 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€112DirectCheapest
Based on tracked fares, October is the cheapest month to fly this route at around €112.
Prices last updated: September 2026
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 →
About Chicago
Chicago is the great American city that the coasts overlook - a dense, architecturally extraordinary lakefront city with world-class museums, deep-dish pizza, and jazz and blues venues that trace the music's northern migration. O'Hare (ORD) and Midway (MDW) together give the city one of the world's widest airport choices.
Alternative routes
Other ways to reach Chicago
Frequently asked questions
How much does a flight from Boston to Chicago cost?
The cheapest fare currently available from Boston to Chicago is €112. 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 Boston to Chicago?
Yes - non-stop flights are currently available from Boston to Chicago. The cheapest direct fare starts at €112, making it a convenient option if you want to avoid layover time. Direct flights are generally quicker and less stressful, especially for shorter trips to United States. Click through to the booking site to check live availability and schedules for your dates.
When is the cheapest time to fly from Boston to Chicago?
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 Boston. 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.