Cheap flights from Boston to Chicago
From 185 USD — compare hundreds of airlines
About this route
Compare flights from Boston to Chicago, a about 1,366 km route (around 2h 12m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as American Airlines, Alaska Airlines, jetBlue operate this route.
Prices by date
Airlines on this route
FAQ
What's the cheapest month to fly Boston to Chicago?
It's usually 2026-08, from 105 USD. Use the price calendar to compare other dates.
How long is the flight from Boston to Chicago?
A nonstop flight takes about 2h 12m and covers around 1,366 km. Connecting itineraries take longer.
Are there direct flights from Boston to Chicago?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Boston to Chicago?
American Airlines, Alaska Airlines, jetBlue, Spirit Airlines operate this route, among others. Compare them all in the results.
When should I book Boston–Chicago flights?
As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.