Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Chicago to Boston is JetBlue Airways.
Cheapest Month
March
Travel Period: February 2025 - January 2026
The cheapest month(s) to fly from Chicago to Boston is March.
Cheapest Day of the Week
Tuesday
The cheapest day(s) of the week to fly from Chicago to Boston is Tuesday.
What’s the most popular airline flying from Chicago to Boston?
The most popular airline flying from Chicago to Boston is American Airlines. Find the latest flight deals on Wego.
How far is Boston from Chicago?
The flight distance between Chicago and Boston is 1366km. Check all available flights on Wego.