Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from Boston to Chicago is JetBlue Airways.
Cheapest Month
October
Travel Period: February 2025 - January 2026
The cheapest month(s) to fly from Boston to Chicago is October.
Cheapest Day of the Week
Monday
The cheapest day(s) of the week to fly from Boston to Chicago is Monday.
What’s the most popular airline flying from Boston to Chicago?
The most popular airline flying from Boston to Chicago is American Airlines. Find the latest flight deals on Wego.
How far is Chicago from Boston?
The flight distance between Boston and Chicago is 1366km. Check all available flights on Wego.
Popular Airlines Flying From Boston to Chicago
Popular Destinations From Chicago
Popular Destinations From Boston
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel Central Loop
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel
