Direct flights from Boston to Chicago BOS → ORD
American Airlines, Delta Air Lines, JetBlue Airways and United Airlines operate nonstop flights from Boston (BOS) to Chicago (ORD). The nonstop flight takes around ~1h 44m, covering 864 miles (1,391 km) and operates multiple daily. Round-trip fares currently start at $165, with a typical fare around $251 across 220 recent fare combinations. Updated 28 June 2026.
60-day flexibility overview based on 220 recent fares across the next 60 days
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American Airlines
AA
Delta Air Lines
DL
JetBlue Airways
B6
United Airlines
UA
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Frequently asked questions
Is there a direct flight from Boston to Chicago?
Yes, American Airlines, Delta Air Lines and 2 more airlines operate nonstop flights from Boston (BOS) to Chicago (ORD).
Which airlines fly direct from Boston to Chicago?
American Airlines, Delta Air Lines, JetBlue Airways, United Airlines operate nonstop flights from Boston to Chicago.
How long is the flight from Boston to Chicago?
The nonstop flight from Boston to Chicago takes ~1h 44m (approximately 1391 km).
How often do direct flights operate from Boston to Chicago?
Nonstop flights from Boston to Chicago operate multiple daily.
How much is a round-trip flight from Boston to Chicago?
Round-trip flights from Boston (BOS) to Chicago (ORD) start at $165, with a typical fare around $251. Based on 220 recent fare combinations.