Direct flights from Boston to Chicago

  • ~5 flights a day
  • 2 airlines

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When the nonstops leave

Typical weekly schedule · 32 flights per week (~5 per day) · Updated 103d ago

Morning before noon 15 a week
5:15 AMSat 5:25 AM4 days a week 5:35 AMTue, Wed 7:30 AM 7:45 AMSat
Afternoon noon – 6 PM 9 a week
1:10 PM5 days a week 1:25 PMTue, Wed 3:25 PMSat 4:45 PMSun
Evening after 6 PM 8 a week
6:45 PMnot Sun 7:05 PMSun 10:05 PMSun
Southwest Airlines

More nonstops from Boston

BOS → MIA Miami 6 airlines BOS → ORD Chicago 6 airlines BOS → DEN Denver 5 airlines BOS → LHR London 5 airlines BOS → DFW Dallas-Fort Worth 4 airlines BOS → LAX Los Angeles 4 airlines BOS → RDU Raleigh/Durham 4 airlines BOS → SAN San Diego 4 airlines MDW → BOS The return trip BOS All nonstops from Boston MDW All nonstops from Chicago

Frequently asked questions

Is there a direct flight from Boston to Chicago?

Yes. Southwest Airlines flies nonstop from Boston (BOS) to Chicago (MDW), several times daily. The flight takes about 2h 16m and covers 858 miles (1,381 km). Round-trip fares typically run around $315. Fares last checked 8 October 2026.

Which airlines fly direct from Boston to Chicago?

Southwest Airlines operates nonstop flights from Boston to Chicago.

How long is the flight from Boston to Chicago?

The nonstop flight from Boston to Chicago takes ~2h 16m (approximately 1381 km).

How often do direct flights operate from Boston to Chicago?

Nonstop flights from Boston to Chicago operate several times daily — 32 flights per week (~5 per day).

What days of the week are there direct flights from Boston to Chicago?

Direct flights from Boston to Chicago operate every day of the week.

How much is a round-trip flight from Boston to Chicago?

Round-trip flights from Boston (BOS) to Chicago (MDW) start at $315, with a typical fare around $315. Based on 1 recent fare combinations.