Direct flights from Boston to Chicago BOS → MDW

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 $373. Arrivals run on time 75.4% at BOS and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Fares last checked 13 August 2026.

60-day flexibility overview based on 1 recent fares across the next 60 days

Cheapest
$373
Typical
$373
Most expensive
$373

Prices last updated 17 days ago. Fares change frequently — check the airline for current pricing.

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Southwest Airlines WN

Departure Schedule typical week

Typical weekly schedule · 32 flights per week (~5 per day) · Updated 53d ago

Southwest Airlines
32 flights per week (~5 per day)
Sat
05:15 07:45 15:25
Mon, Thu, Fri, Sat
05:25
Tue, Wed
05:35 13:25
Daily
07:30
Sun, Mon, Thu, Fri, Sat
13:10
Sun
16:45 19:05 22:05
Mon, Tue, Wed, Thu, Fri, Sat
18:45

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 → MCO Orlando 5 airlines BOS → DFW Dallas-Fort Worth 4 airlines BOS → LAX Los Angeles 4 airlines BOS → RDU Raleigh/Durham 4 airlines

Frequently asked questions

Is there a direct flight from Boston to Chicago?

Yes, Southwest Airlines operates nonstop flights from Boston (BOS) to Chicago (MDW).

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 multiple daily — 32 flights per week (~5 per day).

What is the on-time performance for flights from Boston to Chicago?

Arrivals run on time 75.4% at BOS and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.

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 $373, with a typical fare around $373. Based on 1 recent fare combinations.

Explore More

BOS All direct flights from Boston MDW All direct flights from Chicago MDW → BOS Return: Chicago to Boston

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