Flights from Boston to Chicago Midway

BOSMDW

Boston Logan International Airport (Boston, United States) → Chicago Midway International Airport (Chicago, United States)

Nonstop
2h 45m
Distance
1,381 km
Frequency
7×/week
One-way from
$125
Airlines
Southwest Airlines
Book on Aviasales

Fares by month

One-way, per person

Lowest fares Aviasales travelers found in recent searches; some may include a connection. Prices change often — tap a month to see live fares.

Weekly schedule

Monday

  • WN218507:05→08:502h 45mSouthwest Airlines
  • WN81312:45→14:302h 45mSouthwest Airlines
  • WN275816:20→18:052h 45mSouthwest Airlines
  • WN81618:30→20:152h 45mSouthwest Airlines

Tuesday

  • WN81312:50→14:402h 50mSouthwest Airlines
  • WN81617:55→19:402h 45mSouthwest Airlines

Wednesday

  • WN81312:50→14:402h 50mSouthwest Airlines
  • WN81617:55→19:402h 45mSouthwest Airlines

Thursday

  • WN218507:05→08:502h 45mSouthwest Airlines
  • WN81312:45→14:302h 45mSouthwest Airlines
  • WN275816:20→18:052h 45mSouthwest Airlines
  • WN81618:30→20:152h 45mSouthwest Airlines

Friday

  • WN218507:05→08:502h 45mSouthwest Airlines
  • WN81312:45→14:302h 45mSouthwest Airlines
  • WN275816:20→18:052h 45mSouthwest Airlines
  • WN81618:30→20:152h 45mSouthwest Airlines

Saturday

  • WN275815:10→16:552h 45mSouthwest Airlines

Sunday

  • WN218507:05→08:502h 45mSouthwest Airlines
  • WN81312:45→14:302h 45mSouthwest Airlines
  • WN275816:20→18:052h 45mSouthwest Airlines
  • WN81618:30→20:152h 45mSouthwest Airlines

Boston to Chicago Midway — frequently asked

How long is the flight from Boston to Chicago Midway?
BOS–MDW is 2h 45m nonstop, covering 1,381 km (858 mi).
Which airlines fly nonstop from Boston to Chicago Midway?
Southwest Airlines operates this route nonstop.
How much is a flight from Boston to Chicago Midway?
One-way fares on BOS–MDW recently started from $125 ($149 nonstop). The lowest recent fare is for travel in November 2026. Fares change daily, so check current prices before booking.
How often do flights run from Boston to Chicago Midway?
The route is served 7 days a week (21 scheduled departures).