Direct flights from Chicago Midway to Boston
33 nonstop flights a week on 1 airline. Zero layovers — one hop from MDW to BOS.
Flight time: about 1h44m nonstop
Which days does it fly?
When does it fly?
Departure times in Chicago Midway local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA4611 | 5:31a | 1h43m | Sun |
| Southwest SWA4611 | 5:39a | 1h41m | Sat |
| Southwest SWA1405 | 7:49a | 1h44m | Sun |
| Southwest SWA4611 | 7:50a | 1h45m | Mon, Thu, Fri |
| Southwest SWA4611 | 7:58a | 1h53m | Tue |
| Southwest SWA4611 | 8:20a | 1h40m | Wed |
| Southwest SWA356 | 8:25a | 1h41m | Sat |
| Southwest SWA1405 | 9:23a | 1h52m | Tue |
| Southwest SWA1405 | 9:40a | 1h47m | Mon, Wed, Thu, Fri |
| Southwest SWA1498 | 12:36p | 1h44m | Sun |
| Southwest SWA4716 | 12:57p | 1h50m | Mon |
| Southwest SWA2641 | 12:58p | 1h39m | Wed |
| Southwest SWA4716 | 1:16p | 1h42m | Thu–Fri |
| Southwest SWA4975 | 1:53p | 1h46m | Sun |
| Southwest SWA2641 | 1:59p | 1h40m | Tue |
| Southwest SWA3456 | 2:15p | 1h48m | Sat |
| Southwest SWA4975 | 3:47p | 1h37m | Wed |
| Southwest SWA4975 | 4:42p | 1h53m | Fri |
| Southwest SWA4975 | 5:26p | 1h39m | Thu |
| Southwest SWA1374 | 6:20p | 1h48m | Wed |
| Southwest SWA4975 | 6:24p | 1h41m | Mon |
| Southwest SWA1374 | 6:58p | 1h54m | Tue |
| Southwest SWA3521 | 7:17p | 1h51m | Sun |
| Southwest SWA4975 | 7:19p | 1h42m | Sat |
| Southwest SWA232 | 8:42p | 1h43m | Mon, Thu |
| Southwest SWA232 | 11:23p | 1h46m | Fri |
Southwest
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The route
One hop: MDW → BOSDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Chicago Midway (MDW) to Boston (BOS)
Chicago Midway International Airport (MDW) has 33 nonstop flights a week to Boston (BOS), operated by Southwest. No layovers, no connections — one hop out of MDW and you're there.
This route flies every day of the week, so any travel day works. Route data updated July 2026 from observed departures.
Route data updated July 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from Chicago Midway to Boston?
The nonstop flight from Chicago Midway (MDW) to Boston (BOS) takes about 1h44m in the air, based on recently observed nonstop departures.
How long does it take to drive from Chicago Midway to Boston?
Driving from Chicago Midway to Boston takes about 14h 43m, covering roughly 983 miles. The nonstop flight takes about 1h44m.