Direct flights from Chicago Midway to Boston
32 nonstop flights a week on 1 airline. Zero layovers — one hop from MDW to BOS.
Flight time: about 1h50m 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 SWA3094 | 5:52a | 1h46m | Mon, Fri |
| Southwest SWA3094 | 5:56a | 1h46m | Thu |
| Southwest SWA2681 | 6:00a | 1h52m | Sun |
| Southwest SWA1677 | 6:47a | 1h49m | Tue |
| Southwest SWA2681 | 7:47a | 1h49m | Sat |
| Southwest SWA3473 | 8:04a | 1h55m | Sun |
| Southwest SWA1677 | 8:15a | 1h55m | Wed |
| Southwest SWA3315 | 8:31a | 1h42m | Thu–Fri |
| Southwest SWA3315 | 8:40a | 1h44m | Mon |
| Southwest SWA3315 | 9:14a | 1h50m | Tue |
| Southwest SWA3315 | 9:21a | 1h50m | Wed |
| Southwest SWA3315 | 9:39a | 2h2m | Sat |
| Southwest SWA573 | 12:04p | 2h3m | Fri |
| Southwest SWA573 | 12:10p | 2h9m | Mon |
| Southwest SWA573 | 12:31p | 1h49m | Thu |
| Southwest SWA1165 | 12:42p | 2h11m | Sat |
| Southwest SWA4860 | 1:15p | 1h51m | Tue |
| Southwest SWA4860 | 2:00p | 1h49m | Wed |
| Southwest SWA562 | 2:01p | 1h51m | Sun |
| Southwest SWA4215 | 3:29p | 1h52m | Fri |
| Southwest SWA3329 | 3:30p | 1h50m | Sat |
| Southwest SWA4215 | 3:40p | 1h36m | Thu |
| Southwest SWA4215 | 5:03p | 2h4m | Mon |
| Southwest SWA4215 | 6:23p | 2h20m | Tue |
| Southwest SWA1181 | 6:41p | 1h47m | Mon |
| Southwest SWA4215 | 7:06p | 1h38m | Wed |
| Southwest SWA1181 | 7:07p | 1h53m | Fri |
| Southwest SWA3329 | 7:14p | 1h38m | Sun |
| Southwest SWA4180 | 8:51p | 1h40m | Sun |
| Southwest SWA1181 | 8:59p | 1h40m | Thu |
SouthwestThe 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 32 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 September 2026 from observed departures.
Route data updated September 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 1h50m 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 1h50m.