Direct flights from Boston to Chicago
34 nonstop flights a week on 1 airline. Zero layovers — one hop from BOS to MDW.
Flight time: about 2h6m nonstop
Which days does it fly?
When does it fly?
Departure times in Boston local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA3911 | 12:53a | 2h1m | Tue |
| Southwest SWA3239 | 5:32a | 2h5m | Mon, Thu, Fri |
| Southwest SWA3054 | 5:39a | 2h | Tue–Wed |
| Southwest SWA3239 | 6:31a | 2h11m | Sat |
| Southwest SWA745 | 7:42a | 2h3m | Tue, Sun |
| Southwest SWA745 | 7:46a | 2h4m | Mon, Wed, Thu, Fri |
| Southwest SWA745 | 8:33a | 2h6m | Sat |
| Southwest SWA746 | 1:23p | 2h8m | Thu |
| Southwest SWA746 | 1:30p | 2h10m | Fri, Sun |
| Southwest SWA320 | 1:47p | 2h4m | Tue–Wed |
| Southwest SWA746 | 2:34p | 2h2m | Mon |
| Southwest SWA746 | 3:36p | 2h8m | Sat |
| Southwest SWA4106 | 3:56p | 2h6m | Wed |
| Southwest SWA4106 | 4:44p | 1h57m | Tue |
| Southwest SWA2777 | 5:17p | 2h6m | Sun |
| Southwest SWA4106 | 5:38p | 2h5m | Mon, Fri |
| Southwest SWA3911 | 6:13p | 2h6m | Wed |
| Southwest SWA4106 | 6:37p | 2h11m | Thu |
| Southwest SWA3911 | 7:08p | 2h | Tue |
| Southwest SWA3911 | 7:33p | 2h12m | Fri |
| Southwest SWA3287 | 7:39p | 2h5m | Sun |
| Southwest SWA3911 | 8:04p | 2h7m | Thu |
| Southwest SWA3911 | 8:05p | 2h16m | Sat |
| Southwest SWA585 | 11:15p | 2h3m | Sun |
Southwest
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The route
One hop: BOS → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Boston (BOS) to Chicago (MDW)
Boston Logan International Airport (BOS) has 34 nonstop flights a week to Chicago (MDW), operated by Southwest. No layovers, no connections — one hop out of BOS 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 Boston to Chicago?
The nonstop flight from Boston (BOS) to Chicago (MDW) takes about 2h6m in the air, based on recently observed nonstop departures.
How long does it take to drive from Boston to Chicago?
Driving from Boston to Chicago takes about 14h 43m, covering roughly 983 miles. The nonstop flight takes about 2h6m.