Direct flights from Boston to Chicago
32 nonstop flights a week on 1 airline. Zero layovers — one hop from BOS to MDW.
Flight time: about 2h13m 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 SWA744 | 7:18a | 2h20m | Sat |
| Southwest SWA744 | 7:40a | 2h14m | Mon, Tue, Wed, Thu, Fri, Sun |
| Southwest SWA175 | 9:04a | 2h4m | Sat |
| Southwest SWA1585 | 9:44a | 2h20m | Sun |
| Southwest SWA1645 | 10:18a | 2h14m | Tue–Wed |
| Southwest SWA2421 | 12:50p | 2h16m | Thu–Fri |
| Southwest SWA2421 | 12:56p | 2h8m | Mon |
| Southwest SWA4298 | 1:35p | 2h22m | Sat |
| Southwest SWA4657 | 2:08p | 2h2m | Sun |
| Southwest SWA746 | 3:37p | 2h18m | Wed |
| Southwest SWA746 | 3:56p | 2h4m | Tue |
| Southwest SWA672 | 4:12p | 2h9m | Mon, Thu |
| Southwest SWA3480 | 4:36p | 2h17m | Sat |
| Southwest SWA672 | 6:03p | 2h24m | Fri |
| Southwest SWA3738 | 6:40p | 2h7m | Sun |
| Southwest SWA746 | 7:12p | 2h33m | Thu |
| Southwest SWA746 | 7:16p | 2h5m | Fri |
| Southwest SWA672 | 7:34p | 2h10m | Wed |
| Southwest SWA672 | 8:04p | 2h4m | Tue |
| Southwest SWA4010 | 8:05p | 2h12m | Sun |
| Southwest SWA3183 | 8:54p | 2h6m | Fri |
| Southwest SWA3183 | 9:18p | 2h10m | Mon |
| Southwest SWA746 | 9:34p | 2h14m | Mon |
| Southwest SWA3183 | 9:58p | 2h40m | Thu |
Southwest
Find fares 🥕
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 32 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 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 Boston to Chicago?
The nonstop flight from Boston (BOS) to Chicago (MDW) takes about 2h13m 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 2h13m.