Boston (BOS) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Boston Logan International Airport to Chicago Midway International Airport, with about 33 flights a week in July 2026. The 861-mile flight takes about 2h 34m gate to gate.
- Distance
- 861 mi · 1,386 km
- Flight time
- 2h 34m
- Airlines
- 1
- Seats filled
- 85%
Airlines flying BOS to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 33 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 188,870 | 2h 34m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
BOS to MDW flight schedule
13 flight numbers flew this route in August 2026, 3 of them almost daily. The first usually leaves at 7:30am and the last at 9:05pm. Times are local and can change; check with the airline before you book.
| Flight | Departs | Arrives | Days flown in August 2026 | On time (12 months) |
|---|---|---|---|---|
| WN 744Southwest Airlines | 7:30am | 9:05am | 28 | 93% |
| WN 175Southwest Airlines | 8:40am | 10:15am | 4 | n/a |
| WN 1585Southwest Airlines | 9:25am | 11:00am | 4 | n/a |
| WN 1645Southwest Airlines | 10:05am | 11:35am | 8 | n/a |
| WN 2421Southwest Airlines | 12:40pm | 2:10pm | 12 | 83% |
| WN 4298Southwest Airlines | 1:00pm | 2:35pm | 4 | n/a |
| WN 4657Southwest Airlines | 1:55pm | 3:25pm | 4 | n/a |
| WN 3480Southwest Airlines | 3:25pm | 5:00pm | 4 | n/a |
| WN 672Southwest Airlines | 3:55pm | 5:30pm | 20 | 30% |
| WN 3738Southwest Airlines | 5:35pm | 7:15pm | 4 | n/a |
| WN 746Southwest Airlines | 6:40pm | 8:20pm | 23 | 52% |
| WN 3183Southwest Airlines | 8:20pm | 10:00pm | 12 | 40% |
| WN 2662Southwest Airlines | 9:05pm | 10:40pm | 4 | n/a |
Is BOS to MDW on time?
From September 2025 to August 2026, 70% of 1,368 flights arrived within 15 minutes of schedule and 2% were cancelled. Flights leaving around 10am were the most punctual (92%), those around 5pm the least (32%). Most delay time was caused by late-arriving aircraft (58%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,368 | 70% | 20 min | 2% |
Airlines as sold: flights operated by regional partners count under the airline on the ticket. Average delay is across all completed flights, early arrivals counted as zero.
On-time arrivals by departure time
| Scheduled departure | Flights | On time, relative | On time |
|---|---|---|---|
| 5am to 6am | 227 | 91% | |
| 7am to 8am | 167 | 91% | |
| 9am to 10am | 43 | 88% | |
| 10am to 11am | 92 | 92% | |
| 11am to 12pm | 29 | 86% | |
| 12pm to 1pm | 48 | 75% | |
| 1pm to 2pm | 141 | 69% | |
| 2pm to 3pm | 86 | 81% | |
| 3pm to 4pm | 103 | 45% | |
| 4pm to 5pm | 56 | 57% | |
| 5pm to 6pm | 69 | 32% | |
| 6pm to 7pm | 185 | 43% | |
| 7pm to 8pm | 35 | 42% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 133 | 20,296 | |
| September 2025 | 126 | 17,378 | |
| October 2025 | 138 | 20,800 | |
| November 2025 | 83 | 12,259 | |
| December 2025 | 90 | 13,031 | |
| January 2026 | 66 | 7,593 | |
| February 2026 | 58 | 7,283 | |
| March 2026 | 109 | 14,032 | |
| April 2026 | 118 | 16,847 | |
| May 2026 | 122 | 17,568 | |
| June 2026 | 138 | 19,558 | |
| July 2026 | 147 | 22,225 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.