Chicago (MDW) to Boston (BOS) flights
Southwest Airlines flies nonstop from Chicago Midway International Airport to Boston Logan International Airport, with about 33 flights a week in July 2026. The 861-mile flight takes about 2h 10m gate to gate.
- Distance
- 861 mi · 1,386 km
- Flight time
- 2h 10m
- Airlines
- 1
- Seats filled
- 87%
Airlines flying MDW to BOS
| 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 | 199,174 | 2h 10m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
MDW to BOS flight schedule
13 flight numbers flew this route in August 2026, 2 of them almost daily. The first usually leaves at 5:45am and the last at 6:30pm. 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 3094Southwest Airlines | 5:45am | 9:00am | 12 | 91% |
| WN 1677Southwest Airlines | 6:40am | 9:55am | 8 | n/a |
| WN 2681Southwest Airlines | 7:40am | 11:00am | 8 | n/a |
| WN 3473Southwest Airlines | 7:55am | 11:25am | 4 | n/a |
| WN 3315Southwest Airlines | 8:15am | 11:40am | 24 | 79% |
| WN 1165Southwest Airlines | 11:25am | 2:45pm | 4 | n/a |
| WN 573Southwest Airlines | 11:35am | 2:55pm | 12 | 64% |
| WN 562Southwest Airlines | 12:05pm | 3:25pm | 4 | n/a |
| WN 4860Southwest Airlines | 12:50pm | 4:10pm | 8 | n/a |
| WN 4215Southwest Airlines | 2:35pm | 5:55pm | 20 | 58% |
| WN 3329Southwest Airlines | 3:10pm | 6:30pm | 8 | n/a |
| WN 4180Southwest Airlines | 5:55pm | 9:20pm | 4 | n/a |
| WN 1181Southwest Airlines | 6:30pm | 9:50pm | 12 | 42% |
Is MDW to BOS on time?
From September 2025 to August 2026, 66% of 1,368 flights arrived within 15 minutes of schedule and 1.3% were cancelled. Flights leaving around 6am were the most punctual (94%), those around 7pm the least (49%). Most delay time was caused by air traffic control and airport congestion (37%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,368 | 66% | 23 min | 1.3% |
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 | 47 | 94% | |
| 6am to 7am | 70 | 94% | |
| 7am to 8am | 142 | 91% | |
| 8am to 9am | 42 | 81% | |
| 9am to 10am | 168 | 84% | |
| 10am to 11am | 30 | 80% | |
| 11am to 12pm | 42 | 58% | |
| 12pm to 1pm | 126 | 54% | |
| 1pm to 2pm | 102 | 52% | |
| 2pm to 3pm | 101 | 52% | |
| 3pm to 4pm | 68 | 46% | |
| 4pm to 5pm | 58 | 30% | |
| 5pm to 6pm | 72 | 63% | |
| 6pm to 7pm | 164 | 61% | |
| 7pm to 8pm | 109 | 49% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 134 | 21,363 | |
| September 2025 | 128 | 19,474 | |
| October 2025 | 138 | 20,194 | |
| November 2025 | 85 | 12,710 | |
| December 2025 | 91 | 12,703 | |
| January 2026 | 67 | 9,218 | |
| February 2026 | 60 | 7,997 | |
| March 2026 | 112 | 15,913 | |
| April 2026 | 119 | 16,511 | |
| May 2026 | 123 | 19,097 | |
| June 2026 | 141 | 21,347 | |
| July 2026 | 147 | 22,647 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.