Flights Boston → Chicago
BOS → MDW
How long is the flight from Boston to Chicago?
The flight from Boston (BOS) to Chicago (MDW) takes 2h 18m on average. That is the median time recorded across 1 scheduled flight on this leg; the actual time varies by a few minutes with wind, routing and take-off queues.
Route overview
The flight route from Boston to Chicago operates with a Boeing 737-300 aircraft and has an on-time performance rate of 64%. Over the period in question, there were 295 total flights, each averaging a delay of 16.1 minutes. The destination airport sees nearly 20 million passengers annually, highlighting its significance as a major travel hub.
Your rights on this US flight (DOT)
US flights have no statutory cash compensation for delays. Under the US DOT rules, if your flight is cancelled or significantly changed and you decline rebooking, you're owed an automatic refund of the unused ticket. The tarmac-delay limit is 3 hours (domestic) / 4 hours (international). Amenities for controllable delays depend on each airline's contract of carriage.
US flight refund rules & checker →General information, not legal advice.
The Boston (BOS) → Chicago (MDW) route is operated by Southwest Airlines. Across 852 flights monitored in recent months, 61% arrived on time (within 15 min of schedule), with an average delay of 22 minutes. The cancellation rate is 2.82%. FlightGuard's average computed risk is 26.9/100 (medium), updated in real time from weather, ATC delays, strikes, NOTAMs, fuel and flight history. At Chicago the average ATFM delay is 5.5 minutes (main cause: atfm). Departing from Boston the average ATFM delay is 5.5 minutes.
Heading to Chicago: what to expect in this direction
Flying from Boston (BOS) to Chicago (MDW) heads west for about 1,381 km, a flight time of roughly 2h 18m.
Departures from Boston on this leg cluster in the morning window: about 38% of BOS-MDW flights take off then.
Air-traffic congestion: departing Boston the average ATFM delay is 5.5 min (atfm); arriving into Chicago it is 5.5 min (atfm).
Across 852 tracked BOS-MDW flights, 61% left on time with an average delay of 22 min and a 2.8% cancellation rate.
Route facts
Flights on this route
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Airline punctuality on this route
| Airline | On-time | Average delay | Cancellations |
|---|---|---|---|
| Southwest Airlines (WN) | 75% | 5 min | 0.3% |
Airlines operating BOS-MDW
Airports
Frequently asked questions about BOS-MDW
The flight from Boston (BOS) to Chicago (MDW) takes 2h 18m on average. That is the median time recorded across 1 scheduled flight on this leg; the actual time varies by a few minutes with wind, routing and take-off queues.
On the Boston (BOS) -> Chicago (MDW) route, on-time performance is 61% with an average delay of 22 minutes, based on 852 tracked flights.
The cancellation rate on Boston-Chicago is 2.82% across 852 monitored flights.
The route is operated by 1 airline: Southwest Airlines.
Enter your flight number on FlightGuard for a real-time analysis based on 9 factors: weather at Chicago, ATC delays, strikes, NOTAMs, fuel, airline punctuality and recent trends.
US flights have no statutory cash compensation for delays. Under US DOT rules, if the airline cancels or significantly changes your flight and you decline rebooking, you're owed an automatic refund of the unused ticket. The tarmac-delay limit is 3 hours (domestic) / 4 hours (international). Meals or hotels for controllable delays depend on each airline's contract of carriage.
