Flight Check

Best Airline: MDW to BOS

Chicago to Boston — airline reliability comparison

Southwest Airlines is the most reliable airline on the MDW to BOS route with a 74% on-time rate. Based on 4,882 flights tracked.

This route involves weather-prone airports, which can affect reliability regardless of airline.

Source: Bureau of Transportation Statistics. Updated October 2026.

On-Time Rate by Airline

Southwest Airlines74%

MDW to BOS Airline Comparison

AirlineOn-Time %Cancel %Avg DelayFlights
Southwest AirlinesWNBest74%1.4%58m4,882

Route Overview

73%
Overall On-Time
59m
Avg Delay
1.2%
Cancel Rate
4,882
Total Flights
MDW to BOS Route DetailsReturn: BOS to MDW
MDW AirportBOS Airport

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Data last updated October 2026. Source: Bureau of Transportation Statistics.