Flight Check

Best Airline: BOS to MDW

Boston to Chicago — airline reliability comparison

Southwest Airlines is the most reliable airline on the BOS to MDW route with a 78% on-time rate. Based on 4,855 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 Airlines78%

BOS to MDW Airline Comparison

AirlineOn-Time %Cancel %Avg DelayFlights
Southwest AirlinesWNBest78%1.7%62m4,855

Route Overview

77%
Overall On-Time
63m
Avg Delay
1.5%
Cancel Rate
4,855
Total Flights
BOS to MDW Route DetailsReturn: MDW to BOS
BOS AirportMDW Airport

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