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Route Reliability

Boston → Chicago

BOS–MDW · 861 miles · Boston Logan International Airport to Chicago Midway International Airport

74
Usually Fine
WanderNerd Reliability Score
74%
Arrive within 15 minutes
10 min
Average arrival delay
1.5%
Cancelled
1,396
Flights in the data

Data through May 2026.

Southwest Airlines is the only airline in this data on this route, arriving on time 74% of the time across 1,396 flights. No comparison to make.

What the data says

Morning-you made the right choice.

BOS–MDW flights departing between 9 AM–12 PM arrived on time 94% of the time, versus 43% between 6–9 PM.

Skip Thursday if you can.

BOS–MDW flights arrived on time 82% of the time on Saturdays. On Thursdays: 68%.

Slipping a little lately.

BOS–MDW flights arrived on time 74% of the time over the last three months in the data, compared with 81% in the three months before that.

Flights on this route

The breakdown

On-time by weekday
  • Mon70%(205 flights)
  • Tue78%(181 flights)
  • Wed78%(180 flights)
  • Thu68%(203 flights)
  • Fri74%(214 flights)
  • Sat82%(179 flights)
  • Sun69%(208 flights)
On-time by departure window
  • 3–6 AM94%(252 flights)
  • 6–9 AM88%(198 flights)
  • 9 AM–12 PM94%(181 flights)
  • 12–3 PM79%(266 flights)
  • 3–6 PM50%(206 flights)
  • 6–9 PM43%(251 flights)
  • 9 PM–12 AM44%(16 flights)
On-time trend by month
74%
May

Jun 70% → May 74% on time

On-time arrival percentage by month
MonthOn-time percentageFlights
June 202570%157
July 202571%170
August 202581%133
September 202558%126
October 202571%138
November 202583%83
December 202573%90
January 202688%66
February 202681%58
March 202669%109
April 202681%118
May 202674%122

Same trip, other airports

Keep nerding

Based on 1,396 historical flights, because apparently we checked. Historical flight data: U.S. Bureau of Transportation Statistics, June 2025 – May 2026. Data through May 2026. How we calculate this.