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Route Reliability

Chicago → San Juan

MDW–SJU · 2,057 miles · Chicago Midway International Airport to Luis Muñoz Marín International Airport

60
A Little Dicey
WanderNerd Reliability Score
64%
Arrive within 15 minutes
18 min
Average arrival delay
1.9%
Cancelled
53
Flights in the data

Data through May 2026.

Southwest Airlines is the only airline in this data on this route, arriving on time 64% of the time across 53 flights. No comparison to make.

What the data says

Any day works.

Weekday differences are small here: 63% to 64% on time across the week.

Flights on this route

The breakdown

On-time by weekday
  • Mon—(0 flights)
  • Tue—(0 flights)
  • Wed—(0 flights)
  • Thu—(0 flights)
  • Fri—(0 flights)
  • Sat63%(38 flights)
  • Sun64%(14 flights)

Same trip, other airports

Keep nerding

Based on 53 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.