Route profile
SAN→MDW
Flight reliability, delays and best times to fly from San Diego to Chicago. · 1,728 miles
Right now
Current conditions at both ends of this route.
Aviation weather is not currently a factor.
Aviation weather is not currently a factor.
Airport conditions describe the airfield, not any individual flight. An airport operating normally is not a guarantee that a specific flight will depart on time.
Route reliability
July 2023 – June 2026
Better than 64% of comparable major US routes (4,577 compared)
Calculated from 3,168 flights. How this is calculated
Source: US DOT Bureau of Transportation Statistics · Data covering July 2023 – June 2026
Best time to fly
On-time arrival rate by scheduled local departure time.
SAN → MDW flights departing 5–9 AM arrived on time 91.0% of the time, against 63.9% for 6–9 PM departures — a gap of 27.1 percentage points.
By departure window
By departure hour
Source: FlyerIntel analysis of US DOT BTS data · July 2023 – June 2026 · Buckets with fewer than 120 flights are not scored.
Airlines on this route
Performance by the carrier that actually operated the flight.
| Carrier | Flights | On time | Cancelled | Median delay | Severe |
|---|---|---|---|---|---|
| Southwest Airlines | 3,168 | 78.0% | 0.82% | -3 min | 5.6% |
Source: FlyerIntel analysis of US DOT BTS data · July 2023 – June 2026 · Carriers with fewer than 200 flights on this route are not listed.
Other ways to fly San Diego to Chicago
Airport pairs serving the same journey, grouped by the DOT's own city-market definition. They do not perform the same way.
| Route | Flights | On time | Cancelled | Median delay | Score |
|---|---|---|---|---|---|
| SAN→ORD San Diego to Chicago | 9,463 | 82.1% | 1.14% | -9 min | 70 |
| SAN→MDW this route San Diego to Chicago | 3,168 | 78.0% | 0.82% | -3 min | 71 |
Source: FlyerIntel analysis of US DOT BTS data · July 2023 – June 2026 · Grouped by DOT city market, which places Newark with the New York airports and Baltimore with the Washington ones.
Weekly and seasonal patterns
By day of week
Saturday is historically the most reliable day and Sunday the least, a gap of 12.5 percentage points.
By month
July is historically the weakest month and November the strongest, a spread of 14.0 percentage points.
Historical trend
On-time arrival rate by month.
Over the most recent 12 months (2025-07 to 2026-06), on-time arrivals averaged 78.1% against 77.1% in the 12 months before — broadly unchanged.
Source: FlyerIntel analysis of US DOT BTS data · July 2023 – June 2026
Data and methodology
All figures on this page are calculated by FlyerIntel from 3,168 SAN → MDW flight records published by the US DOT Bureau of Transportation Statistics, covering July 2023 – June 2026. A flight is counted as delayed when it arrives 15 or more minutes after its scheduled arrival time, following BTS methodology. Cancelled and diverted flights have no arrival time and are excluded from on-time rates rather than counted as late.