Route profile
SJC→MDW
Flight reliability, delays and best times to fly from San Jose to Chicago. · 1,838 miles
Right now
Current conditions at both ends of this route.
Aviation weather is not currently a factor. FAA operational data — ground stops, ground delay programs and closures — is not currently available to FlyerIntel.
Aviation weather is not currently a factor. FAA operational data — ground stops, ground delay programs and closures — is not currently available to FlyerIntel.
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 99% of comparable major US routes (4,577 compared)
Calculated from 1,642 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.
SJC → MDW flights departing 5–9 AM arrived on time 93.7% of the time, against 78.4% for 12–3 PM departures — a gap of 15.3 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 | 1,642 | 86.0% | 0.18% | -6 min | 2.2% |
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 Francisco 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 |
|---|---|---|---|---|---|
| SFO→ORD San Francisco to Chicago | 15,597 | 79.1% | 1.09% | -8 min | 67 |
| OAK→MDW Oakland to Chicago | 1,718 | 83.1% | 0.41% | -5 min | 84 |
| SJC→MDW this route San Jose to Chicago | 1,642 | 86.0% | 0.18% | -6 min | 91 |
| SFO→MDW San Francisco to Chicago | 1,186 | 75.4% | 0.67% | -2 min | 68 |
| SJC→ORD San Jose to Chicago | 990 | 92.3% | 0.81% | -11 min | 88 |
SJC → MDW is the most reliable pairing for this journey at 86.0% on time, against 79.1% for SFO → ORD.
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 Monday the least, a gap of 12.8 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 83.3% against 88.1% in the 12 months before — declining by 4.7 percentage points.
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 1,642 SJC → 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.