Route profile
MDW→OAK
Flight reliability, delays and best times to fly from Chicago to Oakland, 1,844 miles.
Right now
Aviation weather is not currently a factor.
Aviation weather is not currently a factor.
Route reliability
July 2023 – July 2026
Better than 38% of comparable major US routes (4,598 compared)
Calculated from 1,785 flights. How this is calculated · What counts as on time
MDW → OAK arrives on time 71.4% of the time; the return trip, OAK → MDW, arrives on time 83.1% of the time, an 11.7-point gap between the two directions of the same city pair.
MDW → OAK spends 21.0 minutes on the ground on a 1,844-mile trip: 15.2 minutes from pushback to wheels-up at MDW and 5.8 minutes from touchdown to gate at OAK.
Source: US DOT Bureau of Transportation Statistics · Data covering July 2023 – July 2026
What stands out
On-time performance swings unusually widely by time of day here, wider than 97% of 4,023 comparable routes.
84.8% on time for 5–9 AM departures, against 49.3% for 9 PM–5 AM.
Source: FlyerIntel analysis of US DOT BTS data · July 2023 – July 2026 · Ranked against every other route with the same kind of figure and at least 4,023 in the comparison.
What sets this route apart
Where MDW to OAK differs most from similar routes by hour, weekday, month and airline, July 2023 – July 2026.
MDW to OAK struggles most at 9 PM: 49.4% of its flights scheduled then arrive on time, 20.6 points behind the 70.0% on routes of similar length at the same hour. Against all other routes the gap is 20.1 points.
Monday is the day MDW to OAK slips furthest against routes of similar length, 67.7% on time where they average 77.4%, 9.7 points lower. Against all other routes the gap is 9.6 points.
In June, MDW to OAK runs 13.9 points below routes of similar length, 58.8% on time to 72.7%. Against all other routes the gap is 13.9 points.
Southwest Airlines’ flights on MDW to OAK arrive on time 71.4% of the time, 3.8 points below the 75.2% it manages on its routes of similar length. Against all other routes the gap is 6 points.
MDW to OAK against comparable routes
July 2023 – July 2026| Measure | This route | Compared with | Them | Gap | Flights behind it |
|---|---|---|---|---|---|
| Hour: 9 PM departures | 49.4% | routes of similar length | 70.0% | −20.6 pts | 253 here, 29,588 there |
| Weekday: Monday | 67.7% | routes of similar length | 77.4% | −9.7 pts | 257 here, 176,137 there |
| Month: June | 58.8% | routes of similar length | 72.7% | −13.9 pts | 170 here, 106,502 there |
| Airline: Southwest Airlines | 71.4% | routes of similar length | 75.2% | −3.8 pts | 1,764 here, 191,191 there |
Each comparison pools the flights of other routes, with this route’s own left out. Similar length means within 15% of this route’s 1,844 miles, with at least 5 such routes. A bucket is set against the most comparable group that has enough flights: similar length, then the same origin (at least 3 routes), then all other routes. Hours, weekdays and months appear only where both sides have 120 completed flights, and airlines where both have 600. The gap must be at least 2 points and 2 standard errors, and only the largest gap each way is kept per measure. These are differences in the flights counted, not causes.
When it goes wrong
July 2023 – July 2026
47 min late
against a median of 0 min early
Percentiles over 1,785 operations; cancelled and diverted flights are counted separately.
Will your connection be tight enough?
Layovers at OAK after arriving from MDW.
| Connection time | Chance of missing | Reads as |
|---|---|---|
| 30 min | 49% | Likely to miss |
| 45 min | 28% | High risk |
| 60 min | 16% | High risk |
| 90 min | 6.4% | Some risk |
| 120 min | 3.9% | Low risk |
This is one leg of a connection. Gate changes and the next flight's own schedule matter too. And a connection can fail before delay is even the question — this route cancels 0.90% of the time and diverts 0.28% of the time, which a late arrival never shows up in.
Chance of missing is the share of 1,764 arrivals on this route that landed later than the connection time less 30 minutes to reach the next gate.
The worst tenth of arrivals on this route land at least 47 minutes late (90th-percentile gate arrival delay), over 1,785 operations.
Any other layover length: connection checker.
Best time to fly
MDW → OAK flights departing 5–9 AM arrived on time 84.8% of the time, against 49.3% for 9 PM–5 AM departures, a gap of 35.5 percentage points.
By departure window
By departure hour
- 12 AM to 5 AM: too few flights to score
- 6 AM: 90.4% on time from 149 flights
- 7 AM: 74.1% on time from 164 flights
- 8 AM: 85.0% on time from 128 flights
- 9 AM: too few flights to score
- 10 AM: 74.8% on time from 121 flights
- 11 AM to 7 PM: too few flights to score
- 8 PM: 63.1% on time from 153 flights
- 9 PM: 49.4% on time from 256 flights
- 10 PM to 11 PM: too few flights to score
Why MDW → OAK runs late
July 2023 – July 2026
crew, maintenance, boarding and fueling, all within the carrier’s control
the inbound aircraft was late, so this flight started late
airspace and airport capacity, including weather-driven flow control
weather severe enough to stop this flight specifically
screening or terminal security incidents
Share of the delay minutes US DOT attributed to each cause for MDW → OAK. Only delays of 15 minutes or more are attributed. What the five causes mean
Airlines on this route
Carriers with at least 200 flights, by the airline that operated each one.
| Carrier | Flights | On time | Cancelled | Median delay | Severe |
|---|---|---|---|---|---|
| Southwest Airlines | 1,785 | 71.4% | 0.90% | 0 min | 6.6% |
Other ways to fly Chicago to San Francisco
Airport pairs in the same two city markets, as the DOT defines them.
| Route | Flights | On time | Cancelled | Median delay | Score |
|---|---|---|---|---|---|
| ORD→SFO Chicago to San Francisco | 16,116 | 71.8% | 1.14% | -3 min | 53 |
| MDW→OAK this route Chicago to Oakland | 1,785 | 71.4% | 0.90% | 0 min | 61 |
MDW → OAK is the most reliable pairing for this journey at 71.4% on time, against 71.8% for ORD → SFO.
Flying to OAK from the Chicago area? Compare MDW, ORD for OAK, with the same test for what counts as a real difference.
Weekly and seasonal patterns
By day of week
Tuesday is historically the most reliable day and Sunday the least, a gap of 11.5 percentage points.
By month
- Jan to Feb: no data
- Mar: 74.5%
- Apr: 73.0%
- May: 69.4%
- Jun: 58.8%
- Jul: 63.5%
- Aug: 70.1%
- Sep: 76.0%
- Oct: 74.7%
- Nov: 81.6%
- Dec: 69.8%
June is historically the weakest month and November the strongest, a spread of 22.8 percentage points.
Reliability over time
July 2023 – July 2026
Over the most recent 12 months (2025-08 to 2026-07), on-time arrivals averaged 64.1% against 75.1% in the 12 months before — declining by 11.0 percentage points.
Data and methodology
Calculated by FlyerIntel from 1,785 MDW → OAK flight records from the US DOT Bureau of Transportation Statistics, covering July 2023 – July 2026. Late means 15 or more minutes past scheduled arrival; cancelled and diverted flights are left out of on-time rates.
Full methodology · Data sources · Report a problem
Related research: How Long a Layover Needs to Be · Two Airlines on One Route · Best Time of Day to Fly From Major US Airports
Analysis last recomputed