Route profile
OAK→MDW
Flight reliability, delays and best times to fly from Oakland to Chicago, 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 93% of comparable major US routes (4,598 compared)
Calculated from 1,776 flights. How this is calculated
OAK → MDW arrives on time 83.1% of the time; the return trip, MDW → OAK, arrives on time 71.4% of the time, an 11.7-point gap between the two directions of the same city pair.
OAK → MDW spends 18.0 minutes on the ground on a 1,844-mile trip: 13.3 minutes from pushback to wheels-up at OAK and 4.6 minutes from touchdown to gate at MDW.
Source: US DOT Bureau of Transportation Statistics · Data covering July 2023 – July 2026
What stands out
This route stays close to typical even on its worst days, a smaller gap than 91% of 4,598 comparable routes.
A typical arrival is 5 min early, and the worst tenth are only 31 minutes worse than that.
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 4,598 in the comparison.
What sets this route apart
Where OAK to MDW differs most from similar routes by hour, weekday, month and airline, July 2023 – July 2026.
OAK to MDW struggles most at 6 PM: 59.4% of its flights scheduled then arrive on time, 10.7 points behind the 70.1% on routes of similar length at the same hour. Against all other routes the gap is 9.2 points.
OAK to MDW is at its best against routes of similar length for flights scheduled at 11 AM: 85.1% arrive on time, 7.4 points ahead of the 77.7% those routes manage at that hour.
OAK to MDW holds up on Sundays better than routes of similar length do: 83.1% on time to their 75.5%, a 7.6 points lead. Against all other routes the gap is 8.3 points.
May is kinder to OAK to MDW than to routes of similar length: 89.1% on time against 76.0%, 13.1 points better. Against all other routes the gap is 13.9 points.
Southwest Airlines does better on OAK to MDW than on its routes of similar length: 83.1% on time here, 75.1% there, 8 points apart. Against all other routes the gap is 5.7 points.
OAK to MDW against comparable routes
July 2023 – July 2026| Measure | This route | Compared with | Them | Gap | Flights behind it |
|---|---|---|---|---|---|
| Hour: 6 PM departures | 59.4% | routes of similar length | 70.1% | −10.7 pts | 202 here, 65,402 there |
| Hour: 11 AM departures | 85.1% | routes of similar length | 77.7% | +7.4 pts | 154 here, 69,805 there |
| Weekday: Sunday | 83.1% | routes of similar length | 75.5% | +7.6 pts | 242 here, 174,882 there |
| Month: May | 89.1% | routes of similar length | 76.0% | +13.1 pts | 137 here, 102,832 there |
| Airline: Southwest Airlines | 83.1% | routes of similar length | 75.1% | +8.0 pts | 1,759 here, 191,196 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
26 min late
against a median of 5 min early
Percentiles over 1,776 operations; cancelled and diverted flights are counted separately.
Will your connection be tight enough?
Layovers at MDW after arriving from OAK.
| Connection time | Chance of missing | Reads as |
|---|---|---|
| 30 min | 37% | Likely to miss |
| 45 min | 16% | High risk |
| 60 min | 8.2% | Some risk |
| 90 min | 3.1% | Low risk |
| 120 min | 1.4% | 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 0.39% of the time and diverts 0.56% of the time, which a late arrival never shows up in.
Chance of missing is the share of 1,759 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 26 minutes late (90th-percentile gate arrival delay), over 1,776 operations.
Any other layover length: connection checker.
Best time to fly
OAK → MDW flights departing 5–9 AM arrived on time 92.4% of the time, against 62.3% for 6–9 PM departures, a gap of 30.1 percentage points.
By departure window
By departure hour
- 12 AM to 4 AM: too few flights to score
- 5 AM: 90.8% on time from 625 flights
- 6 AM: 96.4% on time from 225 flights
- 7 AM to 10 AM: too few flights to score
- 11 AM: 85.1% on time from 156 flights
- 12 PM to 5 PM: too few flights to score
- 6 PM: 59.4% on time from 206 flights
- 7 PM to 10 PM: too few flights to score
- 11 PM: 78.5% on time from 149 flights
Departure windows with fewer than 120 flights are not scored.
Why OAK → MDW runs late
July 2023 – July 2026
the inbound aircraft was late, so this flight started late
crew, maintenance, boarding and fueling, all within the carrier’s control
airspace and airport capacity, including weather-driven flow control
screening or terminal security incidents
Share of the delay minutes US DOT attributed to each cause for OAK → MDW. Only delays of 15 minutes or more are attributed.
Late-arriving aircraft is the largest cause on OAK → MDW, at 43.3%: flights here mostly leave late because the plane came in late, and the day shows it: 5–9 AM departures arrived on time 92.4% of the time and 6–9 PM departures 62.3%.
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 | 1,776 | 83.1% | 0.39% | -5 min | 3.2% |
Other ways to fly San Francisco to Chicago
Airport pairs in the same two city markets, as the DOT defines them.
| Route | Flights | On time | Cancelled | Median delay | Score |
|---|---|---|---|---|---|
| SFO→ORD San Francisco to Chicago | 16,120 | 78.7% | 1.12% | -7 min | 66 |
| OAK→MDW this route Oakland to Chicago | 1,776 | 83.1% | 0.39% | -5 min | 84 |
OAK → MDW is the most reliable pairing for this journey at 83.1% on time, against 78.7% for SFO → ORD.
Flying to MDW from the San Francisco area? Compare OAK, SFO, SJC for MDW, with the same test for what counts as a real difference.
Weekly and seasonal patterns
By day of week
Saturday is historically the most reliable day and Monday the least, a gap of 10.2 percentage points.
By month
- Jan to Feb: no data
- Mar: 84.4%
- Apr: 89.7%
- May: 89.1%
- Jun: 73.5%
- Jul: 76.7%
- Aug: 80.1%
- Sep: 80.3%
- Oct: 91.7%
- Nov: 85.8%
- Dec: 82.0%
June is historically the weakest month and October the strongest, a spread of 18.2 percentage points.
Reliability over time
July 2023 – July 2026
Over the most recent 12 months (2025-08 to 2026-07), on-time arrivals averaged 84.6% against 87.9% in the 12 months before — declining by 3.3 percentage points.
Data and methodology
Calculated by FlyerIntel from 1,776 OAK → MDW 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