Route on-time record
OAK to MDW: most on-time flights and the best time to fly
Oakland (Oakland San Francisco Bay Airport) to Chicago (Chicago Midway International Airport). 459 nonstop flights in Jun 2025 to May 2026, 88% arrived within 15 minutes and 0.2% were cancelled. The most reliable flight number was Southwest 3551 at 5:55 AM.
Flying on a specific date? We’ll adjust for the month, the weekday and the forecast.
OAK → MDW
Oakland to Chicago: 459 nonstop flights a year
On time (12 months)
88%
Cancelled
0.2%
avg delay 5 min
Best time to leave
Before 9 AM
91% on time vs 84% noon to 3 PM
Most reliable airline
Southwest
88% chance on time
Fares open on our travel partner (Aviasales). Pick the flight number you chose here.
Most reliable nonstop flights
Ranked by the chance the flight operates and arrives within 15 minutes of schedule, from Jun 2025 to May 2026 records.
#1 · Southwest 3551
5:55 AM → 12:00 PM4h 05m nonstop
Local times, typical schedule. Last flown 2026-05-29.
90%
chance on time
- On time (history)
- 90%
- Cancelled
- 0.0%
- Avg arrival delay
- 5 min
- Arrived on time 90% of the time (39 flights, Jun 2025 to May 2026).
- Never cancelled in 39 scheduled flights.
- Leaves in this route's most on-time window (Before 9 AM: 91% on time; Noon to 3 PM: 84%).
- Lands inside MDW's trouble window: 50% of its 30 ground stops and delay programs started between 7 AM and 1 PM.
Limited track record · 39 flights
Find Southwest 3551 fares Opens this date on Aviasales#2 · Southwest 1150
5:45 AM → 11:45 AM4h 00m nonstop
Local times, typical schedule. Last flown 2026-04-06.
87%
chance on time
- On time (history)
- 85%
- Cancelled
- 3.6%
- Avg arrival delay
- 7 min
- Arrived on time 85% of the time (26 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (Before 9 AM: 91% on time; Noon to 3 PM: 84%).
- Lands inside MDW's trouble window: 50% of its 30 ground stops and delay programs started between 7 AM and 1 PM.
- Short track record (26 flights), so its score leans on the airline's record at this hour.
Limited track record · 26 flights
Find Southwest 1150 fares Opens this date on Aviasales#3 · Southwest 3552
11:55 PM → 6:00 AM4h 05m nonstop
Local times, typical schedule. Last flown 2026-05-31. Same departure also flew as Southwest 4069; its record covers all of them.
87%
chance on time
- On time (history)
- 86%
- Cancelled
- 0.0%
- Avg arrival delay
- 6 min
- Arrived on time 86% of the time (87 flights, Jun 2025 to May 2026).
- Never cancelled in 87 scheduled flights.
Moderate track record · 87 flights
Find Southwest 3552 fares Opens this date on Aviasales
Airlines on this route
Season-adjusted chance of operating and arriving on time.
- Southwest Airlines88%
459 flights · 88% on time as flown · 0.2% cancel
On time by departure time
All airlines, scheduled local departure, Jun 2025 to May 2026.
- Before 9 AM91%
241 flights · avg delay 4 min
- 9 AM to noon85%
88 flights · avg delay 6 min
- Noon to 3 PM84%
33 flights · avg delay 11 min
- After 9 PM86%
88 flights · avg delay 6 min
Best day: Saturday (86%). Worst: Monday (76%).
Smarter routing
Nearby airports that run more on time
SJC → ORD 91% chance on time
Norman Y. Mineta San Jose International Airport to Chicago O'Hare International Airport · 301 flights a year · 44 mi from your airports · yours: 88%
On time by month
All airlines, Jun 2023 to May 2026. Several years per month, so one stormy season doesn't define a month. Travel-month estimates use this seasonal pattern.
What delays this route
- Airline (crew, maintenance, boarding)42%
- Late-arriving aircraft31%
- Air traffic control and airport volume27%
Share of delay minutes by the cause airlines report to the US DOT.
Historical odds, not a guarantee. Built from the US DOT Bureau of Transportation Statistics on-time reports (Jun 2025 to May 2026), FAA ground stop and delay program advisories, and 20 years of airport weather observations. Covers US airlines that report to the DOT; schedules are flights operated recently, so confirm times when you book. ATIS Alerts is not affiliated with any airline. Fares are what Aviasales travelers saw in recent searches (USD, one way, 1 adult), not live quotes; the partner site shows the current price. Fare links go to our travel partner and may earn us a commission at no cost to you. Affiliate disclosure
OAK to MDW questions
- What time of day is best to fly OAK to MDW?
- Before 9 AM: 91% of flights arrived on time, against 84% for departures noon to 3 PM. Later flights inherit delays from earlier ones, so the first departures of the day usually run best.
- Which airline is most on time from OAK to MDW?
- Southwest, with a season-adjusted 88% chance of operating and arriving on time over 459 flights. The adjustment compares each airline with what the route did in the months it flew, so a carrier that skipped a stormy month gets no free credit.
- What is the worst month for delays on OAK to MDW?
- June (70% on time); the best was February (92%), averaged over Jun 2023 to May 2026.
- Is this a prediction for my flight?
- No. These are historical odds from the US DOT on-time reports, FAA advisories and airport weather records. Check your flight status and the FAA delay board on the day you fly.
More routes from OAK
- MDW to OAK (return)
- OAK to LAS 80%
- OAK to SAN 69%
- OAK to BUR 82%
- OAK to SNA 86%
- OAK to LAX 81%
- OAK to PHX 78%
- OAK to SEA 77%
- OAK to SLC 89%
- OAK to LGB 87%
- OAK to DEN 73%
- OAK to ONT 83%
- OAK to PDX 81%
Live status: FAA delays and ground stops