Route on-time record
MDW to OAK: most on-time flights and the best time to fly
Chicago (Chicago Midway International Airport) to Oakland (Oakland San Francisco Bay Airport). 460 nonstop flights in Jun 2025 to May 2026, 65% arrived within 15 minutes and 1.3% were cancelled. The most reliable flight number was Southwest 1743 at 10:05 AM.
Flying on a specific date? We’ll adjust for the month, the weekday and the forecast.
MDW → OAK
Chicago to Oakland: 460 nonstop flights a year
On time (12 months)
65%
Cancelled
1.3%
avg delay 20 min
Best time to leave
9 AM to noon
79% on time vs 48% after 9 PM
Most reliable airline
Southwest
64% 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 1743
10:05 AM → 12:40 PM4h 35m nonstop
Local times, typical schedule. Last flown 2026-05-31. Same departure also flew as Southwest 192, 2484; its record covers all of them.
70%
chance on time
- On time (history)
- 72%
- Cancelled
- 1.9%
- Avg arrival delay
- 14 min
- Arrived on time 72% of the time (101 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (9 AM to noon: 79% on time; After 9 PM: 48%).
- Departs inside MDW's trouble window: 50% of its 30 ground stops and delay programs started between 7 AM and 1 PM.
Moderate track record · 101 flights
Find Southwest 1743 fares Opens this date on Aviasales#2 · Southwest 1748
9:50 PM → 12:25 AM4h 35m nonstop
Local times, typical schedule. Last flown 2026-05-29.
54%
chance on time
- On time (history)
- 48%
- Cancelled
- 0.0%
- Avg arrival delay
- 36 min
- Arrived on time 48% of the time (23 flights, Jun 2025 to May 2026).
- Leaves in this route's least on-time window (After 9 PM: 48% on time; 9 AM to noon: 79%).
- Departs outside MDW's trouble window (7 AM to 1 PM, when 50% of its 30 ground stops and delay programs started).
- 53% of its delay minutes came from the plane arriving late from an earlier flight.
Limited track record · 23 flights
Find Southwest 1748 fares Opens this date on Aviasales#3 · Southwest 1394
9:30 PM → 12:10 AM4h 40m nonstop
Local times, typical schedule. Last flown 2026-04-06.
52%
chance on time
- On time (history)
- 44%
- Cancelled
- 7.4%
- Avg arrival delay
- 40 min
- Arrived on time 44% of the time (25 flights, Jun 2025 to May 2026).
- Leaves in this route's least on-time window (After 9 PM: 48% on time; 9 AM to noon: 79%).
- Departs outside MDW's trouble window (7 AM to 1 PM, when 50% of its 30 ground stops and delay programs started).
- 66% of its delay minutes came from the plane arriving late from an earlier flight.
Limited track record · 25 flights
Find Southwest 1394 fares Opens this date on Aviasales
Airlines on this route
Season-adjusted chance of operating and arriving on time.
- Southwest Airlines64%
460 flights · 65% on time as flown · 1.3% cancel
On time by departure time
All airlines, scheduled local departure, Jun 2025 to May 2026.
- Before 9 AM65%
119 flights · avg delay 18 min
- 9 AM to noon79%
109 flights · avg delay 11 min
- Noon to 3 PM67%
30 flights · avg delay 11 min
- 3 to 6 PM65%
100 flights · avg delay 20 min
- 6 to 9 PM53%
36 flights · avg delay 32 min
- After 9 PM48%
66 flights · avg delay 35 min
Best day: Tuesday (78%). Worst: Sunday (68%).
Smarter routing
Nearby airports that run more on time
MDW → SJC 70% chance on time
Chicago Midway International Airport to Norman Y. Mineta San Jose International Airport · 545 flights a year · 29 mi from your airports · yours: 64%
ORD → SFO 69% chance on time
Chicago O'Hare International Airport to San Francisco International Airport · 5,607 flights a year · 26 mi from your airports · yours: 64%
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
- Late-arriving aircraft42%
- Airline (crew, maintenance, boarding)37%
- Air traffic control and airport volume19%
- Severe weather1%
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
MDW to OAK questions
- What time of day is best to fly MDW to OAK?
- 9 AM to noon: 79% of flights arrived on time, against 48% for departures after 9 PM.
- Which airline is most on time from MDW to OAK?
- Southwest, with a season-adjusted 64% chance of operating and arriving on time over 460 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 MDW to OAK?
- July (61% on time); the best was November (82%), 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 MDW
- OAK to MDW (return)
- MDW to ATL 80%
- MDW to PHX 76%
- MDW to MCO 77%
- MDW to MSP 78%
- MDW to LAS 77%
- MDW to DEN 73%
- MDW to LGA 69%
- MDW to DAL 77%
- MDW to DCA 69%
- MDW to MCI 79%
- MDW to BNA 80%
- MDW to BWI 79%
Live status: FAA delays and ground stops