Route on-time record
SAN to MDW: most on-time flights and the best time to fly
San Diego (San Diego International Airport) to Chicago (Chicago Midway International Airport). 1,067 nonstop flights in Jun 2025 to May 2026, 77% arrived within 15 minutes and 0.9% were cancelled. The most reliable flight number was Southwest 4094 at 10:40 PM.
Flying on a specific date? We’ll adjust for the month, the weekday and the forecast.
SAN → MDW
San Diego to Chicago: 1,067 nonstop flights a year
On time (12 months)
77%
Cancelled
0.9%
avg delay 13 min
Best time to leave
After 9 PM
98% on time vs 55% 6 to 9 PM
Most reliable airline
Southwest
76% chance on time
Lowest nonstop fare seen in the next two months: $196 (Southwest 674 on 2026-11-03). 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 4094
10:40 PM → 4:35 AM3h 55m nonstop
Local times, typical schedule. Last flown 2026-05-31. Same departure also flew as Southwest 990; its record covers all of them.
93%
chance on time
- On time (history)
- 98%
- Cancelled
- 2.3%
- Avg arrival delay
- 2 min
- Arrived on time 98% of the time (85 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (After 9 PM: 98% on time; 6 to 9 PM: 55%).
- Departs outside SAN's trouble window (6 AM to noon, when 66% of its 164 ground stops and delay programs started).
Moderate track record · 85 flights
Find Southwest 4094 fares Opens this date on Aviasales#2 · Southwest 2709
6:45 AM → 12:45 PM4h 00m nonstop
Local times, typical schedule. Last flown 2026-04-06.
88%
chance on time
- On time (history)
- 92%
- Cancelled
- 3.6%
- Avg arrival delay
- 9 min
- Arrived on time 92% of the time (26 flights, Jun 2025 to May 2026).
- Departs inside SAN's trouble window: 66% of its 164 ground stops and delay programs started between 6 AM and noon.
- 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 2709 fares Opens this date on Aviasales#3 · Southwest 3292
7:10 AM → 1:05 PM3h 55m nonstop
Local times, typical schedule. Last flown 2026-05-31.
82%
chance on time
- On time (history)
- 83%
- Cancelled
- 0.0%
- Avg arrival delay
- 9 min
- Arrived on time 83% of the time (54 flights, Jun 2025 to May 2026).
- Never cancelled in 54 scheduled flights.
- Departs inside SAN's trouble window: 66% of its 164 ground stops and delay programs started between 6 AM and noon.
- Short track record (54 flights), so its score leans on the airline's record at this hour.
Limited track record · 54 flights
Find Southwest 3292 fares Opens this date on Aviasales#4 · Southwest 3910
12:10 PM → 6:05 PM3h 55m nonstop
Local times, typical schedule. Last flown 2026-04-06.
72%
chance on time
- On time (history)
- 70%
- Cancelled
- 0.0%
- Avg arrival delay
- 14 min
- Arrived on time 70% of the time (20 flights, Jun 2025 to May 2026).
- Departs outside SAN's trouble window (6 AM to noon, when 66% of its 164 ground stops and delay programs started).
- Short track record (20 flights), so its score leans on the airline's record at this hour.
Limited track record · 20 flights
Find Southwest 3910 fares Opens this date on Aviasales#5 · Southwest 4025
11:55 AM → 5:55 PM4h 00m nonstop
Local times, typical schedule. Last flown 2026-05-31.
71%
chance on time
- On time (history)
- 70%
- Cancelled
- 0.0%
- Avg arrival delay
- 10 min
- Arrived on time 70% of the time (53 flights, Jun 2025 to May 2026).
- Never cancelled in 55 scheduled flights.
- Departs inside SAN's trouble window: 66% of its 164 ground stops and delay programs started between 6 AM and noon.
- Short track record (53 flights), so its score leans on the airline's record at this hour.
Limited track record · 53 flights
Find Southwest 4025 fares Opens this date on Aviasales#6 · Southwest 4363
4:45 PM → 10:35 PM3h 50m nonstop
Local times, typical schedule. Last flown 2026-04-06.
70%
chance on time
- On time (history)
- 64%
- Cancelled
- 0.0%
- Avg arrival delay
- 28 min
- Arrived on time 64% of the time (22 flights, Jun 2025 to May 2026).
- Departs outside SAN's trouble window (6 AM to noon, when 66% of its 164 ground stops and delay programs started).
- 51% of its delay minutes came from the plane arriving late from an earlier flight.
- Short track record (22 flights), so its score leans on the airline's record at this hour.
Limited track record · 22 flights
Find Southwest 4363 fares Opens this date on Aviasales#7 · Southwest 2712
3:45 PM → 9:35 PM3h 50m nonstop
Local times, typical schedule. Last flown 2026-05-29.
54%
chance on time
- On time (history)
- 27%
- Cancelled
- 4.3%
- Avg arrival delay
- 52 min
- Arrived on time 27% of the time (22 flights, Jun 2025 to May 2026).
- Departs outside SAN's trouble window (6 AM to noon, when 66% of its 164 ground stops and delay programs started).
- 56% of its delay minutes came from the plane arriving late from an earlier flight.
- Short track record (22 flights), so its score leans on the airline's record at this hour.
Limited track record · 22 flights
Find Southwest 2712 fares Opens this date on Aviasales
Airlines on this route
Season-adjusted chance of operating and arriving on time.
- Southwest Airlines76%
1,067 flights · 77% on time as flown · 0.9% cancel
On time by departure time
All airlines, scheduled local departure, Jun 2025 to May 2026.
- Before 9 AM89%
372 flights · avg delay 7 min
- 9 AM to noon78%
211 flights · avg delay 12 min
- Noon to 3 PM64%
134 flights · avg delay 18 min
- 3 to 6 PM62%
138 flights · avg delay 23 min
- 6 to 9 PM55%
124 flights · avg delay 27 min
- After 9 PM98%
88 flights · avg delay 2 min
Best day: Saturday (85%). Worst: Sunday (73%).
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 aircraft50%
- Airline (crew, maintenance, boarding)33%
- Air traffic control and airport volume16%
- Security1%
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
SAN to MDW questions
- What time of day is best to fly SAN to MDW?
- After 9 PM: 98% of flights arrived on time, against 55% for departures 6 to 9 PM.
- Which airline is most on time from SAN to MDW?
- Southwest, with a season-adjusted 76% chance of operating and arriving on time over 1,067 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 SAN to MDW?
- June (67% on time); the best was November (84%), 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 SAN
- MDW to SAN (return)
- SAN to SFO 68%
- SAN to LAS 76%
- SAN to DEN 79%
- SAN to PHX 76%
- SAN to SMF 77%
- SAN to SJC 78%
- SAN to SEA 81%
- SAN to ORD 78%
- SAN to DFW 77%
- SAN to OAK 75%
- SAN to SLC 84%
- SAN to AUS 74%
Live status: FAA delays and ground stops