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Route on-time record

RSW to MDW: most on-time flights and the best time to fly

Fort Myers (Southwest Florida International Airport) to Chicago (Chicago Midway International Airport). 1,161 nonstop flights in Jun 2025 to May 2026, 76% arrived within 15 minutes and 1.3% were cancelled. The most reliable flight number was Southwest 164 at 7:00 AM.

Flying on a specific date? We’ll adjust for the month, the weekday and the forecast.

RSW → MDW

Fort Myers to Chicago: 1,161 nonstop flights a year

On time (12 months)

76%

Cancelled

1.3%

avg delay 15 min

Best time to leave

Before 9 AM

95% on time vs 53% 6 to 9 PM

Most reliable airline

Southwest

75% chance on time

Check RSW to MDW fares

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. #1 · Southwest 164

    7:00 AM → 8:55 AM2h 55m nonstop

    Local times, typical schedule. Last flown 2026-05-31.

    88%

    chance on time

    On time (history)
    93%
    Cancelled
    0.0%
    Avg arrival delay
    4 min
    • Arrived on time 93% of the time (55 flights, Jun 2025 to May 2026).
    • Never cancelled in 55 scheduled flights.
    • Leaves in this route's most on-time window (Before 9 AM: 95% on time; 6 to 9 PM: 53%).
    • 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 · 55 flights

    Find Southwest 164 fares Opens this date on Aviasales

  2. #2 · Southwest 4331

    7:15 AM → 9:15 AM3h 00m nonstop

    Local times, typical schedule. Last flown 2026-04-06.

    87%

    chance on time

    On time (history)
    97%
    Cancelled
    9.1%
    Avg arrival delay
    1 min
    • Arrived on time 97% of the time (30 flights, Jun 2025 to May 2026).
    • Cancelled 9.1% of the time (3 of 33).
    • Leaves in this route's most on-time window (Before 9 AM: 95% on time; 6 to 9 PM: 53%).
    • 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 · 30 flights

    Find Southwest 4331 fares Opens this date on Aviasales

  3. #3 · Southwest 1160

    11:55 AM → 2:00 PM3h 05m nonstop

    Local times, typical schedule. Last flown 2026-05-27.

    76%

    chance on time

    On time (history)
    81%
    Cancelled
    0.0%
    Avg arrival delay
    7 min
    • Arrived on time 81% of the time (16 flights, Jun 2025 to May 2026).
    • Short track record (16 flights), so its score leans on the airline's record at this hour.

    Limited track record · 16 flights

    Find Southwest 1160 fares Opens this date on Aviasales

  4. #4 · Southwest 3997

    1:05 PM → 3:20 PM3h 15m nonstop

    Local times, typical schedule. Last flown 2026-04-06.

    73%

    chance on time

    On time (history)
    65%
    Cancelled
    3.0%
    Avg arrival delay
    21 min
    • Arrived on time 65% of the time (31 flights, Jun 2025 to May 2026).
    • Cancelled 3.0% of the time (1 of 33).
    • 61% of its delay minutes came from the plane arriving late from an earlier flight.
    • Short track record (31 flights), so its score leans on the airline's record at this hour.

    Limited track record · 31 flights

    Find Southwest 3997 fares Opens this date on Aviasales

  5. #5 · Southwest 2752

    10:15 AM → 12:10 PM2h 55m nonstop

    Local times, typical schedule. Last flown 2026-05-31. Same departure also flew as Southwest 4332; its record covers all of them.

    72%

    chance on time

    On time (history)
    68%
    Cancelled
    2.8%
    Avg arrival delay
    16 min
    • Arrived on time 68% of the time (69 flights, Jun 2025 to May 2026).
    • Lands inside MDW's trouble window: 50% of its 30 ground stops and delay programs started between 7 AM and 1 PM.

    Moderate track record · 69 flights

    Find Southwest 2752 fares Opens this date on Aviasales

  6. #6 · Southwest 4708

    3:40 PM → 5:45 PM3h 05m nonstop

    Local times, typical schedule. Last flown 2026-04-01.

    69%

    chance on time

    On time (history)
    57%
    Cancelled
    0.0%
    Avg arrival delay
    20 min
    • Arrived on time 57% of the time (7 flights, Jun 2025 to May 2026).
    • 55% of its delay minutes came from the plane arriving late from an earlier flight.
    • Short track record (7 flights), so its score leans on the airline's record at this hour.

    Limited track record · 7 flights

    Find Southwest 4708 fares Opens this date on Aviasales

  7. #7 · Southwest 4333

    9:15 PM → 11:15 PM3h 00m nonstop

    Local times, typical schedule. Last flown 2026-04-05.

    65%

    chance on time

    On time (history)
    37%
    Cancelled
    0.0%
    Avg arrival delay
    44 min
    • Arrived on time 37% of the time (19 flights, Jun 2025 to May 2026).
    • 91% of its delay minutes came from the plane arriving late from an earlier flight.
    • Short track record (19 flights), so its score leans on the airline's record at this hour.

    Limited track record · 19 flights

    Find Southwest 4333 fares Opens this date on Aviasales

  8. #8 · Southwest 4043

    8:25 PM → 10:20 PM3h 00m nonstop

    Local times, typical schedule. Last flown 2026-05-31.

    64%

    chance on time

    On time (history)
    58%
    Cancelled
    0.0%
    Avg arrival delay
    26 min
    • Arrived on time 58% of the time (55 flights, Jun 2025 to May 2026).
    • Never cancelled in 55 scheduled flights.
    • Leaves in this route's least on-time window (6 to 9 PM: 53% on time; Before 9 AM: 95%).
    • 52% of its delay minutes came from the plane arriving late from an earlier flight.

    Limited track record · 55 flights

    Find Southwest 4043 fares Opens this date on Aviasales

  9. #9 · Southwest 4113

    7:55 PM → 9:55 PM3h 00m nonstop

    Local times, typical schedule. Last flown 2026-04-06.

    64%

    chance on time

    On time (history)
    58%
    Cancelled
    7.7%
    Avg arrival delay
    27 min
    • Arrived on time 58% of the time (12 flights, Jun 2025 to May 2026).
    • Leaves in this route's least on-time window (6 to 9 PM: 53% on time; Before 9 AM: 95%).
    • Short track record (12 flights), so its score leans on the airline's record at this hour.

    Limited track record · 12 flights

    Find Southwest 4113 fares Opens this date on Aviasales

  10. #10 · Southwest 4006

    5:10 PM → 7:20 PM3h 10m nonstop

    Local times, typical schedule. Last flown 2026-04-06.

    62%

    chance on time

    On time (history)
    45%
    Cancelled
    0.0%
    Avg arrival delay
    82 min
    • Arrived on time 45% of the time (20 flights, Jun 2025 to May 2026).
    • 66% of its delay minutes came from the plane arriving late from an earlier flight.
    • Short track record (20 flights), so its score leans on the airline's record at this hour.

    Limited track record · 20 flights

    Find Southwest 4006 fares Opens this date on Aviasales

Airlines on this route

Season-adjusted chance of operating and arriving on time.

  • Southwest Airlines75%

    1,161 flights · 76% on time as flown · 1.3% cancel

On time by departure time

All airlines, scheduled local departure, Jun 2025 to May 2026.

  • Before 9 AM95%

    338 flights · avg delay 4 min

  • 9 AM to noon78%

    228 flights · avg delay 12 min

  • Noon to 3 PM75%

    164 flights · avg delay 13 min

  • 3 to 6 PM65%

    219 flights · avg delay 24 min

  • 6 to 9 PM53%

    170 flights · avg delay 29 min

  • After 9 PM73%

    42 flights · avg delay 20 min

Best day: Thursday (80%). Worst: Sunday (74%).

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.

J
78
F
80
M
71
A
77
M
72
J
79
J
70
A
76
S
86
O
85
N
84
D
73

What delays this route

  • Late-arriving aircraft59%
  • Airline (crew, maintenance, boarding)20%
  • Air traffic control and airport volume16%
  • Severe weather5%

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

RSW to MDW questions

What time of day is best to fly RSW to MDW?
Before 9 AM: 95% of flights arrived on time, against 53% for departures 6 to 9 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 RSW to MDW?
Southwest, with a season-adjusted 75% chance of operating and arriving on time over 1,161 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 RSW to MDW?
July (70% on time); the best was September (86%), 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 RSW

Live status: FAA delays and ground stops