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Route on-time record

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

Portland (Portland International Airport) to Chicago (Chicago Midway International Airport). 686 nonstop flights in Jun 2025 to May 2026, 89% arrived within 15 minutes and 0.7% were cancelled. The most reliable flight number was Southwest 1162 at 5:10 AM.

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

PDX → MDW

Portland to Chicago: 686 nonstop flights a year

On time (12 months)

89%

Cancelled

0.7%

avg delay 6 min

Best time to leave

After 9 PM

94% on time vs 68% noon to 3 PM

Most reliable airline

Southwest

88% chance on time

Check PDX to MDW fares

Lowest nonstop fare seen in the next two months: $255 (Southwest 2737 on 2026-10-24). 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 1162

    5:10 AM → 11:05 AM3h 55m nonstop

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

    93%

    chance on time

    On time (history)
    96%
    Cancelled
    0.0%
    Avg arrival delay
    4 min
    • Arrived on time 96% of the time (54 flights, Jun 2025 to May 2026).
    • Never cancelled in 54 scheduled flights.
    • 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 (54 flights), so its score leans on the airline's record at this hour.

    Limited track record · 54 flights

    Find Southwest 1162 fares Opens this date on Aviasales

  2. #2 · Southwest 3708

    11:55 PM → 5:50 AM3h 55m nonstop

    Local times, typical schedule. Last flown 2026-05-31. Same departure also flew as Southwest 4161; its record covers all of them.

    91%

    chance on time

    On time (history)
    94%
    Cancelled
    2.3%
    Avg arrival delay
    3 min
    • Arrived on time 94% of the time (84 flights, Jun 2025 to May 2026).
    • Leaves in this route's most on-time window (After 9 PM: 94% on time; Noon to 3 PM: 68%).

    Moderate track record · 84 flights

    Find Southwest 3708 fares Opens this date on Aviasales

  3. #3 · Southwest 280

    5:20 AM → 11:15 AM3h 55m nonstop

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

    90%

    chance on time

    On time (history)
    94%
    Cancelled
    6.1%
    Avg arrival delay
    4 min
    • Arrived on time 94% of the time (31 flights, Jun 2025 to May 2026).
    • Cancelled 6.1% of the time (2 of 33).
    • 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 (31 flights), so its score leans on the airline's record at this hour.

    Limited track record · 31 flights

    Find Southwest 280 fares Opens this date on Aviasales

Airlines on this route

Season-adjusted chance of operating and arriving on time.

  • Southwest Airlines88%

    686 flights · 89% on time as flown · 0.7% cancel

On time by departure time

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

  • Before 9 AM94%

    426 flights · avg delay 4 min

  • 9 AM to noon90%

    40 flights · avg delay 7 min

  • Noon to 3 PM68%

    131 flights · avg delay 13 min

  • After 9 PM94%

    89 flights · avg delay 3 min

Best day: Saturday (92%). Worst: Sunday (84%).

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
88
F
93
M
92
A
96
M
95
J
80
J
86
A
90
S
89
O
89
N
95
D
85

What delays this route

  • Late-arriving aircraft43%
  • Airline (crew, maintenance, boarding)33%
  • Air traffic control and airport volume23%
  • 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

PDX to MDW questions

What time of day is best to fly PDX to MDW?
After 9 PM: 94% of flights arrived on time, against 68% for departures noon to 3 PM.
Which airline is most on time from PDX to MDW?
Southwest, with a season-adjusted 88% chance of operating and arriving on time over 686 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 PDX to MDW?
June (80% on time); the best was April (96%), 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 PDX

Live status: FAA delays and ground stops