Route on-time record

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

Houston (William P. Hobby Airport) to Chicago (Chicago Midway International Airport). 1,844 nonstop flights in Jun 2025 to May 2026, 74% arrived within 15 minutes and 1.2% were cancelled. The most reliable flight number was Southwest 3755 at 5:10 AM.

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

HOU → MDW

Houston to Chicago: 1,844 nonstop flights a year

On time (12 months)

74%

Cancelled

1.2%

avg delay 14 min

Best time to leave

Before 9 AM

88% on time vs 64% 3 to 6 PM

Most reliable airline

Southwest

74% chance on time

Check HOU to MDW fares

Lowest nonstop fare seen in the next two months: $250 (Southwest 4638 on 2026-10-28). 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 3755
5:10 AM → 7:35 AM2h 25m nonstop
Local times, typical schedule. Last flown 2026-05-29.
87%
chance on time
On time (history)
95%
Cancelled
0.0%
Avg arrival delay
2 min
- Arrived on time 95% of the time (22 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (Before 9 AM: 88% on time; 3 to 6 PM: 64%).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
- 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 · 22 flights
Find Southwest 3755 fares Opens this date on Aviasales
#2 · Southwest 3907
5:00 AM → 7:25 AM2h 25m nonstop
Local times, typical schedule. Last flown 2026-05-31. Same departure also flew as Southwest 3490; its record covers all of them.
84%
chance on time
On time (history)
86%
Cancelled
4.3%
Avg arrival delay
5 min
- Arrived on time 86% of the time (21 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (Before 9 AM: 88% on time; 3 to 6 PM: 64%).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
- 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 · 21 flights
Find Southwest 3907 fares Opens this date on Aviasales
#3 · Southwest 4520
7:10 AM → 9:35 AM2h 25m nonstop
Local times, typical schedule. Last flown 2026-05-27.
83%
chance on time
On time (history)
88%
Cancelled
0.0%
Avg arrival delay
7 min
- Arrived on time 88% of the time (16 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (Before 9 AM: 88% on time; 3 to 6 PM: 64%).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
- 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 · 16 flights
Find Southwest 4520 fares Opens this date on Aviasales
#4 · Southwest 2968
6:15 AM → 8:35 AM2h 20m nonstop
Local times, typical schedule. Last flown 2026-04-05.
82%
chance on time
On time (history)
77%
Cancelled
0.0%
Avg arrival delay
8 min
- Arrived on time 77% of the time (13 flights, Jun 2025 to May 2026).
- Leaves in this route's most on-time window (Before 9 AM: 88% on time; 3 to 6 PM: 64%).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
- 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 · 13 flights
Find Southwest 2968 fares Opens this date on Aviasales
#5 · Southwest 2002
12:55 PM → 3:25 PM2h 25m nonstop
Local times, typical schedule. Last flown 2026-05-31.
80%
chance on time
On time (history)
85%
Cancelled
0.0%
Avg arrival delay
9 min
- Arrived on time 85% of the time (55 flights, Jun 2025 to May 2026).
- Never cancelled in 55 scheduled flights.
- Departs inside HOU's trouble window: 80% of its 40 ground stops and delay programs started between noon and 6 PM.
- Short track record (55 flights), so its score leans on the airline's record at this hour.
Limited track record · 55 flights
Find Southwest 2002 fares Opens this date on Aviasales
#6 · Southwest 2649
8:10 AM → 10:35 AM2h 25m nonstop
Local times, typical schedule. Last flown 2026-04-06.
78%
chance on time
On time (history)
74%
Cancelled
3.0%
Avg arrival delay
12 min
- Arrived on time 74% of the time (31 flights, Jun 2025 to May 2026).
- Cancelled 3.0% of the time (1 of 33).
- Leaves in this route's most on-time window (Before 9 AM: 88% on time; 3 to 6 PM: 64%).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
Limited track record · 31 flights
Find Southwest 2649 fares Opens this date on Aviasales
#7 · Southwest 2963
8:00 AM → 10:25 AM2h 25m nonstop
Local times, typical schedule. Last flown 2026-05-31.
77%
chance on time
On time (history)
75%
Cancelled
0.0%
Avg arrival delay
9 min
- Arrived on time 75% of the time (53 flights, Jun 2025 to May 2026).
- Never cancelled in 55 scheduled flights.
- Leaves in this route's most on-time window (Before 9 AM: 88% on time; 3 to 6 PM: 64%).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
Limited track record · 53 flights
Find Southwest 2963 fares Opens this date on Aviasales
#8 · Southwest 4642
12:25 PM → 2:45 PM2h 20m nonstop
Local times, typical schedule. Last flown 2026-04-06.
69%
chance on time
On time (history)
56%
Cancelled
0.0%
Avg arrival delay
19 min
- Arrived on time 56% of the time (18 flights, Jun 2025 to May 2026).
- Departs inside HOU's trouble window: 80% of its 40 ground stops and delay programs started between noon and 6 PM.
- Short track record (18 flights), so its score leans on the airline's record at this hour.
Limited track record · 18 flights
Find Southwest 4642 fares Opens this date on Aviasales
#9 · Southwest 359
9:30 PM → 11:55 PM2h 25m nonstop
Local times, typical schedule. Last flown 2026-04-04.
68%
chance on time
On time (history)
62%
Cancelled
0.0%
Avg arrival delay
21 min
- Arrived on time 62% of the time (13 flights, Jun 2025 to May 2026).
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
- 70% of its delay minutes came from the plane arriving late from an earlier flight.
- Short track record (13 flights), so its score leans on the airline's record at this hour.
Limited track record · 13 flights
Find Southwest 359 fares Opens this date on Aviasales
#10 · Southwest 2373
7:30 PM → 9:55 PM2h 25m nonstop
Local times, typical schedule. Last flown 2026-05-30.
68%
chance on time
On time (history)
66%
Cancelled
0.0%
Avg arrival delay
20 min
- Arrived on time 66% of the time (47 flights, Jun 2025 to May 2026).
- Never cancelled in 47 scheduled flights.
- Departs outside HOU's trouble window (noon to 6 PM, when 80% of its 40 ground stops and delay programs started).
- Short track record (47 flights), so its score leans on the airline's record at this hour.
Limited track record · 47 flights
Find Southwest 2373 fares Opens this date on Aviasales

Airlines on this route

Season-adjusted chance of operating and arriving on time.

Southwest Airlines74%
1,844 flights · 74% on time as flown · 1.2% cancel

On time by departure time

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

Before 9 AM88%
520 flights · avg delay 6 min
9 AM to noon84%
213 flights · avg delay 8 min
Noon to 3 PM66%
339 flights · avg delay 21 min
3 to 6 PM64%
211 flights · avg delay 20 min
6 to 9 PM68%
416 flights · avg delay 18 min
After 9 PM64%
145 flights · avg delay 18 min

Best day: Saturday (83%). Worst: Sunday (75%).

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 aircraft44%
Airline (crew, maintenance, boarding)34%
Air traffic control and airport volume17%
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

HOU to MDW questions

What time of day is best to fly HOU to MDW?: Before 9 AM: 88% of flights arrived on time, against 64% for departures 3 to 6 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 HOU to MDW?: Southwest, with a season-adjusted 74% chance of operating and arriving on time over 1,844 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 HOU to MDW?: July (65% on time); the best was September (89%), 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 HOU

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