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ATIS Alerts Smart Flight Search

Find the flight least likely to be delayed

Beta

We rank real flight numbers by how often they flew and arrived on time over the last 12 months, adjusted for your travel month and departure time, then check nearby airports and calmer connections. US airlines and airports.

MDW → SAT

Chicago to San Antonio: 685 nonstop flights a year

On time (12 months)

78%

Cancelled

1.0%

avg delay 14 min

Best time to leave

Before 9 AM

85% on time vs 66% after 9 PM

Most reliable airline

Southwest

77% chance on time

Check MDW to SAT fares

Lowest nonstop fare seen in the next two months: $283 (Southwest 3426 on 2026-10-21). Fares open on our travel partner (Aviasales). Pick the flight number you chose here.

Best trips

3 nonstop, 43 with 1 connection. Best overall weighs the chance you arrive on time as booked, connection odds, travel time and separate tickets.

  1. Best overall#1 · Nonstop · 2h 50m

    10:10 AM → 1:00 PM

    80%

    arrive on time

    10:10 AM MDW → 1:00 PM SAT2h 50m

    Southwest 2168 · also flew as 2471

    Boeing 737-700 or 737-800 · 3–22 yrs old
    81% on time · 1.1% cancel
    Find Southwest 2168 fares Opens this date on Aviasales

  2. #2 · 1 connection · 5h 08m · one ticket (Southwest)

    5:30 AM → 10:40 AM

    89%

    connections made

    82%

    arrive on time

    5:30 AM MDW → 6:55 AM BNA1h 25m

    Southwest 116 · also flew as 683

    Boeing 737 MAX 8 or 737-800 · 1–14 yrs old
    94% on time · 1.5% cancel
    Connect in BNA · 1h 10m · 91% chance to make it · same ticket: the airline rebooks you if you miss it

    8:05 AM BNA → 10:40 AM SAT2h 33m

    Southwest 478

    Boeing 737-700 or 737 MAX 8 · 1–22 yrs old
    92% on time · 0.5% cancel
    Find this Southwest trip Look for Southwest 116 + Southwest 478 on Aviasales

  3. #3 · Nonstop · 2h 50m

    9:40 PM → 12:30 AM

    73%

    arrive on time

    9:40 PM MDW → 12:30 AM SAT2h 50m

    Southwest 2350

    Boeing 737-700 or 737 MAX 8 · 1–23 yrs old
    74% on time · 1.2% cancel
    Find Southwest 2350 fares Opens this date on Aviasales

  4. #4 · 1 connection · 4h 55m · one ticket (Southwest)

    5:30 AM → 10:25 AM

    92%

    connections made

    81%

    arrive on time

    5:30 AM MDW → 7:55 AM DAL2h 25m

    Southwest 1059 · also flew as 7

    Boeing 737 MAX 8 or 737-700 · 2–23 yrs old
    95% on time · 1.4% cancel
    Connect in DAL · 1h 15m · 94% chance to make it · same ticket: the airline rebooks you if you miss it

    9:10 AM DAL → 10:25 AM SAT1h 15m

    Southwest 120

    Boeing 737 MAX 8 · 1–10 yrs old
    88% on time · 1.0% cancel
    Find this Southwest trip Look for Southwest 1059 + Southwest 120 on Aviasales

  5. #5 · 1 connection · 5h 10m · one ticket (Southwest)

    5:30 AM → 10:40 AM

    93%

    connections made

    81%

    arrive on time

    5:30 AM MDW → 7:55 AM DAL2h 25m

    Southwest 1059 · also flew as 7

    Boeing 737 MAX 8 or 737-700 · 2–23 yrs old
    95% on time · 1.4% cancel
    Connect in DAL · 1h 30m · 96% chance to make it · same ticket: the airline rebooks you if you miss it

    9:25 AM DAL → 10:40 AM SAT1h 15m

    Southwest 2042

    Boeing 737 MAX 8 · 1–22 yrs old
    87% on time · 1.5% cancel
    Find this Southwest trip Look for Southwest 1059 + Southwest 2042 on Aviasales

  6. #6 · 1 connection · 5h 30m · one ticket (Southwest)

    6:30 AM → 12:00 PM

    93%

    connections made

    79%

    arrive on time

    6:30 AM MDW → 9:25 AM HOU2h 55m

    Southwest 150

    Boeing 737 MAX 8 or 737-800 · 2–16 yrs old
    87% on time · 1.0% cancel
    Connect in HOU · 1h 30m · 94% chance to make it · same ticket: the airline rebooks you if you miss it

    10:55 AM HOU → 12:00 PM SAT1h 05m

    Southwest 1682

    Boeing 737-700 · 17–23 yrs old
    85% on time · 0.0% cancel
    Find this Southwest trip Look for Southwest 150 + Southwest 1682 on Aviasales

  7. #7 · 1 connection · 7h 00m · one ticket (Southwest)

    5:00 AM → 12:00 PM

    98%

    connections made

    84%

    arrive on time

    5:00 AM MDW → 7:40 AM HOU2h 40m

    Southwest 3102

    Boeing 737-700 · 16–22 yrs old
    85% on time · 1.1% cancel
    Connect in HOU · 3h 15m · 99% chance to make it · same ticket: the airline rebooks you if you miss it

    10:55 AM HOU → 12:00 PM SAT1h 05m

    Southwest 1682

    Boeing 737-700 · 17–23 yrs old
    85% on time · 0.0% cancel
    Find this Southwest trip Look for Southwest 3102 + Southwest 1682 on Aviasales

  8. #8 · 1 connection · 5h 20m · one ticket (Southwest)

    5:05 AM → 10:25 AM

    89%

    connections made

    79%

    arrive on time

    5:05 AM MDW → 7:35 AM DAL2h 30m

    Southwest 915

    Boeing 737 MAX 8 · 1–22 yrs old
    89% on time · 1.6% cancel
    Connect in DAL · 1h 35m · 92% chance to make it · same ticket: the airline rebooks you if you miss it

    9:10 AM DAL → 10:25 AM SAT1h 15m

    Southwest 120

    Boeing 737 MAX 8 · 1–10 yrs old
    88% on time · 1.0% cancel
    Find this Southwest trip Look for Southwest 915 + Southwest 120 on Aviasales

  9. #9 · 1 connection · 5h 35m · one ticket (Southwest)

    5:05 AM → 10:40 AM

    91%

    connections made

    79%

    arrive on time

    5:05 AM MDW → 7:35 AM DAL2h 30m

    Southwest 915

    Boeing 737 MAX 8 · 1–22 yrs old
    89% on time · 1.6% cancel
    Connect in DAL · 1h 50m · 94% chance to make it · same ticket: the airline rebooks you if you miss it

    9:25 AM DAL → 10:40 AM SAT1h 15m

    Southwest 2042

    Boeing 737 MAX 8 · 1–22 yrs old
    87% on time · 1.5% cancel
    Find this Southwest trip Look for Southwest 915 + Southwest 2042 on Aviasales

  10. #10 · 1 connection · 5h 05m · one ticket (Southwest)

    6:55 AM → 12:00 PM

    91%

    connections made

    78%

    arrive on time

    6:55 AM MDW → 9:35 AM HOU2h 40m

    Southwest 455

    Boeing 737 MAX 8 · 1–11 yrs old
    86% on time · 0.9% cancel
    Connect in HOU · 1h 20m · 92% chance to make it · same ticket: the airline rebooks you if you miss it

    10:55 AM HOU → 12:00 PM SAT1h 05m

    Southwest 1682

    Boeing 737-700 · 17–23 yrs old
    85% on time · 0.0% cancel
    Find this Southwest trip Look for Southwest 455 + Southwest 1682 on Aviasales

Aircraft and ages come from the planes each flight number actually flew in the last 3 months of data (FAA registry build years); airlines can swap planes.

Airlines on this route

Season-adjusted chance of operating and arriving on time.

  • Southwest Airlines77%

    685 flights · 78% on time as flown · 1.0% cancel

On time by departure time

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

  • Before 9 AM85%

    239 flights · avg delay 7 min

  • 9 AM to noon81%

    109 flights · avg delay 8 min

  • 3 to 6 PM70%

    76 flights · avg delay 24 min

  • 6 to 9 PM80%

    90 flights · avg delay 12 min

  • After 9 PM66%

    163 flights · avg delay 24 min

Best day: Wednesday (83%). Worst: Friday (73%).

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