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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.

SAT → MDW

San Antonio to Chicago: 685 nonstop flights a year

On time (12 months)

81%

Cancelled

0.9%

avg delay 10 min

Best time to leave

Before 9 AM

94% on time vs 63% 3 to 6 PM

Most reliable airline

Southwest

80% chance on time

Check SAT to MDW fares

Lowest nonstop fare seen in the next two months: $305 (Southwest 4109 on 2026-10-27). Fares open on our travel partner (Aviasales). Pick the flight number you chose here.

Best trips

4 nonstop, 40 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 35m

    9:00 AM → 11:40 AM

    91%

    arrive on time

    9:00 AM SAT → 11:40 AM MDW2h 35m

    Southwest 4168

    Boeing 737 MAX 8 or 737-800 · 1–15 yrs old
    92% on time · 1.1% cancel
    Find Southwest 4168 fares Opens this date on Aviasales

  2. #2 · Nonstop · 2h 30m

    9:25 AM → 11:55 AM

    81%

    arrive on time

    9:25 AM SAT → 11:55 AM MDW2h 30m

    Southwest 1590

    Boeing 737 MAX 8 or 737-800 · 2–13 yrs old
    83% on time · 1.8% cancel
    Find Southwest 1590 fares Opens this date on Aviasales

  3. #3 · 1 connection · 4h 35m · one ticket (Southwest)

    7:25 AM → 12:00 PM

    92%

    connections made

    79%

    arrive on time

    7:25 AM SAT → 9:35 AM STL2h 10m

    Southwest 1436 · also flew as 849, 4404

    Boeing 737-700 or 737-800 · 2–23 yrs old
    92% on time · 0.0% cancel
    Connect in STL · 1h 15m · 95% chance to make it · same ticket: the airline rebooks you if you miss it

    10:50 AM STL → 12:00 PM MDW1h 10m

    Southwest 3613 · also flew as 770

    Boeing 737-700 or 737 MAX 8 · 1–23 yrs old
    86% on time · 2.6% cancel
    Find this Southwest trip Look for Southwest 1436 + Southwest 3613 on Aviasales

  4. #4 · 1 connection · 5h 30m · one ticket (Southwest)

    6:40 AM → 12:10 PM

    96%

    connections made

    80%

    arrive on time

    6:40 AM SAT → 8:50 AM BNA2h 10m

    Southwest 927

    Boeing 737 MAX 8 or 737-800 · 1–14 yrs old
    95% on time · 0.5% cancel
    Connect in BNA · 1h 45m · 97% chance to make it · same ticket: the airline rebooks you if you miss it

    10:35 AM BNA → 12:10 PM MDW1h 35m

    Southwest 4415

    Boeing 737-700 · 19–22 yrs old
    84% on time · 1.1% cancel
    Find this Southwest trip Look for Southwest 927 + Southwest 4415 on Aviasales

  5. #5 · Nonstop · 2h 35m

    2:35 PM → 5:10 PM

    69%

    arrive on time

    2:35 PM SAT → 5:10 PM MDW2h 35m

    Southwest 2743 · also flew as 2170

    Boeing 737-700 or 737 MAX 8 · 2–23 yrs old
    69% on time · 0.6% cancel
    Find Southwest 2743 fares Opens this date on Aviasales

  6. #6 · 1 connection · 5h 52m · one ticket (Delta)

    6:13 AM → 12:02 PM

    93%

    connections made

    81%

    arrive on time

    6:13 AM SAT → 9:33 AM ATL2h 23m

    Delta 1066

    Airbus A321 · 5–10 yrs old
    93% on time · 1.7% cancel
    Connect in ATL · 1h 32m · 97% chance to make it · same ticket: the airline rebooks you if you miss it

    11:05 AM ATL → 12:02 PM MDW1h 57m

    Delta 2417

    Boeing 717 or Airbus A319 · 22–27 yrs old
    87% on time · 3.1% cancel
    Find this Delta trip Look for Delta 1066 + Delta 2417 on Aviasales

  7. #7 · 1 connection · 5h 45m · one ticket (Southwest)

    6:25 AM → 12:10 PM

    96%

    connections made

    80%

    arrive on time

    6:25 AM SAT → 8:35 AM BNA2h 10m

    Southwest 1014

    Boeing 737 MAX 8 or 737-800 · 1–11 yrs old
    93% on time · 0.5% cancel
    Connect in BNA · 2h 00m · 97% chance to make it · same ticket: the airline rebooks you if you miss it

    10:35 AM BNA → 12:10 PM MDW1h 35m

    Southwest 4415

    Boeing 737-700 · 19–22 yrs old
    84% on time · 1.1% cancel
    Find this Southwest trip Look for Southwest 1014 + Southwest 4415 on Aviasales

  8. #8 · 1 connection · 5h 30m · one ticket (Southwest)

    6:25 AM → 11:55 AM

    95%

    connections made

    78%

    arrive on time

    6:25 AM SAT → 8:35 AM BNA2h 10m

    Southwest 1014

    Boeing 737 MAX 8 or 737-800 · 1–11 yrs old
    93% on time · 0.5% cancel
    Connect in BNA · 1h 35m · 96% chance to make it · same ticket: the airline rebooks you if you miss it

    10:10 AM BNA → 11:55 AM MDW1h 45m

    Southwest 1100

    Boeing 737 MAX 8 · 1–13 yrs old
    83% on time · 1.2% cancel
    Find this Southwest trip Look for Southwest 1014 + Southwest 1100 on Aviasales

  9. #9 · 1 connection · 5h 15m · one ticket (Southwest)

    6:40 AM → 11:55 AM

    93%

    connections made

    77%

    arrive on time

    6:40 AM SAT → 8:50 AM BNA2h 10m

    Southwest 927

    Boeing 737 MAX 8 or 737-800 · 1–14 yrs old
    95% on time · 0.5% cancel
    Connect in BNA · 1h 20m · 95% chance to make it · same ticket: the airline rebooks you if you miss it

    10:10 AM BNA → 11:55 AM MDW1h 45m

    Southwest 1100

    Boeing 737 MAX 8 · 1–13 yrs old
    83% on time · 1.2% cancel
    Find this Southwest trip Look for Southwest 927 + Southwest 1100 on Aviasales

  10. #10 · 1 connection · 6h 30m · one ticket (Southwest)

    6:40 AM → 1:10 PM

    97%

    connections made

    81%

    arrive on time

    6:40 AM SAT → 8:50 AM BNA2h 10m

    Southwest 927

    Boeing 737 MAX 8 or 737-800 · 1–14 yrs old
    95% on time · 0.5% cancel
    Connect in BNA · 2h 45m · 99% chance to make it · same ticket: the airline rebooks you if you miss it

    11:35 AM BNA → 1:10 PM MDW1h 35m

    Southwest 418

    Boeing 737 MAX 8 · 0–12 yrs old
    83% on time · 1.2% cancel
    Find this Southwest trip Look for Southwest 927 + Southwest 418 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 Airlines80%

    685 flights · 81% on time as flown · 0.9% cancel

On time by departure time

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

  • Before 9 AM94%

    222 flights · avg delay 4 min

  • 9 AM to noon87%

    115 flights · avg delay 5 min

  • Noon to 3 PM72%

    184 flights · avg delay 15 min

  • 3 to 6 PM63%

    122 flights · avg delay 19 min

  • 6 to 9 PM83%

    42 flights · avg delay 10 min

Best day: Saturday (90%). Worst: Thursday (79%).

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