Reliable Flight Search results

1. Our best overall pick

   84% chance you arrive on time · 94% chance every connection works · 31 in legroom · planes about 10 years old · 7h 00m

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

   5:10 AM → 10:10 AM

   55

   score

   price

   live on Aviasales

   94%

   connections made

   84%

   arrive on time

   5:10 AM MDW → 7:05 AM LAS3h 55m

   Southwest 1859

   Boeing 737 MAX 8 · 2–9 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   89% on time · 0.8% cancel

   Connect in LAS · 1h 35m · 95% chance to make it · same ticket: the airline rebooks you if you miss it

   8:40 AM LAS → 10:10 AM SJC1h 30m

   Southwest 4615

   Boeing 737-800 or 737 MAX 8 · 2–21 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   90% on time · 0.3% cancel
   Why this ranks here

   Find this Southwest trip ↗Look for Southwest 1859 + Southwest 4615 on Aviasales

2. #2 · Nonstop · 4h 35m

   10:10 AM → 12:45 PM

   51

   score

   price

   live on Aviasales

   74%

   arrive on time

   10:10 AM MDW → 12:45 PM SJC4h 35m

   Southwest 1284

   Boeing 737-700 or 737 MAX 8 · 3–22 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   74% on time · 0.8% cancel
   Why this ranks here

   Find Southwest 1284 fares ↗Opens this date on Aviasales

3. #3 · 1 connection · 7h 40m · one ticket (Southwest)

   5:10 AM → 10:50 AM

   49

   score

   price

   live on Aviasales

   97%

   connections made

   81%

   arrive on time

   5:10 AM MDW → 7:05 AM LAS3h 55m

   Southwest 1859

   Boeing 737 MAX 8 · 2–9 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   89% on time · 0.8% cancel

   Connect in LAS · 2h 15m · 98% chance to make it · same ticket: the airline rebooks you if you miss it

   9:20 AM LAS → 10:50 AM SJC1h 30m

   Southwest 1685

   Boeing 737 MAX 8 · 1–11 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   83% on time · 0.3% cancel
   Why this ranks here

   Find this Southwest trip ↗Look for Southwest 1859 + Southwest 1685 on Aviasales

4. #4 · Nonstop · 4h 35m

   3:40 PM → 6:15 PM

   46

   score

   price

   live on Aviasales

   71%

   arrive on time

   3:40 PM MDW → 6:15 PM SJC4h 35m

   Southwest 826

   Boeing 737-700 · 15–22 yrs oldLegroom 31–36 in · 15.5–17 in wide · Economy (all seating types)

   72% on time · 1.0% cancel
   Why this ranks here

   Find Southwest 826 fares ↗Opens this date on Aviasales

5. #5 · 1 connection · 8h 00m · one ticket (Southwest)

   7:50 AM → 1:50 PM

   46

   score

   price

   live on Aviasales

   98%

   connections made

   80%

   arrive on time

   7:50 AM MDW → 9:50 AM LAS4h 00m

   Southwest 3285

   Boeing 737 MAX 8 or 737-800 · 1–10 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   92% on time · 0.7% cancel

   Connect in LAS · 2h 25m · 99% chance to make it · same ticket: the airline rebooks you if you miss it

   12:15 PM LAS → 1:50 PM SJC1h 35m

   Southwest 2409

   Boeing 737 MAX 8 or 737-700 · 4–22 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   82% on time · 0.2% cancel
   Why this ranks here

   Find this Southwest trip ↗Look for Southwest 3285 + Southwest 2409 on Aviasales

6. #6 · 1 connection · 6h 55m · one ticket (Southwest)

   5:25 AM → 10:20 AM

   46

   score

   price

   live on Aviasales

   84%

   connections made

   76%

   arrive on time

   5:25 AM MDW → 7:10 AM PHX3h 45m

   Southwest 3340

   Boeing 737 MAX 8 or 737-800 · 2–11 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   91% on time · 1.2% cancel

   Connect in PHX · 1h 00m · 85% chance to make it · same ticket: the airline rebooks you if you miss it

   8:10 AM PHX → 10:20 AM SJC2h 10m

   Southwest 3919

   Boeing 737 MAX 8 or 737-800 · 2–11 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   90% on time · 0.3% cancel
   Why this ranks here

   Find this Southwest trip ↗Look for Southwest 3340 + Southwest 3919 on Aviasales

7. #7 · 1 connection · 7h 20m · one ticket (Southwest)

   6:55 AM → 12:15 PM

   45

   score

   price

   live on Aviasales

   94%

   connections made

   78%

   arrive on time

   6:55 AM MDW → 8:45 AM PHX3h 50m

   Southwest 4631

   Boeing 737 MAX 8 or 737-800 · 3–14 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   88% on time · 1.3% cancel

   Connect in PHX · 1h 30m · 95% chance to make it · same ticket: the airline rebooks you if you miss it

   10:15 AM PHX → 12:15 PM SJC2h 00m

   Southwest 3045

   Boeing 737-800 or 737 MAX 8 · 3–21 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   83% on time · 0.3% cancel
   Why this ranks here

   Find this Southwest trip ↗Look for Southwest 4631 + Southwest 3045 on Aviasales

8. #8 · Nonstop · 4h 35m

   5:20 PM → 7:55 PM

   45

   score

   price

   live on Aviasales

   66%

   arrive on time

   5:20 PM MDW → 7:55 PM SJC4h 35m

   Southwest 1142

   Boeing 737 MAX 8 · 2–8 yrs oldLegroom 31–34 in · 15.5–17.8 in wide · Economy (all seating types)

   67% on time · 1.0% cancel
   Why this ranks here

   Find Southwest 1142 fares ↗Opens this date on Aviasales

9. #9 · 1 connection · 8h 50m · one ticket (Southwest)

   5:25 AM → 12:15 PM

   44

   score

   price

   live on Aviasales

   98%

   connections made

   82%

   arrive on time

   5:25 AM MDW → 7:10 AM PHX3h 45m

   Southwest 3340

   Boeing 737 MAX 8 or 737-800 · 2–11 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   91% on time · 1.2% cancel

   Connect in PHX · 3h 05m · 99% chance to make it · same ticket: the airline rebooks you if you miss it

   10:15 AM PHX → 12:15 PM SJC2h 00m

   Southwest 3045

   Boeing 737-800 or 737 MAX 8 · 3–21 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

   83% on time · 0.3% cancel
   Why this ranks here

   Find this Southwest trip ↗Look for Southwest 3340 + Southwest 3045 on Aviasales

10. #10 · 1 connection · 6h 20m · one ticket (Southwest)

    6:00 AM → 10:20 AM

    43

    score

    price

    live on Aviasales

    86%

    connections made

    77%

    arrive on time

    6:00 AM MDW → 7:40 AM DEN2h 40m

    Southwest 3262

    Boeing 737-700 or 737-800 · 3–22 yrs oldLegroom 31–36 in · 15.5–17.8 in wide · Economy (all seating types)

    90% on time · 0.9% cancel

    Connect in DEN · 1h 05m · 87% chance to make it · same ticket: the airline rebooks you if you miss it

    8:45 AM DEN → 10:20 AM SJC2h 35m

    Southwest 1173

    Boeing 737-700 · 20–24 yrs oldLegroom 31–36 in · 15.5–17 in wide · Economy (all seating types)

    89% on time · 0.6% cancel
    Why this ranks here

    Find this Southwest trip ↗Look for Southwest 3262 + Southwest 1173 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. Legroom is the seat pitch the airline or a seat-map source publishes for that aircraft and cabin; we never estimate it, and seat maps change, so check the airline’s seat map when you book.