Chicago (MDW) to San Jose (SJC), Nov 14–16, 2026: from $335 round trip
Chicago (MDW) to San Jose (SJC), Nov 14–16, 2026: from $335 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $335 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 14–16, 2026, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN3035 / WN4230 | 10:15:00→13:00:00 4h 45m nonstop · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $350.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN2386 / WN4230 | 15:50:00→18:30:00 4h 40m nonstop · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $350.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN3035 / WN3883 + WN2133 | 10:10:00→12:55:00 4h 45m nonstop · 07:45:00→17:00:00 7h 15m 1 stop via HOU | Axel-exclusive $335.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN142 + WN1226 / WN4230 | 10:00:00→14:55:00 6h 55m 1 stop via LAS · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $335.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN2998 + WN3507 / WN4230 | 18:05:00→23:20:00 7h 15m 1 stop via PHX · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $335.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN2905 + WN2917 / WN4230 | 09:55:00→16:50:00 8h 55m 1 stop via BUR · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $335.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN4415 + WN3749 / WN4230 | 15:15:00→21:00:00 7h 45m 1 stop via SAN · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $335.00 | 2026-10-29T01:29:13Z |
| 2026-11-14 → 2026-11-16 | Southwest Airlines | WN1517 + WN2538 / WN4230 | 10:05:00→16:00:00 7h 55m 1 stop via LAX · 23:00:00→05:00:00 4h 00m nonstop | Axel-exclusive $335.00 | 2026-10-29T01:29:13Z |
Hotels in San Jose, California for these trips
Hotels: under a trip, hotels in San Jose, California for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in San Jose, California for these nights (Nov 14–16, 2026 · 2 nights · 2 adults, 1 room): 3★ AC Hotel by Marriott San Jose Downtown · 4★ San Jose Marriott
All hotels in San Jose, California
Route overview: Chicago to San Jose (SJC) flight deals
2026-11-14 → 2026-11-16 · Axel-exclusive $350.00
- Southwest Airlines WN3035: MDW 2026-11-14 10:15:00 → SJC 2026-11-14 13:00:00; nonstop; 285 minutes. Local airport times.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
2026-11-14 → 2026-11-16 · Axel-exclusive $350.00
- Southwest Airlines WN2386: MDW 2026-11-14 15:50:00 → SJC 2026-11-14 18:30:00; nonstop; 280 minutes. Local airport times.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
2026-11-14 → 2026-11-16 · Axel-exclusive $335.00
- Southwest Airlines WN3035: MDW 2026-11-14 10:10:00 → SJC 2026-11-14 12:55:00; nonstop; 285 minutes. Local airport times.
- Southwest Airlines WN3883 / WN2133: SJC 2026-11-16 07:45:00 → MDW 2026-11-16 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
- WN3883: SJC 2026-11-16 07:45:00 → HOU 2026-11-16 13:20:00; layover at HOU: 75 minutes.
- WN2133: HOU 2026-11-16 14:35:00 → MDW 2026-11-16 17:00:00.
2026-11-14 → 2026-11-16 · Axel-exclusive $335.00
- Southwest Airlines WN142 / WN1226: MDW 2026-11-14 10:00:00 → SJC 2026-11-14 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
- WN142: MDW 2026-11-14 10:00:00 → LAS 2026-11-14 11:55:00; layover at LAS: 85 minutes.
- WN1226: LAS 2026-11-14 13:20:00 → SJC 2026-11-14 14:55:00.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
2026-11-14 → 2026-11-16 · Axel-exclusive $335.00
- Southwest Airlines WN2998 / WN3507: MDW 2026-11-14 18:05:00 → SJC 2026-11-14 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
- WN2998: MDW 2026-11-14 18:05:00 → PHX 2026-11-14 21:00:00; layover at PHX: 80 minutes.
- WN3507: PHX 2026-11-14 22:20:00 → SJC 2026-11-14 23:20:00.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
2026-11-14 → 2026-11-16 · Axel-exclusive $335.00
- Southwest Airlines WN2905 / WN2917: MDW 2026-11-14 09:55:00 → SJC 2026-11-14 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
- WN2905: MDW 2026-11-14 09:55:00 → BUR 2026-11-14 12:30:00; layover at BUR: 180 minutes.
- WN2917: BUR 2026-11-14 15:30:00 → SJC 2026-11-14 16:50:00.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
2026-11-14 → 2026-11-16 · Axel-exclusive $335.00
- Southwest Airlines WN4415 / WN3749: MDW 2026-11-14 15:15:00 → SJC 2026-11-14 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
- WN4415: MDW 2026-11-14 15:15:00 → SAN 2026-11-14 17:35:00; layover at SAN: 115 minutes.
- WN3749: SAN 2026-11-14 19:30:00 → SJC 2026-11-14 21:00:00.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
2026-11-14 → 2026-11-16 · Axel-exclusive $335.00
- Southwest Airlines WN1517 / WN2538: MDW 2026-11-14 10:05:00 → SJC 2026-11-14 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
- WN1517: MDW 2026-11-14 10:05:00 → LAX 2026-11-14 12:30:00; layover at LAX: 135 minutes.
- WN2538: LAX 2026-11-14 14:45:00 → SJC 2026-11-14 16:00:00.
- Southwest Airlines WN4230: SJC 2026-11-16 23:00:00 → MDW 2026-11-17 05:00:00; nonstop; 240 minutes. Local airport times.
Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.
Explore this route
- All dates for this route
- Nov 13, 2026 · Return options
- Nov 15, 2026 · Return options
- Hotels in San Jose, California with Axel
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- This page: Chicago (MDW) to San Jose (SJC) · Nov 14, 2026 · return Nov 16, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in San Jose, California for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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