Travel with Axel,
get the best price.

Route overview: Chicago to San Jose (SJC) flight deals

Chicago → San Jose

Dec 3, 2026 · return Dec 5, 2026

MDW → SJC1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
3:50 pmMDW
4h 40m
Nonstop
6:30 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
9:55 amMDW
4h 40m
Nonstop
12:35 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
6:05 pmMDW
7h 15m
PHX · 1h 20m
11:20 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
10:05 amMDW
7h 55m
LAX · 2h 15m
4:00 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
9:55 amMDW
8h 50m
BNA · 2h 25m
4:45 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
10:10 amMDW
4h 45m
Nonstop
12:55 pmSJC
Southwest Airlines
8:05 pmSJC
7h 50m
LAX · 2h 30m
5:55 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
3:15 pmMDW
7h 45m
SAN · 1h 55m
9:00 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Thu, Dec 3 – Sat, Dec 5

Southwest Airlines
10:00 amMDW
6h 55m
LAS · 1h 25m
2:55 pmSJC
Southwest Airlines
11:00 pmSJC
4h
Nonstop
5:00 am+1MDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SJC

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this routeDec 2, 2026 → Dec 4, 2026Dec 4, 2026 → Dec 6, 2026
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Chicago to San Jose (SJC) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-03 → 2026-12-05Southwest AirlinesWN2386 / WN3895$350.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN3035 / WN3895$350.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN2998 + WN3507 / WN3895$335.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN1517 + WN2538 / WN3895$335.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN725 + WN364 / WN3895$335.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN3035 / WN3818 + WN2518$335.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN4415 + WN3749 / WN3895$335.002026-10-29T01:29:13Z
2026-12-03 → 2026-12-05Southwest AirlinesWN142 + WN1226 / WN3895$335.002026-10-29T01:29:13Z

2026-12-03 → 2026-12-05 · $350.00

  • Southwest Airlines WN2386: MDW 2026-12-03 15:50:00 → SJC 2026-12-03 18:30:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-03 → 2026-12-05 · $350.00

  • Southwest Airlines WN3035: MDW 2026-12-03 09:55:00 → SJC 2026-12-03 12:35:00; nonstop; 280 minutes. Local airport times.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-03 → 2026-12-05 · $335.00

  • Southwest Airlines WN2998 / WN3507: MDW 2026-12-03 18:05:00 → SJC 2026-12-03 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
    • WN2998: MDW 2026-12-03 18:05:00 → PHX 2026-12-03 21:00:00; layover at PHX: 80 minutes.
    • WN3507: PHX 2026-12-03 22:20:00 → SJC 2026-12-03 23:20:00.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-03 → 2026-12-05 · $335.00

  • Southwest Airlines WN1517 / WN2538: MDW 2026-12-03 10:05:00 → SJC 2026-12-03 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
    • WN1517: MDW 2026-12-03 10:05:00 → LAX 2026-12-03 12:30:00; layover at LAX: 135 minutes.
    • WN2538: LAX 2026-12-03 14:45:00 → SJC 2026-12-03 16:00:00.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-03 → 2026-12-05 · $335.00

  • Southwest Airlines WN725 / WN364: MDW 2026-12-03 09:55:00 → SJC 2026-12-03 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
    • WN725: MDW 2026-12-03 09:55:00 → BNA 2026-12-03 11:30:00; layover at BNA: 145 minutes.
    • WN364: BNA 2026-12-03 13:55:00 → SJC 2026-12-03 16:45:00.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-03 → 2026-12-05 · $335.00

  • Southwest Airlines WN3035: MDW 2026-12-03 10:10:00 → SJC 2026-12-03 12:55:00; nonstop; 285 minutes. Local airport times.
  • Southwest Airlines WN3818 / WN2518: SJC 2026-12-05 20:05:00 → MDW 2026-12-06 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
    • WN3818: SJC 2026-12-05 20:05:00 → LAX 2026-12-05 21:25:00; layover at LAX: 150 minutes.
    • WN2518: LAX 2026-12-05 23:55:00 → MDW 2026-12-06 05:55:00.

2026-12-03 → 2026-12-05 · $335.00

  • Southwest Airlines WN4415 / WN3749: MDW 2026-12-03 15:15:00 → SJC 2026-12-03 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
    • WN4415: MDW 2026-12-03 15:15:00 → SAN 2026-12-03 17:35:00; layover at SAN: 115 minutes.
    • WN3749: SAN 2026-12-03 19:30:00 → SJC 2026-12-03 21:00:00.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-03 → 2026-12-05 · $335.00

  • Southwest Airlines WN142 / WN1226: MDW 2026-12-03 10:00:00 → SJC 2026-12-03 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN142: MDW 2026-12-03 10:00:00 → LAS 2026-12-03 11:55:00; layover at LAS: 85 minutes.
    • WN1226: LAS 2026-12-03 13:20:00 → SJC 2026-12-03 14:55:00.
  • Southwest Airlines WN3895: SJC 2026-12-05 23:00:00 → MDW 2026-12-06 05:00:00; nonstop; 240 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to San Jose (SJC) · Dec 3, 2026 · return Dec 5, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to San Jose (SJC) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.