Chicago (MDW) to San Jose (SJC) · Dec 26, 2026 · return Jan 9, 2027

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.

Hotels in San Jose, California for these trips

Hotels: under a trip, hotels in San Jose, California for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in San Jose, California for these nights (Dec 26 – Jan 9, 2027 · 14 nights · 2 adults, 1 room): 3★ Sonesta San Jose - Milpitas, $1,344 total · 4★ Sonesta Silicon Valley, $1,757 total

All hotels in San Jose, California

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

2026-12-26 → 2027-01-09 · Axel-exclusive $411.25

• Southwest Airlines WN2386: MDW 2026-12-26 15:50:00 → SJC 2026-12-26 18:30:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-12-26 10:15:00 → SJC 2026-12-26 13:00:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $390.25

• Southwest Airlines WN4415 / WN3749: MDW 2026-12-26 15:15:00 → SJC 2026-12-26 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-12-26 15:15:00 → SAN 2026-12-26 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-12-26 19:30:00 → SJC 2026-12-26 21:00:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $390.25

• Southwest Airlines WN725 / WN364: MDW 2026-12-26 09:55:00 → SJC 2026-12-26 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-12-26 09:55:00 → BNA 2026-12-26 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-12-26 13:55:00 → SJC 2026-12-26 16:45:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $390.25

• Southwest Airlines WN2998 / WN3507: MDW 2026-12-26 18:05:00 → SJC 2026-12-26 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2026-12-26 18:05:00 → PHX 2026-12-26 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2026-12-26 22:20:00 → SJC 2026-12-26 23:20:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $390.25

• Southwest Airlines WN2905 / WN2917: MDW 2026-12-26 09:55:00 → SJC 2026-12-26 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-12-26 09:55:00 → BUR 2026-12-26 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-12-26 15:30:00 → SJC 2026-12-26 16:50:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $390.25

• Southwest Airlines WN1517 / WN2538: MDW 2026-12-26 10:05:00 → SJC 2026-12-26 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2026-12-26 10:05:00 → LAX 2026-12-26 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2026-12-26 14:45:00 → SJC 2026-12-26 16:00:00.
• Southwest Airlines WN3895: SJC 2027-01-09 23:00:00 → MDW 2027-01-10 05:00:00; nonstop; 240 minutes. Local airport times.

2026-12-26 → 2027-01-09 · Axel-exclusive $397.00

• Southwest Airlines WN3035: MDW 2026-12-26 09:55:00 → SJC 2026-12-26 12:35:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3818 / WN2518: SJC 2027-01-09 20:05:00 → MDW 2027-01-10 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
  • WN3818: SJC 2027-01-09 20:05:00 → LAX 2027-01-09 21:25:00; layover at LAX: 150 minutes.
  • WN2518: LAX 2027-01-09 23:55:00 → MDW 2027-01-10 05:55:00.

Explore this route

• All dates for this route
• Dec 25, 2026 · Return options
• Dec 27, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Dec 26, 2026 · return Jan 9, 2027: 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.

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