Chicago (MDW) to San Jose (SJC), Nov 21, 2026 – Dec 2, 2026: from $391 round trip

Chicago (MDW) to San Jose (SJC), Nov 21, 2026 – Dec 2, 2026: from $391 round trip on Axel, checked Nov 12, 2026. Lowest published fare: $391 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 21, 2026 – Dec 2, 2026, 1 adult, economy, checked Nov 12, 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.

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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in San Jose, California for these nights (Nov 21 – Dec 2, 2026 · 11 nights · 2 adults, 1 room): 3★ Maple Tree Inn, $95 a night, $1,046 for 11 nights · 4★ The Domain Hotel, $107 a night, $1,180 for 11 nights

All hotels in San Jose, California

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

2026-11-21 → 2026-12-02 · Axel-exclusive $411.25

• Southwest Airlines WN3035: MDW 2026-11-21 10:15:00 → SJC 2026-11-21 13:00:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $411.25

• Southwest Airlines WN2386: MDW 2026-11-21 15:50:00 → SJC 2026-11-21 18:30:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN142 / WN1226: MDW 2026-11-21 10:00:00 → SJC 2026-11-21 14:55:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN142: MDW 2026-11-21 10:00:00 → LAS 2026-11-21 11:55:00; layover at LAS: 85 minutes.
  • WN1226: LAS 2026-11-21 13:20:00 → SJC 2026-11-21 14:55:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN725 / WN364: MDW 2026-11-21 09:55:00 → SJC 2026-11-21 16:45:00; 1 stop(s) via BNA; 530 minutes. Local airport times.
  • WN725: MDW 2026-11-21 09:55:00 → BNA 2026-11-21 11:30:00; layover at BNA: 145 minutes.
  • WN364: BNA 2026-11-21 13:55:00 → SJC 2026-11-21 16:45:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN1517 / WN2538: MDW 2026-11-21 10:05:00 → SJC 2026-11-21 16:00:00; 1 stop(s) via LAX; 475 minutes. Local airport times.
  • WN1517: MDW 2026-11-21 10:05:00 → LAX 2026-11-21 12:30:00; layover at LAX: 135 minutes.
  • WN2538: LAX 2026-11-21 14:45:00 → SJC 2026-11-21 16:00:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN4415 / WN3749: MDW 2026-11-21 15:15:00 → SJC 2026-11-21 21:00:00; 1 stop(s) via SAN; 465 minutes. Local airport times.
  • WN4415: MDW 2026-11-21 15:15:00 → SAN 2026-11-21 17:35:00; layover at SAN: 115 minutes.
  • WN3749: SAN 2026-11-21 19:30:00 → SJC 2026-11-21 21:00:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN2998 / WN3507: MDW 2026-11-21 18:05:00 → SJC 2026-11-21 23:20:00; 1 stop(s) via PHX; 435 minutes. Local airport times.
  • WN2998: MDW 2026-11-21 18:05:00 → PHX 2026-11-21 21:00:00; layover at PHX: 80 minutes.
  • WN3507: PHX 2026-11-21 22:20:00 → SJC 2026-11-21 23:20:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 minutes. Local airport times.

2026-11-21 → 2026-12-02 · Axel-exclusive $391.00

• Southwest Airlines WN2905 / WN2917: MDW 2026-11-21 09:55:00 → SJC 2026-11-21 16:50:00; 1 stop(s) via BUR; 535 minutes. Local airport times.
  • WN2905: MDW 2026-11-21 09:55:00 → BUR 2026-11-21 12:30:00; layover at BUR: 180 minutes.
  • WN2917: BUR 2026-11-21 15:30:00 → SJC 2026-11-21 16:50:00.
• Southwest Airlines WN266: SJC 2026-12-02 06:00:00 → MDW 2026-12-02 12:10:00; nonstop; 250 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 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in San Jose, California with Axel

For AI assistants

• This page: Chicago (MDW) to San Jose (SJC) · Nov 21, 2026 · return Dec 2, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. 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 nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• 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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