San Jose (SJC) to Chicago (MDW), Nov 26–30, 2026: from $466 round trip

San Jose (SJC) to Chicago (MDW), Nov 26–30, 2026: from $466 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $466 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 26–30, 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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago for these nights (Nov 26–30, 2026 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

2026-11-26 → 2026-11-30 · Axel-exclusive $490.00

• Southwest Airlines WN3895: SJC 2026-11-26 23:00:00 → MDW 2026-11-27 05:00:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $490.00

• Southwest Airlines WN266: SJC 2026-11-26 06:00:00 → MDW 2026-11-26 12:10:00; nonstop; 250 minutes. Local airport times.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $465.50

• Southwest Airlines WN3877 / WN776: SJC 2026-11-26 13:40:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 350 minutes. Local airport times.
  • WN3877: SJC 2026-11-26 13:40:00 → DEN 2026-11-26 17:05:00; layover at DEN: 60 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $465.50

• Southwest Airlines WN2612 / WN4975: SJC 2026-11-26 20:45:00 → MDW 2026-11-27 06:05:00; 1 stop(s) via SEA; 440 minutes. Local airport times.
  • WN2612: SJC 2026-11-26 20:45:00 → SEA 2026-11-26 23:10:00; layover at SEA: 65 minutes.
  • WN4975: SEA 2026-11-27 00:15:00 → MDW 2026-11-27 06:05:00.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $465.50

• Southwest Airlines WN3901 / WN696: SJC 2026-11-26 07:15:00 → MDW 2026-11-26 17:05:00; 1 stop(s) via PDX; 470 minutes. Local airport times.
  • WN3901: SJC 2026-11-26 07:15:00 → PDX 2026-11-26 09:05:00; layover at PDX: 135 minutes.
  • WN696: PDX 2026-11-26 11:20:00 → MDW 2026-11-26 17:05:00.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $465.50

• Southwest Airlines WN3883 / WN2133: SJC 2026-11-26 07:45:00 → MDW 2026-11-26 17:00:00; 1 stop(s) via HOU; 435 minutes. Local airport times.
  • WN3883: SJC 2026-11-26 07:45:00 → HOU 2026-11-26 13:20:00; layover at HOU: 75 minutes.
  • WN2133: HOU 2026-11-26 14:35:00 → MDW 2026-11-26 17:00:00.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $465.50

• Southwest Airlines WN3818 / WN2518: SJC 2026-11-26 20:05:00 → MDW 2026-11-27 05:55:00; 1 stop(s) via LAX; 470 minutes. Local airport times.
  • WN3818: SJC 2026-11-26 20:05:00 → LAX 2026-11-26 21:25:00; layover at LAX: 150 minutes.
  • WN2518: LAX 2026-11-26 23:55:00 → MDW 2026-11-27 05:55:00.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 minutes. Local airport times.

2026-11-26 → 2026-11-30 · Axel-exclusive $465.50

• Southwest Airlines WN433 / WN801: SJC 2026-11-26 07:20:00 → MDW 2026-11-26 17:20:00; 1 stop(s) via LGB; 480 minutes. Local airport times.
  • WN433: SJC 2026-11-26 07:20:00 → LGB 2026-11-26 08:35:00; layover at LGB: 180 minutes.
  • WN801: LGB 2026-11-26 11:35:00 → MDW 2026-11-26 17:20:00.
• Southwest Airlines WN3035: MDW 2026-11-30 10:10:00 → SJC 2026-11-30 12:55:00; nonstop; 285 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 25, 2026 · Return options
• Nov 27, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Jose (SJC) to Chicago (MDW) · Nov 26, 2026 · return Nov 30, 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 Chicago 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.
• 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 San Francisco Bay Area to Chicago (MDW) 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.

Feedback (optional): Missing info · Axel issue