Oakland (OAK) to Chicago (MDW), Nov 11–16, 2026: from $340 round trip

Lowest published fare: $340 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 11–16, 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.

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

2026-11-11 → 2026-11-16 · Axel-exclusive $340.00

• Southwest Airlines WN4605 / WN4990: OAK 2026-11-11 20:45:00 → MDW 2026-11-12 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2026-11-11 20:45:00 → LAS 2026-11-11 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2026-11-12 00:20:00 → MDW 2026-11-12 05:40:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-16 15:45:00 → OAK 2026-11-16 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-16 15:45:00 → LAX 2026-11-16 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-16 20:00:00 → OAK 2026-11-16 21:15:00.

2026-11-11 → 2026-11-16 · Axel-exclusive $340.00

• Southwest Airlines WN3217 / WN801: OAK 2026-11-11 08:30:00 → MDW 2026-11-11 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2026-11-11 08:30:00 → LGB 2026-11-11 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2026-11-11 11:35:00 → MDW 2026-11-11 17:20:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-16 15:45:00 → OAK 2026-11-16 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-16 15:45:00 → LAX 2026-11-16 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-16 20:00:00 → OAK 2026-11-16 21:15:00.

2026-11-11 → 2026-11-16 · Axel-exclusive $340.00

• Southwest Airlines WN4674 / WN4349: OAK 2026-11-11 07:45:00 → MDW 2026-11-11 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
  • WN4674: OAK 2026-11-11 07:45:00 → SLC 2026-11-11 10:25:00; layover at SLC: 205 minutes.
  • WN4349: SLC 2026-11-11 13:50:00 → MDW 2026-11-11 17:45:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-16 15:45:00 → OAK 2026-11-16 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-16 15:45:00 → LAX 2026-11-16 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-16 20:00:00 → OAK 2026-11-16 21:15:00.

2026-11-11 → 2026-11-16 · Axel-exclusive $340.00

• Southwest Airlines WN3203 / WN776: OAK 2026-11-11 11:25:00 → MDW 2026-11-11 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2026-11-11 11:25:00 → DEN 2026-11-11 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2026-11-11 18:05:00 → MDW 2026-11-11 21:30:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-16 15:45:00 → OAK 2026-11-16 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-16 15:45:00 → LAX 2026-11-16 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-16 20:00:00 → OAK 2026-11-16 21:15:00.

2026-11-11 → 2026-11-16 · Axel-exclusive $340.00

• Southwest Airlines WN768 / WN2517: OAK 2026-11-11 15:40:00 → MDW 2026-11-12 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2026-11-11 15:40:00 → LAX 2026-11-11 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2026-11-11 18:45:00 → MDW 2026-11-12 00:40:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-16 15:45:00 → OAK 2026-11-16 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-16 15:45:00 → LAX 2026-11-16 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-16 20:00:00 → OAK 2026-11-16 21:15:00.

2026-11-11 → 2026-11-16 · Axel-exclusive $350.00

• Southwest Airlines WN2871: OAK 2026-11-11 06:30:00 → MDW 2026-11-11 12:30:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-16 15:45:00 → OAK 2026-11-16 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-16 15:45:00 → LAX 2026-11-16 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-16 20:00:00 → OAK 2026-11-16 21:15:00.

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 10, 2026 · Return options
• Nov 12, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Nov 11, 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.
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