Oakland (OAK) to Chicago (MDW) · Nov 26, 2026 · return Dec 6, 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

2026-11-26 → 2026-12-06 · Axel-exclusive $408.00

• Southwest Airlines WN4605 / WN4990: OAK 2026-11-26 20:45:00 → MDW 2026-11-27 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2026-11-26 20:45:00 → LAS 2026-11-26 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2026-11-27 00:20:00 → MDW 2026-11-27 05:40:00.
• Southwest Airlines WN4415 / WN1144: MDW 2026-12-06 15:15:00 → OAK 2026-12-06 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-06 20:05:00 → OAK 2026-12-06 21:35:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $408.00

• Southwest Airlines WN3238 / WN2962: OAK 2026-11-26 13:35:00 → MDW 2026-11-26 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2026-11-26 13:35:00 → SAN 2026-11-26 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2026-11-26 16:05:00 → MDW 2026-11-26 22:00:00.
• Southwest Airlines WN4415 / WN1144: MDW 2026-12-06 15:15:00 → OAK 2026-12-06 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-06 20:05:00 → OAK 2026-12-06 21:35:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $408.00

• Southwest Airlines WN768 / WN2517: OAK 2026-11-26 15:40:00 → MDW 2026-11-27 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2026-11-26 15:40:00 → LAX 2026-11-26 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2026-11-26 18:45:00 → MDW 2026-11-27 00:40:00.
• Southwest Airlines WN4415 / WN1144: MDW 2026-12-06 15:15:00 → OAK 2026-12-06 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-06 20:05:00 → OAK 2026-12-06 21:35:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $408.00

• Southwest Airlines WN3217 / WN801: OAK 2026-11-26 08:30:00 → MDW 2026-11-26 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2026-11-26 08:30:00 → LGB 2026-11-26 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2026-11-26 11:35:00 → MDW 2026-11-26 17:20:00.
• Southwest Airlines WN4415 / WN1144: MDW 2026-12-06 15:15:00 → OAK 2026-12-06 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-06 20:05:00 → OAK 2026-12-06 21:35:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $408.00

• Southwest Airlines WN3203 / WN776: OAK 2026-11-26 11:25:00 → MDW 2026-11-26 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2026-11-26 11:25:00 → DEN 2026-11-26 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2026-11-26 18:05:00 → MDW 2026-11-26 21:30:00.
• Southwest Airlines WN4415 / WN1144: MDW 2026-12-06 15:15:00 → OAK 2026-12-06 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-06 20:05:00 → OAK 2026-12-06 21:35:00.

2026-11-26 → 2026-12-06 · Axel-exclusive $422.00

• Southwest Airlines WN3220: OAK 2026-11-26 23:50:00 → MDW 2026-11-27 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN4415 / WN1144: MDW 2026-12-06 15:15:00 → OAK 2026-12-06 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-06 15:15:00 → SAN 2026-12-06 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-06 20:05:00 → OAK 2026-12-06 21:35:00.

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: Oakland (OAK) to Chicago (MDW) · Nov 26, 2026 · return Dec 6, 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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