Oakland (OAK) to Chicago (MDW) · Nov 23, 2026 · return Nov 30, 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

2026-11-23 → 2026-11-30 · Axel-exclusive $408.00

• Southwest Airlines WN3238 / WN2962: OAK 2026-11-23 13:35:00 → MDW 2026-11-23 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2026-11-23 13:35:00 → SAN 2026-11-23 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2026-11-23 16:05:00 → MDW 2026-11-23 22:00:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-30 15:45:00 → OAK 2026-11-30 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-30 15:45:00 → LAX 2026-11-30 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-30 20:00:00 → OAK 2026-11-30 21:15:00.

2026-11-23 → 2026-11-30 · Axel-exclusive $408.00

• Southwest Airlines WN3217 / WN801: OAK 2026-11-23 08:30:00 → MDW 2026-11-23 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2026-11-23 08:30:00 → LGB 2026-11-23 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2026-11-23 11:35:00 → MDW 2026-11-23 17:20:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-30 15:45:00 → OAK 2026-11-30 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-30 15:45:00 → LAX 2026-11-30 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-30 20:00:00 → OAK 2026-11-30 21:15:00.

2026-11-23 → 2026-11-30 · Axel-exclusive $408.00

• Southwest Airlines WN4605 / WN4990: OAK 2026-11-23 20:45:00 → MDW 2026-11-24 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2026-11-23 20:45:00 → LAS 2026-11-23 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2026-11-24 00:20:00 → MDW 2026-11-24 05:40:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-30 15:45:00 → OAK 2026-11-30 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-30 15:45:00 → LAX 2026-11-30 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-30 20:00:00 → OAK 2026-11-30 21:15:00.

2026-11-23 → 2026-11-30 · Axel-exclusive $408.00

• Southwest Airlines WN768 / WN2517: OAK 2026-11-23 15:40:00 → MDW 2026-11-24 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2026-11-23 15:40:00 → LAX 2026-11-23 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2026-11-23 18:45:00 → MDW 2026-11-24 00:40:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-30 15:45:00 → OAK 2026-11-30 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-30 15:45:00 → LAX 2026-11-30 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-30 20:00:00 → OAK 2026-11-30 21:15:00.

2026-11-23 → 2026-11-30 · Axel-exclusive $408.00

• Southwest Airlines WN3203 / WN776: OAK 2026-11-23 11:25:00 → MDW 2026-11-23 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2026-11-23 11:25:00 → DEN 2026-11-23 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2026-11-23 18:05:00 → MDW 2026-11-23 21:30:00.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-30 15:45:00 → OAK 2026-11-30 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-30 15:45:00 → LAX 2026-11-30 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-30 20:00:00 → OAK 2026-11-30 21:15:00.

2026-11-23 → 2026-11-30 · Axel-exclusive $418.00

• Southwest Airlines WN3220: OAK 2026-11-23 23:50:00 → MDW 2026-11-24 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2952 / WN1901: MDW 2026-11-30 15:45:00 → OAK 2026-11-30 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-30 15:45:00 → LAX 2026-11-30 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-30 20:00:00 → OAK 2026-11-30 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

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For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Nov 23, 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.
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