Oakland (OAK) to Chicago (MDW), Nov 20–22, 2026: from $175 one way

Oakland (OAK) to Chicago (MDW), Nov 20–22, 2026: from $175 one way on Axel, checked Oct 29, 2026. Lowest published fare: $175 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 20, 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

2026-11-20 · one way · Axel-exclusive $185.00

• Southwest Airlines WN2871: OAK 2026-11-20 06:30:00 → MDW 2026-11-20 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-22 · one way · Axel-exclusive $185.00

• Southwest Airlines WN2871: OAK 2026-11-22 06:30:00 → MDW 2026-11-22 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $185.00

• Southwest Airlines WN2871: OAK 2026-11-21 06:30:00 → MDW 2026-11-21 12:30:00; nonstop; 240 minutes. Local airport times.

2026-11-22 · one way · Axel-exclusive $185.00

• Southwest Airlines WN3220: OAK 2026-11-22 23:50:00 → MDW 2026-11-23 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-20 · one way · Axel-exclusive $185.00

• Southwest Airlines WN3220: OAK 2026-11-20 23:50:00 → MDW 2026-11-21 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $185.00

• Southwest Airlines WN3220: OAK 2026-11-21 23:50:00 → MDW 2026-11-22 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $175.00

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

2026-11-20 · one way · Axel-exclusive $175.00

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

2026-11-21 · one way · Axel-exclusive $175.00

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

2026-11-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3203 / WN776: OAK 2026-11-22 11:25:00 → MDW 2026-11-22 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2026-11-22 11:25:00 → DEN 2026-11-22 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2026-11-22 18:05:00 → MDW 2026-11-22 21:30:00.

2026-11-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3238 / WN2962: OAK 2026-11-22 13:35:00 → MDW 2026-11-22 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2026-11-22 13:35:00 → SAN 2026-11-22 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2026-11-22 16:05:00 → MDW 2026-11-22 22:00:00.

2026-11-21 · one way · Axel-exclusive $175.00

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

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3217 / WN801: OAK 2026-11-20 08:30:00 → MDW 2026-11-20 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2026-11-20 08:30:00 → LGB 2026-11-20 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2026-11-20 11:35:00 → MDW 2026-11-20 17:20:00.

2026-11-20 · one way · Axel-exclusive $175.00

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

2026-11-21 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3203 / WN776: OAK 2026-11-21 11:25:00 → MDW 2026-11-21 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2026-11-21 11:25:00 → DEN 2026-11-21 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2026-11-21 18:05:00 → MDW 2026-11-21 21:30:00.

2026-11-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN4674 / WN4349: OAK 2026-11-22 07:45:00 → MDW 2026-11-22 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
  • WN4674: OAK 2026-11-22 07:45:00 → SLC 2026-11-22 10:25:00; layover at SLC: 205 minutes.
  • WN4349: SLC 2026-11-22 13:50:00 → MDW 2026-11-22 17:45:00.

2026-11-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN3217 / WN801: OAK 2026-11-22 08:30:00 → MDW 2026-11-22 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2026-11-22 08:30:00 → LGB 2026-11-22 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2026-11-22 11:35:00 → MDW 2026-11-22 17:20:00.

2026-11-21 · one way · Axel-exclusive $175.00

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

2026-11-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN4605 / WN4990: OAK 2026-11-22 20:45:00 → MDW 2026-11-23 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2026-11-22 20:45:00 → LAS 2026-11-22 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2026-11-23 00:20:00 → MDW 2026-11-23 05:40:00.

2026-11-21 · one way · Axel-exclusive $175.00

• Southwest Airlines WN768 / WN2517: OAK 2026-11-21 15:40:00 → MDW 2026-11-22 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2026-11-21 15:40:00 → LAX 2026-11-21 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2026-11-21 18:45:00 → MDW 2026-11-22 00:40:00.

2026-11-20 · one way · Axel-exclusive $175.00

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

2026-11-20 · one way · Axel-exclusive $175.00

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

2026-11-22 · one way · Axel-exclusive $175.00

• Southwest Airlines WN768 / WN2517: OAK 2026-11-22 15:40:00 → MDW 2026-11-23 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2026-11-22 15:40:00 → LAX 2026-11-22 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2026-11-22 18:45:00 → MDW 2026-11-23 00:40:00.

2026-11-20 · one way · Axel-exclusive $175.00

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

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.

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