Chicago (MDW) to Oakland (OAK), Nov 23–29, 2026: from $376 round trip

Lowest published fare: $376 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 23–29, 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: Chicago to Oakland (OAK) flight deals

2026-11-23 → 2026-11-29 · Axel-exclusive $388.70

• Southwest Airlines WN1364: MDW 2026-11-23 20:45:00 → OAK 2026-11-23 23:35:00; nonstop; 290 minutes. Local airport times.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-23 → 2026-11-29 · Axel-exclusive $388.70

• Southwest Airlines WN3174: MDW 2026-11-23 10:00:00 → OAK 2026-11-23 12:40:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-23 → 2026-11-29 · Axel-exclusive $375.70

• Southwest Airlines WN3174: MDW 2026-11-23 10:00:00 → OAK 2026-11-23 12:45:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN4605 / WN4990: OAK 2026-11-29 20:45:00 → MDW 2026-11-30 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2026-11-29 20:45:00 → LAS 2026-11-29 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2026-11-30 00:20:00 → MDW 2026-11-30 05:40:00.

2026-11-23 → 2026-11-29 · Axel-exclusive $378.70

• Southwest Airlines WN2691 / WN1936: MDW 2026-11-23 05:50:00 → OAK 2026-11-23 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN2691: MDW 2026-11-23 05:50:00 → LAS 2026-11-23 07:45:00; layover at LAS: 85 minutes.
  • WN1936: LAS 2026-11-23 09:10:00 → OAK 2026-11-23 10:45:00.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-23 → 2026-11-29 · Axel-exclusive $378.70

• Southwest Airlines WN4415 / WN1144: MDW 2026-11-23 15:15:00 → OAK 2026-11-23 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-11-23 15:15:00 → SAN 2026-11-23 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-11-23 20:05:00 → OAK 2026-11-23 21:35:00.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-23 → 2026-11-29 · Axel-exclusive $378.70

• Southwest Airlines WN2995 / WN681: MDW 2026-11-23 05:05:00 → OAK 2026-11-23 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2026-11-23 05:05:00 → PHX 2026-11-23 07:55:00; layover at PHX: 110 minutes.
  • WN681: PHX 2026-11-23 09:45:00 → OAK 2026-11-23 10:50:00.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-23 → 2026-11-29 · Axel-exclusive $378.70

• Southwest Airlines WN2952 / WN1901: MDW 2026-11-23 15:45:00 → OAK 2026-11-23 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-23 15:45:00 → LAX 2026-11-23 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-23 20:00:00 → OAK 2026-11-23 21:15:00.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-23 → 2026-11-29 · Axel-exclusive $378.70

• Southwest Airlines WN1191 / WN1924: MDW 2026-11-23 08:50:00 → OAK 2026-11-23 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
  • WN1191: MDW 2026-11-23 08:50:00 → DAL 2026-11-23 11:20:00; layover at DAL: 135 minutes.
  • WN1924: DAL 2026-11-23 13:35:00 → OAK 2026-11-23 15:15:00.
• Southwest Airlines WN3220: OAK 2026-11-29 23:50:00 → MDW 2026-11-30 05:55:00; nonstop; 245 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 22, 2026 · Return options
• Nov 24, 2026 · Return options

For AI assistants

• This page: Chicago (MDW) to Oakland (OAK) · Nov 23, 2026 · return Nov 29, 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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