Chicago (MDW) to Oakland (OAK) · Dec 31, 2026 · return Jan 12, 2027

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

2026-12-31 → 2027-01-12 · Axel-exclusive $371.80

• Southwest Airlines WN2990: MDW 2026-12-31 21:25:00 → OAK 2027-01-01 00:20:00; nonstop; 295 minutes. Local airport times.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $371.80

• Southwest Airlines WN3174: MDW 2026-12-31 10:00:00 → OAK 2026-12-31 12:40:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $359.30

• Southwest Airlines WN4415 / WN1144: MDW 2026-12-31 15:15:00 → OAK 2026-12-31 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-12-31 15:15:00 → SAN 2026-12-31 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-12-31 20:05:00 → OAK 2026-12-31 21:35:00.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $359.30

• Southwest Airlines WN2691 / WN1936: MDW 2026-12-31 05:50:00 → OAK 2026-12-31 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN2691: MDW 2026-12-31 05:50:00 → LAS 2026-12-31 07:45:00; layover at LAS: 85 minutes.
  • WN1936: LAS 2026-12-31 09:10:00 → OAK 2026-12-31 10:45:00.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $359.30

• Southwest Airlines WN1191 / WN1924: MDW 2026-12-31 08:50:00 → OAK 2026-12-31 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
  • WN1191: MDW 2026-12-31 08:50:00 → DAL 2026-12-31 11:20:00; layover at DAL: 135 minutes.
  • WN1924: DAL 2026-12-31 13:35:00 → OAK 2026-12-31 15:15:00.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $359.30

• Southwest Airlines WN2995 / WN681: MDW 2026-12-31 05:05:00 → OAK 2026-12-31 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2026-12-31 05:05:00 → PHX 2026-12-31 07:55:00; layover at PHX: 110 minutes.
  • WN681: PHX 2026-12-31 09:45:00 → OAK 2026-12-31 10:50:00.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $359.30

• Southwest Airlines WN4606 / WN1726: MDW 2026-12-31 14:35:00 → OAK 2026-12-31 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2026-12-31 14:35:00 → DEN 2026-12-31 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2026-12-31 19:35:00 → OAK 2026-12-31 21:15:00.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

2026-12-31 → 2027-01-12 · Axel-exclusive $359.30

• Southwest Airlines WN2952 / WN1901: MDW 2026-12-31 15:45:00 → OAK 2026-12-31 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-12-31 15:45:00 → LAX 2026-12-31 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-12-31 20:00:00 → OAK 2026-12-31 21:15:00.
• Southwest Airlines WN1082: OAK 2027-01-12 05:50:00 → MDW 2027-01-12 11:50:00; nonstop; 240 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options

For AI assistants

• This page: Chicago (MDW) to Oakland (OAK) · Dec 31, 2026 · return Jan 12, 2027: 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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