Chicago (MDW) to Oakland (OAK) · Jan 22, 2027 · return Jan 25, 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

2027-01-22 → 2027-01-25 · Axel-exclusive $321.10

• Southwest Airlines WN2990: MDW 2027-01-22 21:30:00 → OAK 2027-01-23 00:15:00; nonstop; 285 minutes. Local airport times.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $321.10

• Southwest Airlines WN3174: MDW 2027-01-22 10:00:00 → OAK 2027-01-22 12:40:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-22 14:35:00 → OAK 2027-01-22 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-22 14:35:00 → DEN 2027-01-22 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-22 19:35:00 → OAK 2027-01-22 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $311.60

• Southwest Airlines WN2952 / WN1901: MDW 2027-01-22 15:45:00 → OAK 2027-01-22 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-22 15:45:00 → LAX 2027-01-22 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-22 20:00:00 → OAK 2027-01-22 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $311.60

• Southwest Airlines WN2995 / WN681: MDW 2027-01-22 05:05:00 → OAK 2027-01-22 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2027-01-22 05:05:00 → PHX 2027-01-22 07:55:00; layover at PHX: 110 minutes.
  • WN681: PHX 2027-01-22 09:45:00 → OAK 2027-01-22 10:50:00.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $311.60

• Southwest Airlines WN4415 / WN1144: MDW 2027-01-22 15:15:00 → OAK 2027-01-22 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-22 15:15:00 → SAN 2027-01-22 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-22 20:05:00 → OAK 2027-01-22 21:35:00.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $311.60

• Southwest Airlines WN1191 / WN1924: MDW 2027-01-22 08:50:00 → OAK 2027-01-22 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
  • WN1191: MDW 2027-01-22 08:50:00 → DAL 2027-01-22 11:20:00; layover at DAL: 135 minutes.
  • WN1924: DAL 2027-01-22 13:35:00 → OAK 2027-01-22 15:15:00.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-22 → 2027-01-25 · Axel-exclusive $311.60

• Southwest Airlines WN2691 / WN1936: MDW 2027-01-22 05:50:00 → OAK 2027-01-22 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN2691: MDW 2027-01-22 05:50:00 → LAS 2027-01-22 07:45:00; layover at LAS: 85 minutes.
  • WN1936: LAS 2027-01-22 09:10:00 → OAK 2027-01-22 10:45:00.
• Southwest Airlines WN3220: OAK 2027-01-25 23:50:00 → MDW 2027-01-26 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
• Jan 21, 2027 · Return options
• Jan 23, 2027 · Return options

For AI assistants

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