Oakland (OAK) to Chicago (MDW) · Jan 8, 2027 · return Jan 11, 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: San Francisco Bay Area to Chicago (MDW) flight deals

2027-01-08 → 2027-01-11 · Axel-exclusive $323.00

• Southwest Airlines WN4674 / WN4349: OAK 2027-01-08 07:45:00 → MDW 2027-01-08 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
  • WN4674: OAK 2027-01-08 07:45:00 → SLC 2027-01-08 10:25:00; layover at SLC: 205 minutes.
  • WN4349: SLC 2027-01-08 13:50:00 → MDW 2027-01-08 17:45:00.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-11 15:45:00 → OAK 2027-01-11 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-11 15:45:00 → LAX 2027-01-11 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-11 20:00:00 → OAK 2027-01-11 21:15:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $323.00

• Southwest Airlines WN3238 / WN2962: OAK 2027-01-08 13:35:00 → MDW 2027-01-08 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2027-01-08 13:35:00 → SAN 2027-01-08 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2027-01-08 16:05:00 → MDW 2027-01-08 22:00:00.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-11 15:45:00 → OAK 2027-01-11 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-11 15:45:00 → LAX 2027-01-11 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-11 20:00:00 → OAK 2027-01-11 21:15:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $323.00

• Southwest Airlines WN768 / WN2517: OAK 2027-01-08 15:40:00 → MDW 2027-01-09 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2027-01-08 15:40:00 → LAX 2027-01-08 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2027-01-08 18:45:00 → MDW 2027-01-09 00:40:00.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-11 15:45:00 → OAK 2027-01-11 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-11 15:45:00 → LAX 2027-01-11 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-11 20:00:00 → OAK 2027-01-11 21:15:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $323.00

• Southwest Airlines WN3217 / WN801: OAK 2027-01-08 08:30:00 → MDW 2027-01-08 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2027-01-08 08:30:00 → LGB 2027-01-08 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2027-01-08 11:35:00 → MDW 2027-01-08 17:20:00.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-11 15:45:00 → OAK 2027-01-11 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-11 15:45:00 → LAX 2027-01-11 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-11 20:00:00 → OAK 2027-01-11 21:15:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $323.00

• Southwest Airlines WN4605 / WN4990: OAK 2027-01-08 20:45:00 → MDW 2027-01-09 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2027-01-08 20:45:00 → LAS 2027-01-08 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2027-01-09 00:20:00 → MDW 2027-01-09 05:40:00.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-11 15:45:00 → OAK 2027-01-11 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-11 15:45:00 → LAX 2027-01-11 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-11 20:00:00 → OAK 2027-01-11 21:15:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-08 23:50:00 → MDW 2027-01-09 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-11 15:45:00 → OAK 2027-01-11 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-11 15:45:00 → LAX 2027-01-11 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-11 20:00:00 → OAK 2027-01-11 21:15:00.

Explore this route

• All dates for this route
• Jan 7, 2027 · Return options
• Jan 9, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Jan 8, 2027 · return Jan 11, 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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