Oakland (OAK) to Chicago (MDW) · Jan 7, 2027 · return Jan 17, 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

2027-01-07 → 2027-01-17 · Axel-exclusive $323.00

• Southwest Airlines WN4674 / WN4349: OAK 2027-01-07 07:45:00 → MDW 2027-01-07 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
  • WN4674: OAK 2027-01-07 07:45:00 → SLC 2027-01-07 10:25:00; layover at SLC: 205 minutes.
  • WN4349: SLC 2027-01-07 13:50:00 → MDW 2027-01-07 17:45:00.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

2027-01-07 → 2027-01-17 · Axel-exclusive $323.00

• Southwest Airlines WN3217 / WN801: OAK 2027-01-07 08:30:00 → MDW 2027-01-07 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2027-01-07 08:30:00 → LGB 2027-01-07 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2027-01-07 11:35:00 → MDW 2027-01-07 17:20:00.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

2027-01-07 → 2027-01-17 · Axel-exclusive $323.00

• Southwest Airlines WN3238 / WN2962: OAK 2027-01-07 13:35:00 → MDW 2027-01-07 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2027-01-07 13:35:00 → SAN 2027-01-07 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2027-01-07 16:05:00 → MDW 2027-01-07 22:00:00.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

2027-01-07 → 2027-01-17 · Axel-exclusive $323.00

• Southwest Airlines WN768 / WN2517: OAK 2027-01-07 15:40:00 → MDW 2027-01-08 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2027-01-07 15:40:00 → LAX 2027-01-07 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2027-01-07 18:45:00 → MDW 2027-01-08 00:40:00.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

2027-01-07 → 2027-01-17 · Axel-exclusive $323.00

• Southwest Airlines WN4605 / WN4990: OAK 2027-01-07 20:45:00 → MDW 2027-01-08 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2027-01-07 20:45:00 → LAS 2027-01-07 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2027-01-08 00:20:00 → MDW 2027-01-08 05:40:00.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

2027-01-07 → 2027-01-17 · Axel-exclusive $332.50

• Southwest Airlines WN1082: OAK 2027-01-07 05:50:00 → MDW 2027-01-07 11:50:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

Explore this route

• All dates for this route
• Jan 6, 2027 · Return options
• Jan 8, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Jan 7, 2027 · return Jan 17, 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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