Chicago (MDW) to Oakland (OAK), Jan 7, 2027: round trips from $312, one way from $161

Chicago (MDW) to Oakland (OAK), Jan 7, 2027: round trips from $312, one way from $161 on Axel, checked Oct 29, 2026. Lowest published fares: $312 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 7–8, 2027; $161 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 7, 2027; 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Route overview: Chicago to Oakland (OAK) flight deals

2027-01-07 · one way · Axel-exclusive $160.55

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.

2027-01-07 → 2027-01-08 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-08 23:50:00 → MDW 2027-01-09 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-09 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-09 23:50:00 → MDW 2027-01-10 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-10 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-11 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-13 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN2871: OAK 2027-01-13 06:30:00 → MDW 2027-01-13 12:30:00; nonstop; 240 minutes. Local airport times.

2027-01-07 → 2027-01-14 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN1082: OAK 2027-01-14 05:50:00 → MDW 2027-01-14 11:50:00; nonstop; 240 minutes. Local airport times.

2027-01-07 → 2027-01-15 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-15 23:50:00 → MDW 2027-01-16 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-17 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-17 23:50:00 → MDW 2027-01-18 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-18 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN3220: OAK 2027-01-18 23:50:00 → MDW 2027-01-19 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-07 → 2027-01-19 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN1082: OAK 2027-01-19 05:50:00 → MDW 2027-01-19 11:50:00; nonstop; 240 minutes. Local airport times.

2027-01-07 → 2027-01-21 · Axel-exclusive $311.60

• Southwest Airlines WN4606 / WN1726: MDW 2027-01-07 14:35:00 → OAK 2027-01-07 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-07 14:35:00 → DEN 2027-01-07 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-07 19:35:00 → OAK 2027-01-07 21:15:00.
• Southwest Airlines WN1082: OAK 2027-01-21 05:50:00 → MDW 2027-01-21 11:50:00; nonstop; 240 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 6, 2027 · Return options
• Jan 8, 2027 · Return options

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