Chicago (MDW) to Oakland (OAK) · Nov 27, 2026 · return Dec 3, 2026

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

2026-11-27 → 2026-12-03 · Axel-exclusive $388.70

• Southwest Airlines WN1364: MDW 2026-11-27 20:45:00 → OAK 2026-11-27 23:35:00; nonstop; 290 minutes. Local airport times.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $388.70

• Southwest Airlines WN3174: MDW 2026-11-27 10:00:00 → OAK 2026-11-27 12:40:00; nonstop; 280 minutes. Local airport times.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $375.70

• Southwest Airlines WN4606 / WN1726: MDW 2026-11-27 14:35:00 → OAK 2026-11-27 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2026-11-27 14:35:00 → DEN 2026-11-27 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2026-11-27 19:35:00 → OAK 2026-11-27 21:15:00.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $375.70

• Southwest Airlines WN2952 / WN1901: MDW 2026-11-27 15:45:00 → OAK 2026-11-27 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2026-11-27 15:45:00 → LAX 2026-11-27 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2026-11-27 20:00:00 → OAK 2026-11-27 21:15:00.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $375.70

• Southwest Airlines WN1191 / WN1924: MDW 2026-11-27 08:50:00 → OAK 2026-11-27 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
  • WN1191: MDW 2026-11-27 08:50:00 → DAL 2026-11-27 11:20:00; layover at DAL: 135 minutes.
  • WN1924: DAL 2026-11-27 13:35:00 → OAK 2026-11-27 15:15:00.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $375.70

• Southwest Airlines WN2995 / WN681: MDW 2026-11-27 05:05:00 → OAK 2026-11-27 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2026-11-27 05:05:00 → PHX 2026-11-27 07:55:00; layover at PHX: 110 minutes.
  • WN681: PHX 2026-11-27 09:45:00 → OAK 2026-11-27 10:50:00.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $375.70

• Southwest Airlines WN2691 / WN1936: MDW 2026-11-27 05:50:00 → OAK 2026-11-27 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN2691: MDW 2026-11-27 05:50:00 → LAS 2026-11-27 07:45:00; layover at LAS: 85 minutes.
  • WN1936: LAS 2026-11-27 09:10:00 → OAK 2026-11-27 10:45:00.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $375.70

• Southwest Airlines WN4415 / WN1144: MDW 2026-11-27 15:15:00 → OAK 2026-11-27 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2026-11-27 15:15:00 → SAN 2026-11-27 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2026-11-27 20:05:00 → OAK 2026-11-27 21:35:00.
• Southwest Airlines WN3220: OAK 2026-12-03 23:50:00 → MDW 2026-12-04 05:55:00; nonstop; 245 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 26, 2026 · Return options
• Nov 28, 2026 · Return options

For AI assistants

• This page: Chicago (MDW) to Oakland (OAK) · Nov 27, 2026 · return Dec 3, 2026: 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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