Oakland (OAK) to Chicago (MDW) · Nov 25, 2026 · return Dec 5, 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: San Francisco Bay Area to Chicago (MDW) flight deals

2026-11-25 → 2026-12-05 · Axel-exclusive $432.00

• Southwest Airlines WN3220: OAK 2026-11-25 23:50:00 → MDW 2026-11-26 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $432.00

• Southwest Airlines WN2871: OAK 2026-11-25 06:30:00 → MDW 2026-11-25 12:30:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $418.00

• Southwest Airlines WN3203 / WN776: OAK 2026-11-25 11:25:00 → MDW 2026-11-25 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2026-11-25 11:25:00 → DEN 2026-11-25 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2026-11-25 18:05:00 → MDW 2026-11-25 21:30:00.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $418.00

• Southwest Airlines WN4674 / WN4349: OAK 2026-11-25 07:45:00 → MDW 2026-11-25 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
  • WN4674: OAK 2026-11-25 07:45:00 → SLC 2026-11-25 10:25:00; layover at SLC: 205 minutes.
  • WN4349: SLC 2026-11-25 13:50:00 → MDW 2026-11-25 17:45:00.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $418.00

• Southwest Airlines WN3217 / WN801: OAK 2026-11-25 08:30:00 → MDW 2026-11-25 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2026-11-25 08:30:00 → LGB 2026-11-25 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2026-11-25 11:35:00 → MDW 2026-11-25 17:20:00.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $418.00

• Southwest Airlines WN3238 / WN2962: OAK 2026-11-25 13:35:00 → MDW 2026-11-25 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2026-11-25 13:35:00 → SAN 2026-11-25 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2026-11-25 16:05:00 → MDW 2026-11-25 22:00:00.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $418.00

• Southwest Airlines WN4605 / WN4990: OAK 2026-11-25 20:45:00 → MDW 2026-11-26 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2026-11-25 20:45:00 → LAS 2026-11-25 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2026-11-26 00:20:00 → MDW 2026-11-26 05:40:00.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

2026-11-25 → 2026-12-05 · Axel-exclusive $418.00

• Southwest Airlines WN768 / WN2517: OAK 2026-11-25 15:40:00 → MDW 2026-11-26 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2026-11-25 15:40:00 → LAX 2026-11-25 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2026-11-25 18:45:00 → MDW 2026-11-26 00:40:00.
• Southwest Airlines WN2990: MDW 2026-12-05 21:30:00 → OAK 2026-12-06 00:15:00; nonstop; 285 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 24, 2026 · Return options
• Nov 26, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Nov 25, 2026 · return Dec 5, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Francisco Bay Area to Chicago (MDW) flight deals · Flight search guide.
• 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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