Chicago (MDW) to Oakland (OAK) · Jan 8, 2027 · one way

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

2027-01-08 · one way · Axel-exclusive $170.05

• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-08 · one way · Axel-exclusive $170.05

• Southwest Airlines WN3174: MDW 2027-01-08 10:00:00 → OAK 2027-01-08 12:40:00; nonstop; 280 minutes. Local airport times.

2027-01-08 · one way · Axel-exclusive $160.55

• Southwest Airlines WN2995 / WN681: MDW 2027-01-08 05:05:00 → OAK 2027-01-08 10:50:00; 1 stop(s) via PHX; 465 minutes. Local airport times.
  • WN2995: MDW 2027-01-08 05:05:00 → PHX 2027-01-08 07:55:00; layover at PHX: 110 minutes.
  • WN681: PHX 2027-01-08 09:45:00 → OAK 2027-01-08 10:50:00.

2027-01-08 · one way · Axel-exclusive $160.55

• Southwest Airlines WN2691 / WN1936: MDW 2027-01-08 05:50:00 → OAK 2027-01-08 10:45:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN2691: MDW 2027-01-08 05:50:00 → LAS 2027-01-08 07:45:00; layover at LAS: 85 minutes.
  • WN1936: LAS 2027-01-08 09:10:00 → OAK 2027-01-08 10:45:00.

2027-01-08 · one way · Axel-exclusive $160.55

• Southwest Airlines WN1191 / WN1924: MDW 2027-01-08 08:50:00 → OAK 2027-01-08 15:15:00; 1 stop(s) via DAL; 505 minutes. Local airport times.
  • WN1191: MDW 2027-01-08 08:50:00 → DAL 2027-01-08 11:20:00; layover at DAL: 135 minutes.
  • WN1924: DAL 2027-01-08 13:35:00 → OAK 2027-01-08 15:15:00.

2027-01-08 · one way · Axel-exclusive $160.55

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

2027-01-08 · one way · Axel-exclusive $160.55

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

2027-01-08 · one way · Axel-exclusive $160.55

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

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Jan 7, 2027 · Return options
• Jan 9, 2027 · Return options

For AI assistants

• This page: Chicago (MDW) to Oakland (OAK) · Jan 8, 2027 · one way: 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 Chicago to Oakland (OAK) 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.

Feedback (optional): Missing info · Axel issue