Oakland (OAK) to Chicago (MDW) · Jan 5, 2027 · return Jan 8, 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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Jan 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $276 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $325 total · 5★ Nobu Hotel Chicago, $1,069 total

All hotels in Chicago

Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

2027-01-05 → 2027-01-08 · Axel-exclusive $342.00

• Southwest Airlines WN1082: OAK 2027-01-05 05:50:00 → MDW 2027-01-05 11:50:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-05 23:50:00 → MDW 2027-01-06 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $332.50

• Southwest Airlines WN3217 / WN801: OAK 2027-01-05 08:30:00 → MDW 2027-01-05 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
  • WN3217: OAK 2027-01-05 08:30:00 → LGB 2027-01-05 10:00:00; layover at LGB: 95 minutes.
  • WN801: LGB 2027-01-05 11:35:00 → MDW 2027-01-05 17:20:00.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $332.50

• Southwest Airlines WN4605 / WN4990: OAK 2027-01-05 20:45:00 → MDW 2027-01-06 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
  • WN4605: OAK 2027-01-05 20:45:00 → LAS 2027-01-05 22:15:00; layover at LAS: 125 minutes.
  • WN4990: LAS 2027-01-06 00:20:00 → MDW 2027-01-06 05:40:00.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $332.50

• Southwest Airlines WN3203 / WN776: OAK 2027-01-05 11:25:00 → MDW 2027-01-05 21:30:00; 1 stop(s) via DEN; 485 minutes. Local airport times.
  • WN3203: OAK 2027-01-05 11:25:00 → DEN 2027-01-05 14:50:00; layover at DEN: 195 minutes.
  • WN776: DEN 2027-01-05 18:05:00 → MDW 2027-01-05 21:30:00.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $332.50

• Southwest Airlines WN768 / WN2517: OAK 2027-01-05 15:40:00 → MDW 2027-01-06 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
  • WN768: OAK 2027-01-05 15:40:00 → LAX 2027-01-05 17:05:00; layover at LAX: 100 minutes.
  • WN2517: LAX 2027-01-05 18:45:00 → MDW 2027-01-06 00:40:00.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $332.50

• Southwest Airlines WN3238 / WN2962: OAK 2027-01-05 13:35:00 → MDW 2027-01-05 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
  • WN3238: OAK 2027-01-05 13:35:00 → SAN 2027-01-05 15:05:00; layover at SAN: 60 minutes.
  • WN2962: SAN 2027-01-05 16:05:00 → MDW 2027-01-05 22:00:00.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-05 → 2027-01-08 · Axel-exclusive $332.50

• Southwest Airlines WN4674 / WN4349: OAK 2027-01-05 07:45:00 → MDW 2027-01-05 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
  • WN4674: OAK 2027-01-05 07:45:00 → SLC 2027-01-05 10:25:00; layover at SLC: 205 minutes.
  • WN4349: SLC 2027-01-05 13:50:00 → MDW 2027-01-05 17:45:00.
• Southwest Airlines WN2990: MDW 2027-01-08 21:30:00 → OAK 2027-01-09 00:15:00; nonstop; 285 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 4, 2027 · Return options
• Jan 6, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Jan 5, 2027 · return Jan 8, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• 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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