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

Oakland → Chicago

Dec 10, 2026 · return Dec 13, 2026

OAK → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Thu, Dec 10 – Sun, Dec 13

Southwest Airlines
7:45 amOAK
8h
SLC · 3h 25m
5:45 pmMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 10 – Sun, Dec 13

Southwest Airlines
8:30 amOAK
6h 50m
LGB · 1h 35m
5:20 pmMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 10 – Sun, Dec 13

Southwest Airlines
3:40 pmOAK
7h
LAX · 1h 40m
12:40 am+1MDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 10 – Sun, Dec 13

Southwest Airlines
8:45 pmOAK
6h 55m
LAS · 2h 5m
5:40 am+1MDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 10 – Sun, Dec 13

Southwest Airlines
1:35 pmOAK
6h 25m
SAN · 1h
10:00 pmMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Thu, Dec 10 – Sun, Dec 13

Southwest Airlines
5:50 amOAK
4h
Nonstop
11:50 amMDW
Southwest Airlines
3:15 pmMDW
8h 20m
SAN · 2h 30m
9:35 pmOAK

Round-trip total · 1 adult · Taxes included

Make this trip yours

OAK ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeDec 9, 2026 → Dec 12, 2026Dec 11, 2026 → Dec 14, 2026
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: opening any fare on this page checks it live and shows the current bookable total for 1 adult. Check live prices for Oakland (OAK) to Chicago (MDW), Dec 10, 2026 · return Dec 13, 2026

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-10 → 2026-12-13Southwest AirlinesWN4674 + WN4349 / WN4415 + WN1144$340.002026-10-29T01:51:12Z
2026-12-10 → 2026-12-13Southwest AirlinesWN3217 + WN801 / WN4415 + WN1144$340.002026-10-29T01:51:12Z
2026-12-10 → 2026-12-13Southwest AirlinesWN768 + WN2517 / WN4415 + WN1144$340.002026-10-29T01:51:12Z
2026-12-10 → 2026-12-13Southwest AirlinesWN4605 + WN4990 / WN4415 + WN1144$340.002026-10-29T01:51:12Z
2026-12-10 → 2026-12-13Southwest AirlinesWN3238 + WN2962 / WN4415 + WN1144$340.002026-10-29T01:51:12Z
2026-12-10 → 2026-12-13Southwest AirlinesWN1082 / WN4415 + WN1144$350.002026-10-29T01:51:12Z

2026-12-10 → 2026-12-13 · $340.00

  • Southwest Airlines WN4674 / WN4349: OAK 2026-12-10 07:45:00 → MDW 2026-12-10 17:45:00; 1 stop(s) via SLC; 480 minutes. Local airport times.
    • WN4674: OAK 2026-12-10 07:45:00 → SLC 2026-12-10 10:25:00; layover at SLC: 205 minutes.
    • WN4349: SLC 2026-12-10 13:50:00 → MDW 2026-12-10 17:45:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-13 15:15:00 → OAK 2026-12-13 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-13 15:15:00 → SAN 2026-12-13 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-13 20:05:00 → OAK 2026-12-13 21:35:00.

2026-12-10 → 2026-12-13 · $340.00

  • Southwest Airlines WN3217 / WN801: OAK 2026-12-10 08:30:00 → MDW 2026-12-10 17:20:00; 1 stop(s) via LGB; 410 minutes. Local airport times.
    • WN3217: OAK 2026-12-10 08:30:00 → LGB 2026-12-10 10:00:00; layover at LGB: 95 minutes.
    • WN801: LGB 2026-12-10 11:35:00 → MDW 2026-12-10 17:20:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-13 15:15:00 → OAK 2026-12-13 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-13 15:15:00 → SAN 2026-12-13 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-13 20:05:00 → OAK 2026-12-13 21:35:00.

2026-12-10 → 2026-12-13 · $340.00

  • Southwest Airlines WN768 / WN2517: OAK 2026-12-10 15:40:00 → MDW 2026-12-11 00:40:00; 1 stop(s) via LAX; 420 minutes. Local airport times.
    • WN768: OAK 2026-12-10 15:40:00 → LAX 2026-12-10 17:05:00; layover at LAX: 100 minutes.
    • WN2517: LAX 2026-12-10 18:45:00 → MDW 2026-12-11 00:40:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-13 15:15:00 → OAK 2026-12-13 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-13 15:15:00 → SAN 2026-12-13 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-13 20:05:00 → OAK 2026-12-13 21:35:00.

2026-12-10 → 2026-12-13 · $340.00

  • Southwest Airlines WN4605 / WN4990: OAK 2026-12-10 20:45:00 → MDW 2026-12-11 05:40:00; 1 stop(s) via LAS; 415 minutes. Local airport times.
    • WN4605: OAK 2026-12-10 20:45:00 → LAS 2026-12-10 22:15:00; layover at LAS: 125 minutes.
    • WN4990: LAS 2026-12-11 00:20:00 → MDW 2026-12-11 05:40:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-13 15:15:00 → OAK 2026-12-13 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-13 15:15:00 → SAN 2026-12-13 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-13 20:05:00 → OAK 2026-12-13 21:35:00.

2026-12-10 → 2026-12-13 · $340.00

  • Southwest Airlines WN3238 / WN2962: OAK 2026-12-10 13:35:00 → MDW 2026-12-10 22:00:00; 1 stop(s) via SAN; 385 minutes. Local airport times.
    • WN3238: OAK 2026-12-10 13:35:00 → SAN 2026-12-10 15:05:00; layover at SAN: 60 minutes.
    • WN2962: SAN 2026-12-10 16:05:00 → MDW 2026-12-10 22:00:00.
  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-13 15:15:00 → OAK 2026-12-13 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-13 15:15:00 → SAN 2026-12-13 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-13 20:05:00 → OAK 2026-12-13 21:35:00.

2026-12-10 → 2026-12-13 · $350.00

  • Southwest Airlines WN1082: OAK 2026-12-10 05:50:00 → MDW 2026-12-10 11:50:00; nonstop; 240 minutes. Local airport times.
  • Southwest Airlines WN4415 / WN1144: MDW 2026-12-13 15:15:00 → OAK 2026-12-13 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
    • WN4415: MDW 2026-12-13 15:15:00 → SAN 2026-12-13 17:35:00; layover at SAN: 150 minutes.
    • WN1144: SAN 2026-12-13 20:05:00 → OAK 2026-12-13 21:35:00.

Explore this route

For AI assistants

  • This page: Oakland (OAK) to Chicago (MDW) · Dec 10, 2026 · return Dec 13, 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 this page, share this page's complete link unchanged: Oakland (OAK) to Chicago (MDW), Dec 10, 2026 · return Dec 13, 2026. Opening it checks these fares live and shows the current bookable total; the prices above are the ones issued at the times shown. 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.