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Route overview: Chicago to San Francisco (SFO) flight deals

Chicago → San Francisco

Dec 4, 2026 · return Dec 12, 2026

MDW → SFO1 adulteconomyRound trip

6 flight options · 2 airlines

One-stop flights

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
10:00 amMDW
7h 45m
LAS · 2h 5m
3:45 pmSFO
Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Dec 4 – Sat, Dec 12

Delta Air Lines
1:31 pmMDW
7h 45m
DTW · 1h 15m
7:16 pmSFO
Delta Air Lines
6:00 amSFO
8h 18m
ATL · 1h 56m
4:18 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
9:55 amMDW
7h 55m
BNA · 1h 20m
3:50 pmSFO
Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
6:05 pmMDW
7h 50m
PHX · 1h 45m
11:55 pmSFO
Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
2:35 pmMDW
6h 45m
DEN · 1h 20m
7:20 pmSFO
Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW

Round-trip total · 1 adult · Taxes included

Fri, Dec 4 – Sat, Dec 12

Southwest Airlines
9:55 amMDW
4h 50m
Nonstop
12:45 pmSFO
Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SFO

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 3, 2026 → Dec 11, 2026Dec 5, 2026 → Dec 13, 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: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Chicago to San Francisco (SFO) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-04 → 2026-12-12Southwest AirlinesWN142 + WN2440 / WN2749 + WN4963$300.002026-10-29T01:29:13Z
2026-12-04 → 2026-12-12Delta Air LinesDL4688 + DL442 / DL570 + DL1728$350.002026-10-29T01:29:13Z
2026-12-04 → 2026-12-12Southwest AirlinesWN725 + WN4254 / WN2749 + WN4963$300.002026-10-29T01:29:13Z
2026-12-04 → 2026-12-12Southwest AirlinesWN2998 + WN1448 / WN2749 + WN4963$300.002026-10-29T01:29:13Z
2026-12-04 → 2026-12-12Southwest AirlinesWN4606 + WN1817 / WN2749 + WN4963$300.002026-10-29T01:29:13Z
2026-12-04 → 2026-12-12Southwest AirlinesWN786 / WN2749 + WN4963$315.002026-10-29T01:29:13Z

2026-12-04 → 2026-12-12 · $300.00

  • Southwest Airlines WN142 / WN2440: MDW 2026-12-04 10:00:00 → SFO 2026-12-04 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
    • WN142: MDW 2026-12-04 10:00:00 → LAS 2026-12-04 11:55:00; layover at LAS: 125 minutes.
    • WN2440: LAS 2026-12-04 14:00:00 → SFO 2026-12-04 15:45:00.
  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.

2026-12-04 → 2026-12-12 · $350.00

  • Delta Air Lines DL4688 / DL442: MDW 2026-12-04 13:31:00 → SFO 2026-12-04 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-04 16:59:00 → SFO 2026-12-04 19:16:00.
  • Delta Air Lines DL570 / DL1728: SFO 2026-12-12 06:00:00 → MDW 2026-12-12 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-12 06:00:00 → ATL 2026-12-12 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-12 15:25:00 → MDW 2026-12-12 16:18:00.

2026-12-04 → 2026-12-12 · $300.00

  • Southwest Airlines WN725 / WN4254: MDW 2026-12-04 09:55:00 → SFO 2026-12-04 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
    • WN725: MDW 2026-12-04 09:55:00 → BNA 2026-12-04 11:30:00; layover at BNA: 80 minutes.
    • WN4254: BNA 2026-12-04 12:50:00 → SFO 2026-12-04 15:50:00.
  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.

2026-12-04 → 2026-12-12 · $300.00

  • Southwest Airlines WN2998 / WN1448: MDW 2026-12-04 18:05:00 → SFO 2026-12-04 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
    • WN2998: MDW 2026-12-04 18:05:00 → PHX 2026-12-04 21:00:00; layover at PHX: 105 minutes.
    • WN1448: PHX 2026-12-04 22:45:00 → SFO 2026-12-04 23:55:00.
  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.

2026-12-04 → 2026-12-12 · $300.00

  • Southwest Airlines WN4606 / WN1817: MDW 2026-12-04 14:35:00 → SFO 2026-12-04 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
    • WN4606: MDW 2026-12-04 14:35:00 → DEN 2026-12-04 16:15:00; layover at DEN: 80 minutes.
    • WN1817: DEN 2026-12-04 17:35:00 → SFO 2026-12-04 19:20:00.
  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.

2026-12-04 → 2026-12-12 · $315.00

  • Southwest Airlines WN786: MDW 2026-12-04 09:55:00 → SFO 2026-12-04 12:45:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-12 20:20:00 → MDW 2026-12-13 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-12 20:20:00 → PHX 2026-12-12 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-13 01:35:00 → MDW 2026-12-13 05:45:00.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to San Francisco (SFO) · Dec 4, 2026 · return Dec 12, 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 Chicago to San Francisco (SFO) 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.