San Francisco (SFO) to Chicago (MDW) · Nov 18, 2026 · return Nov 22, 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

2026-11-18 → 2026-11-22 · Axel-exclusive $411.25

• Southwest Airlines WN3849: SFO 2026-11-18 23:35:00 → MDW 2026-11-19 06:00:00; nonstop; 265 minutes. Local airport times.
• Southwest Airlines WN4836: MDW 2026-11-22 21:30:00 → SFO 2026-11-23 00:25:00; nonstop; 295 minutes. Local airport times.

2026-11-18 → 2026-11-22 · Axel-exclusive $458.25

• Delta Air Lines DL570 / DL1728: SFO 2026-11-18 06:00:00 → MDW 2026-11-18 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
  • DL570: SFO 2026-11-18 06:00:00 → ATL 2026-11-18 13:29:00; layover at ATL: 116 minutes.
  • DL1728: ATL 2026-11-18 15:25:00 → MDW 2026-11-18 16:18:00.
• Delta Air Lines DL4688 / DL442: MDW 2026-11-22 13:31:00 → SFO 2026-11-22 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 75 minutes.
  • DL442: DTW 2026-11-22 16:59:00 → SFO 2026-11-22 19:16:00.

2026-11-18 → 2026-11-22 · Axel-exclusive $411.25

• Southwest Airlines WN2331: SFO 2026-11-18 06:00:00 → MDW 2026-11-18 12:15:00; nonstop; 255 minutes. Local airport times.
• Southwest Airlines WN4836: MDW 2026-11-22 21:30:00 → SFO 2026-11-23 00:25:00; nonstop; 295 minutes. Local airport times.

2026-11-18 → 2026-11-22 · Axel-exclusive $391.25

• Southwest Airlines WN3847 / WN2515: SFO 2026-11-18 08:20:00 → MDW 2026-11-18 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
  • WN3847: SFO 2026-11-18 08:20:00 → LAX 2026-11-18 09:50:00; layover at LAX: 85 minutes.
  • WN2515: LAX 2026-11-18 11:15:00 → MDW 2026-11-18 17:15:00.
• Southwest Airlines WN4836: MDW 2026-11-22 21:30:00 → SFO 2026-11-23 00:25:00; nonstop; 295 minutes. Local airport times.

2026-11-18 → 2026-11-22 · Axel-exclusive $391.25

• Southwest Airlines WN3428 / WN1699: SFO 2026-11-18 08:00:00 → MDW 2026-11-18 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
  • WN3428: SFO 2026-11-18 08:00:00 → DEN 2026-11-18 11:30:00; layover at DEN: 190 minutes.
  • WN1699: DEN 2026-11-18 14:40:00 → MDW 2026-11-18 17:55:00.
• Southwest Airlines WN4836: MDW 2026-11-22 21:30:00 → SFO 2026-11-23 00:25:00; nonstop; 295 minutes. Local airport times.

2026-11-18 → 2026-11-22 · Axel-exclusive $391.25

• Southwest Airlines WN2989 / WN4770: SFO 2026-11-18 13:05:00 → MDW 2026-11-18 23:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
  • WN2989: SFO 2026-11-18 13:05:00 → STL 2026-11-18 18:55:00; layover at STL: 175 minutes.
  • WN4770: STL 2026-11-18 21:50:00 → MDW 2026-11-18 23:00:00.
• Southwest Airlines WN4836: MDW 2026-11-22 21:30:00 → SFO 2026-11-23 00:25:00; nonstop; 295 minutes. Local airport times.

2026-11-18 → 2026-11-22 · Axel-exclusive $391.25

• Southwest Airlines WN2749 / WN4963: SFO 2026-11-18 20:20:00 → MDW 2026-11-19 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
  • WN2749: SFO 2026-11-18 20:20:00 → PHX 2026-11-18 23:35:00; layover at PHX: 120 minutes.
  • WN4963: PHX 2026-11-19 01:35:00 → MDW 2026-11-19 05:45:00.
• Southwest Airlines WN4836: MDW 2026-11-22 21:30:00 → SFO 2026-11-23 00:25:00; nonstop; 295 minutes. Local airport times.

2026-11-18 → 2026-11-22 · Axel-exclusive $458.25

• Delta Air Lines DL2178 / DL4714: SFO 2026-11-18 06:00:00 → MDW 2026-11-18 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
  • DL2178: SFO 2026-11-18 06:00:00 → MSP 2026-11-18 11:40:00; layover at MSP: 200 minutes.
  • DL4714: MSP 2026-11-18 15:00:00 → MDW 2026-11-18 16:39:00.
• Delta Air Lines DL4688 / DL442: MDW 2026-11-22 13:31:00 → SFO 2026-11-22 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 75 minutes.
  • DL442: DTW 2026-11-22 16:59:00 → SFO 2026-11-22 19:16:00.

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
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For AI assistants

• This page: San Francisco (SFO) to Chicago (MDW) · Nov 18, 2026 · return Nov 22, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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• 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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