Dallas (DAL) to Chicago (MDW) · Nov 9, 2026 · return Nov 23, 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: Dallas-Fort Worth to Chicago (MDW) flight deals

2026-11-09 → 2026-11-23 · Axel-exclusive $335.00

• Southwest Airlines WN2565: DAL 2026-11-09 13:30:00 → MDW 2026-11-09 15:45:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-09 → 2026-11-23 · Axel-exclusive $340.00

• Southwest Airlines WN102 / WN2694: DAL 2026-11-09 12:55:00 → MDW 2026-11-09 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
  • WN102: DAL 2026-11-09 12:55:00 → MCI 2026-11-09 14:30:00; layover at MCI: 80 minutes.
  • WN2694: MCI 2026-11-09 15:50:00 → MDW 2026-11-09 17:10:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-09 → 2026-11-23 · Axel-exclusive $340.00

• Southwest Airlines WN978 / WN3175: DAL 2026-11-09 07:35:00 → MDW 2026-11-09 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
  • WN978: DAL 2026-11-09 07:35:00 → MSY 2026-11-09 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2026-11-09 10:10:00 → MDW 2026-11-09 12:30:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-09 → 2026-11-23 · Axel-exclusive $340.00

• Southwest Airlines WN1246 / WN1030: DAL 2026-11-09 12:10:00 → MDW 2026-11-09 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
  • WN1246: DAL 2026-11-09 12:10:00 → BHM 2026-11-09 13:40:00; layover at BHM: 95 minutes.
  • WN1030: BHM 2026-11-09 15:15:00 → MDW 2026-11-09 17:05:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-09 → 2026-11-23 · Axel-exclusive $340.00

• Southwest Airlines WN733 / WN379: DAL 2026-11-09 07:30:00 → MDW 2026-11-09 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
  • WN733: DAL 2026-11-09 07:30:00 → AUS 2026-11-09 08:30:00; layover at AUS: 80 minutes.
  • WN379: AUS 2026-11-09 09:50:00 → MDW 2026-11-09 12:20:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-09 → 2026-11-23 · Axel-exclusive $340.00

• Southwest Airlines WN1165 / WN3791: DAL 2026-11-09 12:15:00 → MDW 2026-11-09 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
  • WN1165: DAL 2026-11-09 12:15:00 → SAT 2026-11-09 13:15:00; layover at SAT: 95 minutes.
  • WN3791: SAT 2026-11-09 14:50:00 → MDW 2026-11-09 17:25:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

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.

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