Dallas (DAL) to Chicago (MDW) · Nov 7, 2026 · return Nov 9, 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

2026-11-07 → 2026-11-09 · Axel-exclusive $330.00

• Southwest Airlines WN1064: DAL 2026-11-07 15:45:00 → MDW 2026-11-07 18:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1080: MDW 2026-11-09 10:55:00 → DAL 2026-11-09 13:25:00; nonstop; 150 minutes. Local airport times.

2026-11-07 → 2026-11-09 · Axel-exclusive $335.00

• Southwest Airlines WN1064: DAL 2026-11-07 15:30:00 → MDW 2026-11-07 17:45:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-09 13:20:00 → DAL 2026-11-09 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-09 13:20:00 → CMH 2026-11-09 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-09 16:50:00 → DAL 2026-11-09 18:25:00.

2026-11-07 → 2026-11-09 · Axel-exclusive $340.00

• Southwest Airlines WN1246 / WN1030: DAL 2026-11-07 12:10:00 → MDW 2026-11-07 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
  • WN1246: DAL 2026-11-07 12:10:00 → BHM 2026-11-07 13:40:00; layover at BHM: 95 minutes.
  • WN1030: BHM 2026-11-07 15:15:00 → MDW 2026-11-07 17:05:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-09 13:20:00 → DAL 2026-11-09 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-09 13:20:00 → CMH 2026-11-09 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-09 16:50:00 → DAL 2026-11-09 18:25:00.

2026-11-07 → 2026-11-09 · Axel-exclusive $340.00

• Southwest Airlines WN102 / WN2694: DAL 2026-11-07 12:55:00 → MDW 2026-11-07 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
  • WN102: DAL 2026-11-07 12:55:00 → MCI 2026-11-07 14:30:00; layover at MCI: 80 minutes.
  • WN2694: MCI 2026-11-07 15:50:00 → MDW 2026-11-07 17:10:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-09 13:20:00 → DAL 2026-11-09 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-09 13:20:00 → CMH 2026-11-09 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-09 16:50:00 → DAL 2026-11-09 18:25:00.

2026-11-07 → 2026-11-09 · Axel-exclusive $340.00

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

2026-11-07 → 2026-11-09 · Axel-exclusive $340.00

• Southwest Airlines WN4819 / WN1220: DAL 2026-11-07 14:25:00 → MDW 2026-11-07 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
  • WN4819: DAL 2026-11-07 14:25:00 → CLE 2026-11-07 17:50:00; layover at CLE: 80 minutes.
  • WN1220: CLE 2026-11-07 19:10:00 → MDW 2026-11-07 19:35:00.
• Southwest Airlines WN1354 / WN1472: MDW 2026-11-09 13:20:00 → DAL 2026-11-09 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-11-09 13:20:00 → CMH 2026-11-09 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-11-09 16:50:00 → DAL 2026-11-09 18:25:00.

2026-11-07 → 2026-11-09 · Axel-exclusive $340.00

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

Explore this route

• All dates for this route
• Nov 6, 2026 · Return options
• Nov 8, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

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