Chicago (MDW) to Dallas (DAL), Dec 25–27, 2026: from $189 one way

Chicago (MDW) to Dallas (DAL), Dec 25–27, 2026: from $189 one way on Axel, checked Oct 29, 2026. Lowest published fare: $189 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 25, 2026, 1 adult, economy, checked Oct 29, 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: Chicago to Dallas (DAL) flight deals

2026-12-25 · one way · Axel-exclusive $203.00

• Southwest Airlines WN3937: MDW 2026-12-25 20:45:00 → DAL 2026-12-25 23:15:00; nonstop; 150 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $203.00

• Southwest Airlines WN1191: MDW 2026-12-26 08:50:00 → DAL 2026-12-26 11:20:00; nonstop; 150 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $203.00

• Southwest Airlines WN1191: MDW 2026-12-27 08:50:00 → DAL 2026-12-27 11:20:00; nonstop; 150 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $203.00

• Southwest Airlines WN1191: MDW 2026-12-25 08:50:00 → DAL 2026-12-25 11:20:00; nonstop; 150 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $203.00

• Southwest Airlines WN2092: MDW 2026-12-27 14:30:00 → DAL 2026-12-27 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $203.00

• Southwest Airlines WN3937: MDW 2026-12-26 20:45:00 → DAL 2026-12-26 23:15:00; nonstop; 150 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $189.00

• Southwest Airlines WN946 / WN212: MDW 2026-12-25 10:05:00 → DAL 2026-12-25 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
  • WN946: MDW 2026-12-25 10:05:00 → MCI 2026-12-25 11:35:00; layover at MCI: 60 minutes.
  • WN212: MCI 2026-12-25 12:35:00 → DAL 2026-12-25 14:10:00.

2026-12-27 · one way · Axel-exclusive $189.00

• Southwest Airlines WN1354 / WN1472: MDW 2026-12-27 13:20:00 → DAL 2026-12-27 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-12-27 13:20:00 → CMH 2026-12-27 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-12-27 16:50:00 → DAL 2026-12-27 18:25:00.

2026-12-25 · one way · Axel-exclusive $189.00

• Southwest Airlines WN3276 / WN1506: MDW 2026-12-25 10:00:00 → DAL 2026-12-25 15:40:00; 1 stop(s) via SAT; 340 minutes. Local airport times.
  • WN3276: MDW 2026-12-25 10:00:00 → SAT 2026-12-25 12:55:00; layover at SAT: 100 minutes.
  • WN1506: SAT 2026-12-25 14:35:00 → DAL 2026-12-25 15:40:00.

2026-12-25 · one way · Axel-exclusive $189.00

• Southwest Airlines WN1354 / WN1472: MDW 2026-12-25 13:20:00 → DAL 2026-12-25 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-12-25 13:20:00 → CMH 2026-12-25 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-12-25 16:50:00 → DAL 2026-12-25 18:25:00.

2026-12-25 · one way · Axel-exclusive $189.00

• Southwest Airlines WN2897 / WN1052: MDW 2026-12-25 17:25:00 → DAL 2026-12-25 22:55:00; 1 stop(s) via BNA; 330 minutes. Local airport times.
  • WN2897: MDW 2026-12-25 17:25:00 → BNA 2026-12-25 18:50:00; layover at BNA: 115 minutes.
  • WN1052: BNA 2026-12-25 20:45:00 → DAL 2026-12-25 22:55:00.

2026-12-26 · one way · Axel-exclusive $189.00

• Southwest Airlines WN1354 / WN1472: MDW 2026-12-26 13:20:00 → DAL 2026-12-26 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2026-12-26 13:20:00 → CMH 2026-12-26 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2026-12-26 16:50:00 → DAL 2026-12-26 18:25:00.

2026-12-27 · one way · Axel-exclusive $189.00

• Southwest Airlines WN3276 / WN1506: MDW 2026-12-27 10:00:00 → DAL 2026-12-27 15:40:00; 1 stop(s) via SAT; 340 minutes. Local airport times.
  • WN3276: MDW 2026-12-27 10:00:00 → SAT 2026-12-27 12:55:00; layover at SAT: 100 minutes.
  • WN1506: SAT 2026-12-27 14:35:00 → DAL 2026-12-27 15:40:00.

2026-12-26 · one way · Axel-exclusive $189.00

• Southwest Airlines WN2886 / WN1170: MDW 2026-12-26 13:20:00 → DAL 2026-12-26 18:40:00; 1 stop(s) via ATL; 320 minutes. Local airport times.
  • WN2886: MDW 2026-12-26 13:20:00 → ATL 2026-12-26 16:10:00; layover at ATL: 75 minutes.
  • WN1170: ATL 2026-12-26 17:25:00 → DAL 2026-12-26 18:40:00.

2026-12-25 · one way · Axel-exclusive $189.00

• Southwest Airlines WN4482 / WN54: MDW 2026-12-25 16:30:00 → DAL 2026-12-25 21:40:00; 1 stop(s) via HOU; 310 minutes. Local airport times.
  • WN4482: MDW 2026-12-25 16:30:00 → HOU 2026-12-25 19:10:00; layover at HOU: 80 minutes.
  • WN54: HOU 2026-12-25 20:30:00 → DAL 2026-12-25 21:40:00.

2026-12-26 · one way · Axel-exclusive $189.00

• Southwest Airlines WN946 / WN212: MDW 2026-12-26 10:05:00 → DAL 2026-12-26 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
  • WN946: MDW 2026-12-26 10:05:00 → MCI 2026-12-26 11:35:00; layover at MCI: 60 minutes.
  • WN212: MCI 2026-12-26 12:35:00 → DAL 2026-12-26 14:10:00.

2026-12-26 · one way · Axel-exclusive $189.00

• Southwest Airlines WN2897 / WN1052: MDW 2026-12-26 17:25:00 → DAL 2026-12-26 22:55:00; 1 stop(s) via BNA; 330 minutes. Local airport times.
  • WN2897: MDW 2026-12-26 17:25:00 → BNA 2026-12-26 18:50:00; layover at BNA: 115 minutes.
  • WN1052: BNA 2026-12-26 20:45:00 → DAL 2026-12-26 22:55:00.

2026-12-26 · one way · Axel-exclusive $189.00

• Southwest Airlines WN4482 / WN54: MDW 2026-12-26 16:30:00 → DAL 2026-12-26 21:40:00; 1 stop(s) via HOU; 310 minutes. Local airport times.
  • WN4482: MDW 2026-12-26 16:30:00 → HOU 2026-12-26 19:10:00; layover at HOU: 80 minutes.
  • WN54: HOU 2026-12-26 20:30:00 → DAL 2026-12-26 21:40:00.

2026-12-27 · one way · Axel-exclusive $189.00

• Southwest Airlines WN2897 / WN1052: MDW 2026-12-27 17:25:00 → DAL 2026-12-27 22:55:00; 1 stop(s) via BNA; 330 minutes. Local airport times.
  • WN2897: MDW 2026-12-27 17:25:00 → BNA 2026-12-27 18:50:00; layover at BNA: 115 minutes.
  • WN1052: BNA 2026-12-27 20:45:00 → DAL 2026-12-27 22:55:00.

2026-12-27 · one way · Axel-exclusive $189.00

• Southwest Airlines WN4482 / WN54: MDW 2026-12-27 16:30:00 → DAL 2026-12-27 21:40:00; 1 stop(s) via HOU; 310 minutes. Local airport times.
  • WN4482: MDW 2026-12-27 16:30:00 → HOU 2026-12-27 19:10:00; layover at HOU: 80 minutes.
  • WN54: HOU 2026-12-27 20:30:00 → DAL 2026-12-27 21:40:00.

2026-12-25 · one way · Axel-exclusive $189.00

• Southwest Airlines WN2886 / WN1170: MDW 2026-12-25 13:20:00 → DAL 2026-12-25 18:40:00; 1 stop(s) via ATL; 320 minutes. Local airport times.
  • WN2886: MDW 2026-12-25 13:20:00 → ATL 2026-12-25 16:10:00; layover at ATL: 75 minutes.
  • WN1170: ATL 2026-12-25 17:25:00 → DAL 2026-12-25 18:40:00.

2026-12-27 · one way · Axel-exclusive $189.00

• Southwest Airlines WN946 / WN212: MDW 2026-12-27 10:05:00 → DAL 2026-12-27 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
  • WN946: MDW 2026-12-27 10:05:00 → MCI 2026-12-27 11:35:00; layover at MCI: 60 minutes.
  • WN212: MCI 2026-12-27 12:35:00 → DAL 2026-12-27 14:10:00.

2026-12-26 · one way · Axel-exclusive $189.00

• Southwest Airlines WN3276 / WN1506: MDW 2026-12-26 10:00:00 → DAL 2026-12-26 15:40:00; 1 stop(s) via SAT; 340 minutes. Local airport times.
  • WN3276: MDW 2026-12-26 10:00:00 → SAT 2026-12-26 12:55:00; layover at SAT: 100 minutes.
  • WN1506: SAT 2026-12-26 14:35:00 → DAL 2026-12-26 15:40:00.

2026-12-27 · one way · Axel-exclusive $189.00

• Southwest Airlines WN2886 / WN1170: MDW 2026-12-27 13:20:00 → DAL 2026-12-27 18:40:00; 1 stop(s) via ATL; 320 minutes. Local airport times.
  • WN2886: MDW 2026-12-27 13:20:00 → ATL 2026-12-27 16:10:00; layover at ATL: 75 minutes.
  • WN1170: ATL 2026-12-27 17:25:00 → DAL 2026-12-27 18:40:00.

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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