Dallas (DAL) to Chicago (MDW) · Jan 12, 2027 · return Jan 15, 2027

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

2027-01-12 → 2027-01-15 · Axel-exclusive $330.00

• Southwest Airlines WN1433: DAL 2027-01-12 17:40:00 → MDW 2027-01-12 19:55:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-12 → 2027-01-15 · Axel-exclusive $330.00

• Southwest Airlines WN1432: DAL 2027-01-12 08:45:00 → MDW 2027-01-12 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-12 → 2027-01-15 · Axel-exclusive $335.00

• Southwest Airlines WN1432: DAL 2027-01-12 13:40:00 → MDW 2027-01-12 15:55:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1354 / WN1472: MDW 2027-01-15 13:20:00 → DAL 2027-01-15 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2027-01-15 13:20:00 → CMH 2027-01-15 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2027-01-15 16:50:00 → DAL 2027-01-15 18:25:00.

2027-01-12 → 2027-01-15 · Axel-exclusive $335.00

• Southwest Airlines WN4819 / WN1220: DAL 2027-01-12 14:25:00 → MDW 2027-01-12 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
  • WN4819: DAL 2027-01-12 14:25:00 → CLE 2027-01-12 17:50:00; layover at CLE: 80 minutes.
  • WN1220: CLE 2027-01-12 19:10:00 → MDW 2027-01-12 19:35:00.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-12 → 2027-01-15 · Axel-exclusive $335.00

• Southwest Airlines WN1165 / WN3791: DAL 2027-01-12 12:15:00 → MDW 2027-01-12 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
  • WN1165: DAL 2027-01-12 12:15:00 → SAT 2027-01-12 13:15:00; layover at SAT: 95 minutes.
  • WN3791: SAT 2027-01-12 14:50:00 → MDW 2027-01-12 17:25:00.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-12 → 2027-01-15 · Axel-exclusive $335.00

• Southwest Airlines WN978 / WN3175: DAL 2027-01-12 07:35:00 → MDW 2027-01-12 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
  • WN978: DAL 2027-01-12 07:35:00 → MSY 2027-01-12 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-01-12 10:10:00 → MDW 2027-01-12 12:30:00.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-12 → 2027-01-15 · Axel-exclusive $335.00

• Southwest Airlines WN1246 / WN1030: DAL 2027-01-12 12:10:00 → MDW 2027-01-12 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
  • WN1246: DAL 2027-01-12 12:10:00 → BHM 2027-01-12 13:40:00; layover at BHM: 95 minutes.
  • WN1030: BHM 2027-01-12 15:15:00 → MDW 2027-01-12 17:05:00.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-12 → 2027-01-15 · Axel-exclusive $335.00

• Southwest Airlines WN102 / WN2694: DAL 2027-01-12 12:55:00 → MDW 2027-01-12 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
  • WN102: DAL 2027-01-12 12:55:00 → MCI 2027-01-12 14:30:00; layover at MCI: 80 minutes.
  • WN2694: MCI 2027-01-12 15:50:00 → MDW 2027-01-12 17:10:00.
• Southwest Airlines WN3937: MDW 2027-01-15 20:45:00 → DAL 2027-01-15 23:15:00; nonstop; 150 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 11, 2027 · Return options
• Jan 13, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Dallas (DAL) to Chicago (MDW) · Jan 12, 2027 · return Jan 15, 2027: 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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