Dallas (DAL) to Chicago (MDW) · Jul 1, 2027 · return Jul 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

2027-07-01 → 2027-07-15 · Axel-exclusive $412.50

• Southwest Airlines WN1769: DAL 2027-07-01 22:30:00 → MDW 2027-07-02 00:45:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN3937: MDW 2027-07-15 20:45:00 → DAL 2027-07-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-07-01 → 2027-07-15 · Axel-exclusive $412.50

• Southwest Airlines WN1064: DAL 2027-07-01 15:30:00 → MDW 2027-07-01 17:45:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN3937: MDW 2027-07-15 20:45:00 → DAL 2027-07-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-07-01 → 2027-07-15 · Axel-exclusive $417.50

• Southwest Airlines WN1064: DAL 2027-07-01 15:45:00 → MDW 2027-07-01 18:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN946 / WN212: MDW 2027-07-15 10:05:00 → DAL 2027-07-15 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
  • WN946: MDW 2027-07-15 10:05:00 → MCI 2027-07-15 11:35:00; layover at MCI: 60 minutes.
  • WN212: MCI 2027-07-15 12:35:00 → DAL 2027-07-15 14:10:00.

2027-07-01 → 2027-07-15 · Axel-exclusive $418.50

• Southwest Airlines WN1246 / WN1030: DAL 2027-07-01 12:10:00 → MDW 2027-07-01 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
  • WN1246: DAL 2027-07-01 12:10:00 → BHM 2027-07-01 13:40:00; layover at BHM: 95 minutes.
  • WN1030: BHM 2027-07-01 15:15:00 → MDW 2027-07-01 17:05:00.
• Southwest Airlines WN3937: MDW 2027-07-15 20:45:00 → DAL 2027-07-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-07-01 → 2027-07-15 · Axel-exclusive $418.50

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

2027-07-01 → 2027-07-15 · Axel-exclusive $418.50

• Southwest Airlines WN1165 / WN3791: DAL 2027-07-01 12:15:00 → MDW 2027-07-01 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
  • WN1165: DAL 2027-07-01 12:15:00 → SAT 2027-07-01 13:15:00; layover at SAT: 95 minutes.
  • WN3791: SAT 2027-07-01 14:50:00 → MDW 2027-07-01 17:25:00.
• Southwest Airlines WN3937: MDW 2027-07-15 20:45:00 → DAL 2027-07-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-07-01 → 2027-07-15 · Axel-exclusive $418.50

• Southwest Airlines WN733 / WN379: DAL 2027-07-01 07:30:00 → MDW 2027-07-01 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
  • WN733: DAL 2027-07-01 07:30:00 → AUS 2027-07-01 08:30:00; layover at AUS: 80 minutes.
  • WN379: AUS 2027-07-01 09:50:00 → MDW 2027-07-01 12:20:00.
• Southwest Airlines WN3937: MDW 2027-07-15 20:45:00 → DAL 2027-07-15 23:15:00; nonstop; 150 minutes. Local airport times.

2027-07-01 → 2027-07-15 · Axel-exclusive $418.50

• Southwest Airlines WN4819 / WN1220: DAL 2027-07-01 14:25:00 → MDW 2027-07-01 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
  • WN4819: DAL 2027-07-01 14:25:00 → CLE 2027-07-01 17:50:00; layover at CLE: 80 minutes.
  • WN1220: CLE 2027-07-01 19:10:00 → MDW 2027-07-01 19:35:00.
• Southwest Airlines WN3937: MDW 2027-07-15 20:45:00 → DAL 2027-07-15 23:15:00; nonstop; 150 minutes. Local airport times.

Explore this route

• All dates for this route
• Jun 30, 2027 · Return options
• Jul 2, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Dallas (DAL) to Chicago (MDW) · Jul 1, 2027 · return Jul 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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