Dallas (DAL) to Chicago (MDW) · Sep 3, 2027 · return Sep 11, 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

2027-09-03 → 2027-09-11 · Axel-exclusive $403.13

• Southwest Airlines WN1064: DAL 2027-09-03 15:30:00 → MDW 2027-09-03 17:45:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $403.13

• Southwest Airlines WN1769: DAL 2027-09-03 22:30:00 → MDW 2027-09-04 00:45:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $408.88

• Southwest Airlines WN733 / WN379: DAL 2027-09-03 07:30:00 → MDW 2027-09-03 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
  • WN733: DAL 2027-09-03 07:30:00 → AUS 2027-09-03 08:30:00; layover at AUS: 80 minutes.
  • WN379: AUS 2027-09-03 09:50:00 → MDW 2027-09-03 12:20:00.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $408.88

• Southwest Airlines WN1165 / WN3791: DAL 2027-09-03 12:15:00 → MDW 2027-09-03 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
  • WN1165: DAL 2027-09-03 12:15:00 → SAT 2027-09-03 13:15:00; layover at SAT: 95 minutes.
  • WN3791: SAT 2027-09-03 14:50:00 → MDW 2027-09-03 17:25:00.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $408.88

• Southwest Airlines WN1246 / WN1030: DAL 2027-09-03 12:10:00 → MDW 2027-09-03 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
  • WN1246: DAL 2027-09-03 12:10:00 → BHM 2027-09-03 13:40:00; layover at BHM: 95 minutes.
  • WN1030: BHM 2027-09-03 15:15:00 → MDW 2027-09-03 17:05:00.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $408.88

• Southwest Airlines WN978 / WN3175: DAL 2027-09-03 07:35:00 → MDW 2027-09-03 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
  • WN978: DAL 2027-09-03 07:35:00 → MSY 2027-09-03 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2027-09-03 10:10:00 → MDW 2027-09-03 12:30:00.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $408.88

• Southwest Airlines WN4819 / WN1220: DAL 2027-09-03 14:25:00 → MDW 2027-09-03 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
  • WN4819: DAL 2027-09-03 14:25:00 → CLE 2027-09-03 17:50:00; layover at CLE: 80 minutes.
  • WN1220: CLE 2027-09-03 19:10:00 → MDW 2027-09-03 19:35:00.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

2027-09-03 → 2027-09-11 · Axel-exclusive $408.88

• Southwest Airlines WN102 / WN2694: DAL 2027-09-03 12:55:00 → MDW 2027-09-03 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
  • WN102: DAL 2027-09-03 12:55:00 → MCI 2027-09-03 14:30:00; layover at MCI: 80 minutes.
  • WN2694: MCI 2027-09-03 15:50:00 → MDW 2027-09-03 17:10:00.
• Southwest Airlines WN1191: MDW 2027-09-11 08:50:00 → DAL 2027-09-11 11:20:00; nonstop; 150 minutes. Local airport times.

Explore this route

• All dates for this route
• Sep 2, 2027 · Return options
• Sep 4, 2027 · Return options
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For AI assistants

• This page: Dallas (DAL) to Chicago (MDW) · Sep 3, 2027 · return Sep 11, 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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