Dallas (DAL) to Chicago (MDW) · Nov 20, 2026 · one way

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

2026-11-20 · one way · Axel-exclusive $170.00

• Southwest Airlines WN1433: DAL 2026-11-20 17:40:00 → MDW 2026-11-20 19:55:00; nonstop; 135 minutes. Local airport times.

2026-11-20 · one way · Axel-exclusive $170.00

• Southwest Airlines WN1432: DAL 2026-11-20 06:40:00 → MDW 2026-11-20 08:50:00; nonstop; 130 minutes. Local airport times.

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN1165 / WN3791: DAL 2026-11-20 12:15:00 → MDW 2026-11-20 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
  • WN1165: DAL 2026-11-20 12:15:00 → SAT 2026-11-20 13:15:00; layover at SAT: 95 minutes.
  • WN3791: SAT 2026-11-20 14:50:00 → MDW 2026-11-20 17:25:00.

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN733 / WN379: DAL 2026-11-20 07:30:00 → MDW 2026-11-20 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
  • WN733: DAL 2026-11-20 07:30:00 → AUS 2026-11-20 08:30:00; layover at AUS: 80 minutes.
  • WN379: AUS 2026-11-20 09:50:00 → MDW 2026-11-20 12:20:00.

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN1246 / WN1030: DAL 2026-11-20 12:10:00 → MDW 2026-11-20 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
  • WN1246: DAL 2026-11-20 12:10:00 → BHM 2026-11-20 13:40:00; layover at BHM: 95 minutes.
  • WN1030: BHM 2026-11-20 15:15:00 → MDW 2026-11-20 17:05:00.

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN102 / WN2694: DAL 2026-11-20 12:55:00 → MDW 2026-11-20 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
  • WN102: DAL 2026-11-20 12:55:00 → MCI 2026-11-20 14:30:00; layover at MCI: 80 minutes.
  • WN2694: MCI 2026-11-20 15:50:00 → MDW 2026-11-20 17:10:00.

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN4819 / WN1220: DAL 2026-11-20 14:25:00 → MDW 2026-11-20 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
  • WN4819: DAL 2026-11-20 14:25:00 → CLE 2026-11-20 17:50:00; layover at CLE: 80 minutes.
  • WN1220: CLE 2026-11-20 19:10:00 → MDW 2026-11-20 19:35:00.

2026-11-20 · one way · Axel-exclusive $175.00

• Southwest Airlines WN978 / WN3175: DAL 2026-11-20 07:35:00 → MDW 2026-11-20 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
  • WN978: DAL 2026-11-20 07:35:00 → MSY 2026-11-20 08:55:00; layover at MSY: 75 minutes.
  • WN3175: MSY 2026-11-20 10:10:00 → MDW 2026-11-20 12:30:00.

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.

Explore this route

• All dates for this route
• Nov 19, 2026 · Return options
• Nov 21, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Dallas (DAL) to Chicago (MDW) · Nov 20, 2026 · one way: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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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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