Chicago (MDW) to Dallas (DAL) · Jan 24, 2027 · return Jan 31, 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: Chicago to Dallas (DAL) flight deals

2027-01-24 → 2027-01-31 · Axel-exclusive $266.00

• Southwest Airlines WN2092: MDW 2027-01-24 14:30:00 → DAL 2027-01-24 16:55:00; nonstop; 145 minutes. Local airport times.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $266.00

• Southwest Airlines WN1191: MDW 2027-01-24 08:50:00 → DAL 2027-01-24 11:20:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $256.50

• Southwest Airlines WN2886 / WN1170: MDW 2027-01-24 13:20:00 → DAL 2027-01-24 18:40:00; 1 stop(s) via ATL; 320 minutes. Local airport times.
  • WN2886: MDW 2027-01-24 13:20:00 → ATL 2027-01-24 16:10:00; layover at ATL: 75 minutes.
  • WN1170: ATL 2027-01-24 17:25:00 → DAL 2027-01-24 18:40:00.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $256.50

• Southwest Airlines WN4482 / WN54: MDW 2027-01-24 16:30:00 → DAL 2027-01-24 21:40:00; 1 stop(s) via HOU; 310 minutes. Local airport times.
  • WN4482: MDW 2027-01-24 16:30:00 → HOU 2027-01-24 19:10:00; layover at HOU: 80 minutes.
  • WN54: HOU 2027-01-24 20:30:00 → DAL 2027-01-24 21:40:00.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $256.50

• Southwest Airlines WN2897 / WN1052: MDW 2027-01-24 17:25:00 → DAL 2027-01-24 22:55:00; 1 stop(s) via BNA; 330 minutes. Local airport times.
  • WN2897: MDW 2027-01-24 17:25:00 → BNA 2027-01-24 18:50:00; layover at BNA: 115 minutes.
  • WN1052: BNA 2027-01-24 20:45:00 → DAL 2027-01-24 22:55:00.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $256.50

• Southwest Airlines WN3276 / WN1506: MDW 2027-01-24 10:00:00 → DAL 2027-01-24 15:40:00; 1 stop(s) via SAT; 340 minutes. Local airport times.
  • WN3276: MDW 2027-01-24 10:00:00 → SAT 2027-01-24 12:55:00; layover at SAT: 100 minutes.
  • WN1506: SAT 2027-01-24 14:35:00 → DAL 2027-01-24 15:40:00.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $256.50

• Southwest Airlines WN1354 / WN1472: MDW 2027-01-24 13:20:00 → DAL 2027-01-24 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
  • WN1354: MDW 2027-01-24 13:20:00 → CMH 2027-01-24 15:25:00; layover at CMH: 85 minutes.
  • WN1472: CMH 2027-01-24 16:50:00 → DAL 2027-01-24 18:25:00.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

2027-01-24 → 2027-01-31 · Axel-exclusive $256.50

• Southwest Airlines WN946 / WN212: MDW 2027-01-24 10:05:00 → DAL 2027-01-24 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
  • WN946: MDW 2027-01-24 10:05:00 → MCI 2027-01-24 11:35:00; layover at MCI: 60 minutes.
  • WN212: MCI 2027-01-24 12:35:00 → DAL 2027-01-24 14:10:00.
• Southwest Airlines WN1064: DAL 2027-01-31 15:45:00 → MDW 2027-01-31 18:00:00; nonstop; 135 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 23, 2027 · Return options
• Jan 25, 2027 · Return options
• Hotels in Dallas with Axel

For AI assistants

• This page: Chicago (MDW) to Dallas (DAL) · Jan 24, 2027 · return Jan 31, 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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