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Route overview: Dallas-Fort Worth to Chicago (MDW) flight deals

Dallas → Chicago

Nov 18, 2026 · return Dec 2, 2026

DAL → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
6:40 amDAL
2h 10m
Nonstop
8:50 amMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
7:35 amDAL
4h 55m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
12:55 pmDAL
4h 15m
MCI · 1h 20m
5:10 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
2:25 pmDAL
5h 10m
CLE · 1h 20m
7:35 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
12:10 pmDAL
4h 55m
BHM · 1h 35m
5:05 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Wed, Nov 18 – Wed, Dec 2

Southwest Airlines
12:15 pmDAL
5h 10m
SAT · 1h 35m
5:25 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Make this trip yours

DAL ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeNov 17, 2026 → Dec 1, 2026Nov 19, 2026 → Dec 3, 2026
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Dallas-Fort Worth to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-18 → 2026-12-02Southwest AirlinesWN1433 / WN2092$330.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN1432 / WN2092$330.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN978 + WN3175 / WN2092$335.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN102 + WN2694 / WN2092$335.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN4819 + WN1220 / WN2092$335.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN1246 + WN1030 / WN2092$335.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN733 + WN379 / WN2092$335.002026-10-29T01:01:45Z
2026-11-18 → 2026-12-02Southwest AirlinesWN1165 + WN3791 / WN2092$335.002026-10-29T01:01:45Z

2026-11-18 → 2026-12-02 · $330.00

  • Southwest Airlines WN1433: DAL 2026-11-18 18:50:00 → MDW 2026-11-18 21:00:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $330.00

  • Southwest Airlines WN1432: DAL 2026-11-18 06:40:00 → MDW 2026-11-18 08:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $335.00

  • Southwest Airlines WN978 / WN3175: DAL 2026-11-18 07:35:00 → MDW 2026-11-18 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2026-11-18 07:35:00 → MSY 2026-11-18 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-11-18 10:10:00 → MDW 2026-11-18 12:30:00.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $335.00

  • Southwest Airlines WN102 / WN2694: DAL 2026-11-18 12:55:00 → MDW 2026-11-18 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2026-11-18 12:55:00 → MCI 2026-11-18 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2026-11-18 15:50:00 → MDW 2026-11-18 17:10:00.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $335.00

  • Southwest Airlines WN4819 / WN1220: DAL 2026-11-18 14:25:00 → MDW 2026-11-18 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
    • WN4819: DAL 2026-11-18 14:25:00 → CLE 2026-11-18 17:50:00; layover at CLE: 80 minutes.
    • WN1220: CLE 2026-11-18 19:10:00 → MDW 2026-11-18 19:35:00.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $335.00

  • Southwest Airlines WN1246 / WN1030: DAL 2026-11-18 12:10:00 → MDW 2026-11-18 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2026-11-18 12:10:00 → BHM 2026-11-18 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2026-11-18 15:15:00 → MDW 2026-11-18 17:05:00.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $335.00

  • Southwest Airlines WN733 / WN379: DAL 2026-11-18 07:30:00 → MDW 2026-11-18 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2026-11-18 07:30:00 → AUS 2026-11-18 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2026-11-18 09:50:00 → MDW 2026-11-18 12:20:00.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-18 → 2026-12-02 · $335.00

  • Southwest Airlines WN1165 / WN3791: DAL 2026-11-18 12:15:00 → MDW 2026-11-18 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
    • WN1165: DAL 2026-11-18 12:15:00 → SAT 2026-11-18 13:15:00; layover at SAT: 95 minutes.
    • WN3791: SAT 2026-11-18 14:50:00 → MDW 2026-11-18 17:25:00.
  • Southwest Airlines WN2092: MDW 2026-12-02 14:30:00 → DAL 2026-12-02 16:55:00; nonstop; 145 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Dallas (DAL) to Chicago (MDW) · Nov 18, 2026 · return Dec 2, 2026: 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.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Dallas-Fort Worth to Chicago (MDW) flight deals · Flight search guide.
  • 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.