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

Dallas → Chicago

Jan 27, 2027 · return Feb 10, 2027

DAL → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Wed, Jan 27 – Wed, Feb 10

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, Jan 27 – Wed, Feb 10

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, Jan 27 – Wed, Feb 10

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, Jan 27 – Wed, Feb 10

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, Jan 27 – Wed, Feb 10

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, Jan 27 – Wed, Feb 10

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, Jan 27 – Wed, Feb 10

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

Wed, Jan 27 – Wed, Feb 10

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

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 routeJan 26, 2027 → Feb 9, 2027Jan 28, 2027 → Feb 11, 2027
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)
2027-01-27 → 2027-02-10Southwest AirlinesWN1433 / WN2092$330.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN1432 / WN2092$330.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN1246 + WN1030 / WN2092$335.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN733 + WN379 / WN2092$335.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN4819 + WN1220 / WN2092$335.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN978 + WN3175 / WN2092$335.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN1165 + WN3791 / WN2092$335.002026-10-29T01:01:45Z
2027-01-27 → 2027-02-10Southwest AirlinesWN102 + WN2694 / WN2092$335.002026-10-29T01:01:45Z

2027-01-27 → 2027-02-10 · $330.00

  • Southwest Airlines WN1433: DAL 2027-01-27 18:50:00 → MDW 2027-01-27 21:00:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $330.00

  • Southwest Airlines WN1432: DAL 2027-01-27 06:40:00 → MDW 2027-01-27 08:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $335.00

  • Southwest Airlines WN1246 / WN1030: DAL 2027-01-27 12:10:00 → MDW 2027-01-27 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2027-01-27 12:10:00 → BHM 2027-01-27 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2027-01-27 15:15:00 → MDW 2027-01-27 17:05:00.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $335.00

  • Southwest Airlines WN733 / WN379: DAL 2027-01-27 07:30:00 → MDW 2027-01-27 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2027-01-27 07:30:00 → AUS 2027-01-27 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2027-01-27 09:50:00 → MDW 2027-01-27 12:20:00.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $335.00

  • Southwest Airlines WN4819 / WN1220: DAL 2027-01-27 14:25:00 → MDW 2027-01-27 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
    • WN4819: DAL 2027-01-27 14:25:00 → CLE 2027-01-27 17:50:00; layover at CLE: 80 minutes.
    • WN1220: CLE 2027-01-27 19:10:00 → MDW 2027-01-27 19:35:00.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $335.00

  • Southwest Airlines WN978 / WN3175: DAL 2027-01-27 07:35:00 → MDW 2027-01-27 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2027-01-27 07:35:00 → MSY 2027-01-27 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2027-01-27 10:10:00 → MDW 2027-01-27 12:30:00.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $335.00

  • Southwest Airlines WN1165 / WN3791: DAL 2027-01-27 12:15:00 → MDW 2027-01-27 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
    • WN1165: DAL 2027-01-27 12:15:00 → SAT 2027-01-27 13:15:00; layover at SAT: 95 minutes.
    • WN3791: SAT 2027-01-27 14:50:00 → MDW 2027-01-27 17:25:00.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-27 → 2027-02-10 · $335.00

  • Southwest Airlines WN102 / WN2694: DAL 2027-01-27 12:55:00 → MDW 2027-01-27 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2027-01-27 12:55:00 → MCI 2027-01-27 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2027-01-27 15:50:00 → MDW 2027-01-27 17:10:00.
  • Southwest Airlines WN2092: MDW 2027-02-10 14:30:00 → DAL 2027-02-10 16:55:00; nonstop; 145 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Dallas (DAL) to Chicago (MDW) · Jan 27, 2027 · return Feb 10, 2027: 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.