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DAL → MDW1 adulteconomy

23 flight options · 1 airline

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
5:40 pmDAL
2h 15m
Nonstop
7:55 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:40 amDAL
2h 10m
Nonstop
8:50 amMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
12:10 pmDAL
4h 55m
BHM · 1h 35m
5:05 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:35 amDAL
4h 55m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
12:55 pmDAL
4h 15m
MCI · 1h 20m
5:10 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
12:15 pmDAL
5h 10m
SAT · 1h 35m
5:25 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Show 7 more flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:40 pmDAL
2h 15m
Nonstop
7:55 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
12:15 pmDAL
5h 10m
SAT · 1h 35m
5:25 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:35 amDAL
4h 55m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
12:10 pmDAL
4h 55m
BHM · 1h 35m
5:05 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
12:55 pmDAL
4h 15m
MCI · 1h 20m
5:10 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:40 amDAL
2h 10m
Nonstop
8:50 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
12:15 pmDAL
5h 10m
SAT · 1h 35m
5:25 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way 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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More dates

Nov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-20 · one waySouthwest AirlinesWN1433$170.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1433 / WN2092$330.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1433 / WN3937$379.502026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN1432$170.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1432 / WN3937$379.502026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN1165 + WN3791$175.002026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN733 + WN379$175.002026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN1246 + WN1030$175.002026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN102 + WN2694$175.002026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN4819 + WN1220$175.002026-10-29T01:01:45Z
2026-11-20 · one waySouthwest AirlinesWN978 + WN3175$175.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1433 / WN1354 + WN1472$335.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1246 + WN1030 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN978 + WN3175 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN102 + WN2694 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1165 + WN3791 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2026-11-20 → 2026-11-23Southwest AirlinesWN733 + WN379 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1433 / WN1354 + WN1472$384.502026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1165 + WN3791 / WN3937$386.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN978 + WN3175 / WN3937$386.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN733 + WN379 / WN3937$386.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1246 + WN1030 / WN3937$386.002026-10-29T01:01:45Z
2026-11-27 → 2026-12-04Southwest AirlinesWN102 + WN2694 / WN3937$386.002026-10-29T01:01:45Z

2026-11-20 · one way · $170.00

  • Southwest Airlines WN1433: DAL 2026-11-20 18:50:00 → MDW 2026-11-20 21:00:00; nonstop; 130 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $330.00

  • Southwest Airlines WN1433: DAL 2026-11-20 17:40:00 → MDW 2026-11-20 19:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2026-11-23 14:30:00 → DAL 2026-11-23 16:55:00; nonstop; 145 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $379.50

  • Southwest Airlines WN1433: DAL 2026-11-27 18:50:00 → MDW 2026-11-27 21:00:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

2026-11-20 · one way · $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.

2026-11-27 → 2026-12-04 · $379.50

  • Southwest Airlines WN1432: DAL 2026-11-27 06:40:00 → MDW 2026-11-27 08:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

2026-11-20 · one way · $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 · $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 · $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 · $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 · $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 · $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.

2026-11-20 → 2026-11-23 · $335.00

  • Southwest Airlines WN1433: DAL 2026-11-20 18:50:00 → MDW 2026-11-20 21:00:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-20 → 2026-11-23 · $340.00

  • 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.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-20 → 2026-11-23 · $340.00

  • 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.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-20 → 2026-11-23 · $340.00

  • 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.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-20 → 2026-11-23 · $340.00

  • 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.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-20 → 2026-11-23 · $340.00

  • 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.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-11-23 13:20:00 → DAL 2026-11-23 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-11-23 13:20:00 → CMH 2026-11-23 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-11-23 16:50:00 → DAL 2026-11-23 18:25:00.

2026-11-27 → 2026-12-04 · $384.50

  • Southwest Airlines WN1433: DAL 2026-11-27 17:40:00 → MDW 2026-11-27 19:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN1354 / WN1472: MDW 2026-12-04 13:20:00 → DAL 2026-12-04 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-12-04 13:20:00 → CMH 2026-12-04 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-12-04 16:50:00 → DAL 2026-12-04 18:25:00.

2026-11-27 → 2026-12-04 · $386.00

  • Southwest Airlines WN1165 / WN3791: DAL 2026-11-27 12:15:00 → MDW 2026-11-27 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
    • WN1165: DAL 2026-11-27 12:15:00 → SAT 2026-11-27 13:15:00; layover at SAT: 95 minutes.
    • WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $386.00

  • Southwest Airlines WN978 / WN3175: DAL 2026-11-27 07:35:00 → MDW 2026-11-27 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2026-11-27 07:35:00 → MSY 2026-11-27 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-11-27 10:10:00 → MDW 2026-11-27 12:30:00.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $386.00

  • Southwest Airlines WN733 / WN379: DAL 2026-11-27 07:30:00 → MDW 2026-11-27 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2026-11-27 07:30:00 → AUS 2026-11-27 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2026-11-27 09:50:00 → MDW 2026-11-27 12:20:00.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $386.00

  • Southwest Airlines WN1246 / WN1030: DAL 2026-11-27 12:10:00 → MDW 2026-11-27 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2026-11-27 12:10:00 → BHM 2026-11-27 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2026-11-27 15:15:00 → MDW 2026-11-27 17:05:00.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $386.00

  • Southwest Airlines WN102 / WN2694: DAL 2026-11-27 12:55:00 → MDW 2026-11-27 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2026-11-27 12:55:00 → MCI 2026-11-27 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2026-11-27 15:50:00 → MDW 2026-11-27 17:10:00.
  • Southwest Airlines WN3937: MDW 2026-12-04 20:45:00 → DAL 2026-12-04 23:15:00; nonstop; 150 minutes. Local airport times.

More dates for this route