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Dallas → Chicago

Dec 29, 2026 · return Jan 3, 2027

DAL → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Tue, Dec 29 – Sun, Jan 3

Southwest Airlines
8:45 amDAL
2h 15m
Nonstop
11:00 amMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sun, Jan 3

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

One-stop flights

Tue, Dec 29 – Sun, Jan 3

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

Tue, Dec 29 – Sun, Jan 3

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

Tue, Dec 29 – Sun, Jan 3

Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW
Southwest Airlines
4:30 pmMDW
5h 10m
HOU · 1h 20m
9:40 pmDAL

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Sun, Jan 3

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

Tue, Dec 29 – Sun, Jan 3

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

Tue, Dec 29 – Sun, Jan 3

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

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

All dates for this routeNov 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)
2026-12-29 → 2027-01-03Southwest AirlinesWN1432 / WN2092$412.502026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN1433 / WN2092$412.502026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN978 + WN3175 / WN2092$418.752026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN1165 + WN3791 / WN2092$418.752026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN1433 / WN4482 + WN54$418.752026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN1246 + WN1030 / WN2092$418.752026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN102 + WN2694 / WN2092$418.752026-10-29T01:01:45Z
2026-12-29 → 2027-01-03Southwest AirlinesWN733 + WN379 / WN2092$418.752026-10-29T01:01:45Z

2026-12-29 → 2027-01-03 · $412.50

  • Southwest Airlines WN1432: DAL 2026-12-29 08:45:00 → MDW 2026-12-29 11:00:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-29 → 2027-01-03 · $412.50

  • Southwest Airlines WN1433: DAL 2026-12-29 17:40:00 → MDW 2026-12-29 19:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-29 → 2027-01-03 · $418.75

  • Southwest Airlines WN978 / WN3175: DAL 2026-12-29 07:35:00 → MDW 2026-12-29 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2026-12-29 07:35:00 → MSY 2026-12-29 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-29 10:10:00 → MDW 2026-12-29 12:30:00.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-29 → 2027-01-03 · $418.75

  • Southwest Airlines WN1165 / WN3791: DAL 2026-12-29 12:15:00 → MDW 2026-12-29 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
    • WN1165: DAL 2026-12-29 12:15:00 → SAT 2026-12-29 13:15:00; layover at SAT: 95 minutes.
    • WN3791: SAT 2026-12-29 14:50:00 → MDW 2026-12-29 17:25:00.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-29 → 2027-01-03 · $418.75

  • Southwest Airlines WN1433: DAL 2026-12-29 18:50:00 → MDW 2026-12-29 21:00:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN4482 / WN54: MDW 2027-01-03 16:30:00 → DAL 2027-01-03 21:40:00; 1 stop(s) via HOU; 310 minutes. Local airport times.
    • WN4482: MDW 2027-01-03 16:30:00 → HOU 2027-01-03 19:10:00; layover at HOU: 80 minutes.
    • WN54: HOU 2027-01-03 20:30:00 → DAL 2027-01-03 21:40:00.

2026-12-29 → 2027-01-03 · $418.75

  • Southwest Airlines WN1246 / WN1030: DAL 2026-12-29 12:10:00 → MDW 2026-12-29 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2026-12-29 12:10:00 → BHM 2026-12-29 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2026-12-29 15:15:00 → MDW 2026-12-29 17:05:00.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-29 → 2027-01-03 · $418.75

  • Southwest Airlines WN102 / WN2694: DAL 2026-12-29 12:55:00 → MDW 2026-12-29 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2026-12-29 12:55:00 → MCI 2026-12-29 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2026-12-29 15:50:00 → MDW 2026-12-29 17:10:00.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

2026-12-29 → 2027-01-03 · $418.75

  • Southwest Airlines WN733 / WN379: DAL 2026-12-29 07:30:00 → MDW 2026-12-29 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2026-12-29 07:30:00 → AUS 2026-12-29 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2026-12-29 09:50:00 → MDW 2026-12-29 12:20:00.
  • Southwest Airlines WN2092: MDW 2027-01-03 14:30:00 → DAL 2027-01-03 16:55:00; nonstop; 145 minutes. Local airport times.

More dates for this route