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Chicago → Dallas

Dec 29, 2026 · return Dec 30, 2026

MDW → DAL1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Tue, Dec 29 – Wed, Dec 30

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

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Wed, Dec 30

Southwest Airlines
10:55 amMDW
2h 30m
Nonstop
1:25 pmDAL
Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Tue, Dec 29 – Wed, Dec 30

Southwest Airlines
1:20 pmMDW
5h 20m
ATL · 1h 15m
6:40 pmDAL
Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Wed, Dec 30

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

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Wed, Dec 30

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

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Wed, Dec 30

Southwest Airlines
10:00 amMDW
5h 40m
SAT · 1h 40m
3:40 pmDAL
Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Wed, Dec 30

Southwest Airlines
10:05 amMDW
4h 5m
MCI · 1h
2:10 pmDAL
Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW

Round-trip total · 1 adult · Taxes included

Tue, Dec 29 – Wed, Dec 30

Southwest Airlines
5:25 pmMDW
5h 30m
BNA · 1h 55m
10:55 pmDAL
Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ DAL

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 → 2026-12-30Southwest AirlinesWN3937 / WN1433$392.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN1080 / WN1433$392.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN2886 + WN1170 / WN1433$378.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN4482 + WN54 / WN1433$378.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN1354 + WN1472 / WN1433$378.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN3276 + WN1506 / WN1433$378.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN946 + WN212 / WN1433$378.002026-10-29T01:29:06Z
2026-12-29 → 2026-12-30Southwest AirlinesWN2897 + WN1052 / WN1433$378.002026-10-29T01:29:06Z

2026-12-29 → 2026-12-30 · $392.00

  • Southwest Airlines WN3937: MDW 2026-12-29 20:45:00 → DAL 2026-12-29 23:15:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

2026-12-29 → 2026-12-30 · $392.00

  • Southwest Airlines WN1080: MDW 2026-12-29 10:55:00 → DAL 2026-12-29 13:25:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

2026-12-29 → 2026-12-30 · $378.00

  • Southwest Airlines WN2886 / WN1170: MDW 2026-12-29 13:20:00 → DAL 2026-12-29 18:40:00; 1 stop(s) via ATL; 320 minutes. Local airport times.
    • WN2886: MDW 2026-12-29 13:20:00 → ATL 2026-12-29 16:10:00; layover at ATL: 75 minutes.
    • WN1170: ATL 2026-12-29 17:25:00 → DAL 2026-12-29 18:40:00.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

2026-12-29 → 2026-12-30 · $378.00

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

2026-12-29 → 2026-12-30 · $378.00

  • Southwest Airlines WN1354 / WN1472: MDW 2026-12-29 13:20:00 → DAL 2026-12-29 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2026-12-29 13:20:00 → CMH 2026-12-29 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2026-12-29 16:50:00 → DAL 2026-12-29 18:25:00.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

2026-12-29 → 2026-12-30 · $378.00

  • Southwest Airlines WN3276 / WN1506: MDW 2026-12-29 10:00:00 → DAL 2026-12-29 15:40:00; 1 stop(s) via SAT; 340 minutes. Local airport times.
    • WN3276: MDW 2026-12-29 10:00:00 → SAT 2026-12-29 12:55:00; layover at SAT: 100 minutes.
    • WN1506: SAT 2026-12-29 14:35:00 → DAL 2026-12-29 15:40:00.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

2026-12-29 → 2026-12-30 · $378.00

  • Southwest Airlines WN946 / WN212: MDW 2026-12-29 10:05:00 → DAL 2026-12-29 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
    • WN946: MDW 2026-12-29 10:05:00 → MCI 2026-12-29 11:35:00; layover at MCI: 60 minutes.
    • WN212: MCI 2026-12-29 12:35:00 → DAL 2026-12-29 14:10:00.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

2026-12-29 → 2026-12-30 · $378.00

  • Southwest Airlines WN2897 / WN1052: MDW 2026-12-29 17:25:00 → DAL 2026-12-29 22:55:00; 1 stop(s) via BNA; 330 minutes. Local airport times.
    • WN2897: MDW 2026-12-29 17:25:00 → BNA 2026-12-29 18:50:00; layover at BNA: 115 minutes.
    • WN1052: BNA 2026-12-29 20:45:00 → DAL 2026-12-29 22:55:00.
  • Southwest Airlines WN1433: DAL 2026-12-30 18:50:00 → MDW 2026-12-30 21:00:00; nonstop; 130 minutes. Local airport times.

More dates for this route