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Chicago → Houston

Dec 19, 2026 · return Dec 29, 2026

MDW → HOU1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
10:15 amMDW
2h 35m
Nonstop
12:50 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Dec 19 – Tue, Dec 29

Delta Air Lines
1:02 pmMDW
6h 14m
ATL · 1h 59m
7:16 pmHOU
Delta Air Lines
10:41 amHOU
5h 37m
ATL · 1h 50m
4:18 pmMDW

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
7:35 amMDW
5h 50m
MCI · 2h 10m
1:25 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
11:30 amMDW
5h 35m
STL · 2h 15m
5:05 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Sat, Dec 19 – Tue, Dec 29

Southwest Airlines
7:45 amMDW
6h 15m
BHM · 2h 35m
2:00 pmHOU
Southwest Airlines
2:35 pmHOU
2h 25m
Nonstop
5:00 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ HOU

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 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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)
2026-12-19 → 2026-12-29Southwest AirlinesWN2127 / WN2133$349.132026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Delta Air LinesDL2417 + DL2051 / DL1509 + DL1728$428.752026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Southwest AirlinesWN4482 / WN2133$349.132026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Southwest AirlinesWN2959 + WN2672 / WN2133$342.882026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Southwest AirlinesWN2737 + WN4624 / WN2133$342.882026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Southwest AirlinesWN2912 + WN998 / WN2133$342.882026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Southwest AirlinesWN2897 + WN1530 / WN2133$342.882026-10-29T01:29:08Z
2026-12-19 → 2026-12-29Southwest AirlinesWN2379 + WN468 / WN2133$342.882026-10-29T01:29:08Z

2026-12-19 → 2026-12-29 · $349.13

  • Southwest Airlines WN2127: MDW 2026-12-19 10:15:00 → HOU 2026-12-19 12:50:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-29 · $428.75

  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-19 13:02:00 → HOU 2026-12-19 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-19 13:02:00 → ATL 2026-12-19 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-19 18:00:00 → HOU 2026-12-19 19:16:00.
  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-29 10:41:00 → MDW 2026-12-29 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-29 10:41:00 → ATL 2026-12-29 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-29 15:25:00 → MDW 2026-12-29 16:18:00.

2026-12-19 → 2026-12-29 · $349.13

  • Southwest Airlines WN4482: MDW 2026-12-19 16:30:00 → HOU 2026-12-19 19:10:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-29 · $342.88

  • Southwest Airlines WN2959 / WN2672: MDW 2026-12-19 07:35:00 → HOU 2026-12-19 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
    • WN2959: MDW 2026-12-19 07:35:00 → MCI 2026-12-19 09:05:00; layover at MCI: 130 minutes.
    • WN2672: MCI 2026-12-19 11:15:00 → HOU 2026-12-19 13:25:00.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-29 · $342.88

  • Southwest Airlines WN2737 / WN4624: MDW 2026-12-19 11:30:00 → HOU 2026-12-19 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
    • WN2737: MDW 2026-12-19 11:30:00 → STL 2026-12-19 12:40:00; layover at STL: 135 minutes.
    • WN4624: STL 2026-12-19 14:55:00 → HOU 2026-12-19 17:05:00.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-29 · $342.88

  • Southwest Airlines WN2912 / WN998: MDW 2026-12-19 07:40:00 → HOU 2026-12-19 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-19 07:40:00 → CLT 2026-12-19 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-19 11:45:00 → HOU 2026-12-19 13:30:00.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-29 · $342.88

  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-19 17:25:00 → HOU 2026-12-19 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-19 17:25:00 → BNA 2026-12-19 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-19 20:45:00 → HOU 2026-12-19 23:00:00.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

2026-12-19 → 2026-12-29 · $342.88

  • Southwest Airlines WN2379 / WN468: MDW 2026-12-19 07:45:00 → HOU 2026-12-19 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
    • WN2379: MDW 2026-12-19 07:45:00 → BHM 2026-12-19 09:30:00; layover at BHM: 155 minutes.
    • WN468: BHM 2026-12-19 12:05:00 → HOU 2026-12-19 14:00:00.
  • Southwest Airlines WN2133: HOU 2026-12-29 14:35:00 → MDW 2026-12-29 17:00:00; nonstop; 145 minutes. Local airport times.

More dates for this route