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Houston → Chicago

Dec 13, 2026 · return Dec 14, 2026

HOU → MDW1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Sun, Dec 13 – Mon, Dec 14

Southwest Airlines
7:45 amHOU
4h 35m
SAT · 1h 5m
12:20 pmMDW
Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Mon, Dec 14

Southwest Airlines
7:10 amHOU
4h 55m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Mon, Dec 14

Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Mon, Dec 14

Southwest Airlines
2:55 pmHOU
4h 45m
CMH · 1h 10m
7:40 pmMDW
Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Mon, Dec 14

Southwest Airlines
2:45 pmHOU
5h 25m
PIT · 1h 15m
8:10 pmMDW
Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Mon, Dec 14

Southwest Airlines
5:15 pmHOU
2h 25m
Nonstop
7:40 pmMDW
Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU

Round-trip total · 1 adult · Taxes included

Make this trip yours

HOU ⇄ 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)
2026-12-13 → 2026-12-14Southwest AirlinesWN4547 + WN2348 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-12-13 → 2026-12-14Southwest AirlinesWN2173 + WN287 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-12-13 → 2026-12-14Southwest AirlinesWN686 + WN3175 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-12-13 → 2026-12-14Southwest AirlinesWN2211 + WN1718 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-12-13 → 2026-12-14Southwest AirlinesWN4610 + WN3556 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-12-13 → 2026-12-14Southwest AirlinesWN2134 / WN2912 + WN998$282.502026-10-29T01:04:53Z

2026-12-13 → 2026-12-14 · $275.00

  • Southwest Airlines WN4547 / WN2348: HOU 2026-12-13 07:45:00 → MDW 2026-12-13 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
    • WN4547: HOU 2026-12-13 07:45:00 → SAT 2026-12-13 08:45:00; layover at SAT: 65 minutes.
    • WN2348: SAT 2026-12-13 09:50:00 → MDW 2026-12-13 12:20:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-14 07:40:00 → HOU 2026-12-14 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-14 07:40:00 → CLT 2026-12-14 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-14 11:45:00 → HOU 2026-12-14 13:30:00.

2026-12-13 → 2026-12-14 · $275.00

  • Southwest Airlines WN2173 / WN287: HOU 2026-12-13 07:10:00 → MDW 2026-12-13 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2173: HOU 2026-12-13 07:10:00 → STL 2026-12-13 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-12-13 10:55:00 → MDW 2026-12-13 12:05:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-14 07:40:00 → HOU 2026-12-14 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-14 07:40:00 → CLT 2026-12-14 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-14 11:45:00 → HOU 2026-12-14 13:30:00.

2026-12-13 → 2026-12-14 · $275.00

  • Southwest Airlines WN686 / WN3175: HOU 2026-12-13 07:45:00 → MDW 2026-12-13 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-13 07:45:00 → MSY 2026-12-13 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-13 10:10:00 → MDW 2026-12-13 12:30:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-14 07:40:00 → HOU 2026-12-14 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-14 07:40:00 → CLT 2026-12-14 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-14 11:45:00 → HOU 2026-12-14 13:30:00.

2026-12-13 → 2026-12-14 · $275.00

  • Southwest Airlines WN2211 / WN1718: HOU 2026-12-13 14:55:00 → MDW 2026-12-13 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2026-12-13 14:55:00 → CMH 2026-12-13 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2026-12-13 19:30:00 → MDW 2026-12-13 19:40:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-14 07:40:00 → HOU 2026-12-14 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-14 07:40:00 → CLT 2026-12-14 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-14 11:45:00 → HOU 2026-12-14 13:30:00.

2026-12-13 → 2026-12-14 · $275.00

  • Southwest Airlines WN4610 / WN3556: HOU 2026-12-13 14:45:00 → MDW 2026-12-13 20:10:00; 1 stop(s) via PIT; 325 minutes. Local airport times.
    • WN4610: HOU 2026-12-13 14:45:00 → PIT 2026-12-13 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-12-13 19:40:00 → MDW 2026-12-13 20:10:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-14 07:40:00 → HOU 2026-12-14 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-14 07:40:00 → CLT 2026-12-14 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-14 11:45:00 → HOU 2026-12-14 13:30:00.

2026-12-13 → 2026-12-14 · $282.50

  • Southwest Airlines WN2134: HOU 2026-12-13 17:15:00 → MDW 2026-12-13 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2912 / WN998: MDW 2026-12-14 07:40:00 → HOU 2026-12-14 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-14 07:40:00 → CLT 2026-12-14 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-14 11:45:00 → HOU 2026-12-14 13:30:00.

More dates for this route