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Route overview: Chicago to Houston (HOU) flight deals

Chicago → Houston

Dec 21, 2026 · return Dec 24, 2026

MDW → HOU1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
7:45 amMDW
6h 15m
BHM · 2h 35m
2:00 pmHOU
Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
7:35 amMDW
5h 50m
MCI · 2h 10m
1:25 pmHOU
Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
11:30 amMDW
5h 35m
STL · 2h 15m
5:05 pmHOU
Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU
Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 24

Southwest Airlines
10:15 amMDW
2h 35m
Nonstop
12:50 pmHOU
Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 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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Explore this route

All dates for this routeDec 20, 2026 → Dec 23, 2026Dec 22, 2026 → Dec 25, 2026
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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Chicago to Houston (HOU) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2026-12-24Southwest AirlinesWN2379 + WN468 / WN686 + WN3175$343.762026-10-29T01:29:08Z
2026-12-21 → 2026-12-24Southwest AirlinesWN2959 + WN2672 / WN686 + WN3175$343.762026-10-29T01:29:08Z
2026-12-21 → 2026-12-24Southwest AirlinesWN2737 + WN4624 / WN686 + WN3175$343.762026-10-29T01:29:08Z
2026-12-21 → 2026-12-24Southwest AirlinesWN2912 + WN998 / WN686 + WN3175$343.762026-10-29T01:29:08Z
2026-12-21 → 2026-12-24Southwest AirlinesWN2897 + WN1530 / WN686 + WN3175$343.762026-10-29T01:29:08Z
2026-12-21 → 2026-12-24Southwest AirlinesWN4395 / WN686 + WN3175$350.012026-10-29T01:29:08Z

2026-12-21 → 2026-12-24 · $343.76

  • Southwest Airlines WN2379 / WN468: MDW 2026-12-21 07:45:00 → HOU 2026-12-21 14:00:00; 1 stop(s) via BHM; 375 minutes. Local airport times.
    • WN2379: MDW 2026-12-21 07:45:00 → BHM 2026-12-21 09:30:00; layover at BHM: 155 minutes.
    • WN468: BHM 2026-12-21 12:05:00 → HOU 2026-12-21 14:00:00.
  • Southwest Airlines WN686 / WN3175: HOU 2026-12-24 07:45:00 → MDW 2026-12-24 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-24 07:45:00 → MSY 2026-12-24 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-24 10:10:00 → MDW 2026-12-24 12:30:00.

2026-12-21 → 2026-12-24 · $343.76

  • Southwest Airlines WN2959 / WN2672: MDW 2026-12-21 07:35:00 → HOU 2026-12-21 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
    • WN2959: MDW 2026-12-21 07:35:00 → MCI 2026-12-21 09:05:00; layover at MCI: 130 minutes.
    • WN2672: MCI 2026-12-21 11:15:00 → HOU 2026-12-21 13:25:00.
  • Southwest Airlines WN686 / WN3175: HOU 2026-12-24 07:45:00 → MDW 2026-12-24 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-24 07:45:00 → MSY 2026-12-24 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-24 10:10:00 → MDW 2026-12-24 12:30:00.

2026-12-21 → 2026-12-24 · $343.76

  • Southwest Airlines WN2737 / WN4624: MDW 2026-12-21 11:30:00 → HOU 2026-12-21 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
    • WN2737: MDW 2026-12-21 11:30:00 → STL 2026-12-21 12:40:00; layover at STL: 135 minutes.
    • WN4624: STL 2026-12-21 14:55:00 → HOU 2026-12-21 17:05:00.
  • Southwest Airlines WN686 / WN3175: HOU 2026-12-24 07:45:00 → MDW 2026-12-24 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-24 07:45:00 → MSY 2026-12-24 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-24 10:10:00 → MDW 2026-12-24 12:30:00.

2026-12-21 → 2026-12-24 · $343.76

  • Southwest Airlines WN2912 / WN998: MDW 2026-12-21 07:40:00 → HOU 2026-12-21 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-21 07:40:00 → CLT 2026-12-21 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-21 11:45:00 → HOU 2026-12-21 13:30:00.
  • Southwest Airlines WN686 / WN3175: HOU 2026-12-24 07:45:00 → MDW 2026-12-24 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-24 07:45:00 → MSY 2026-12-24 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-24 10:10:00 → MDW 2026-12-24 12:30:00.

2026-12-21 → 2026-12-24 · $343.76

  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-21 17:25:00 → HOU 2026-12-21 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-21 17:25:00 → BNA 2026-12-21 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-21 20:45:00 → HOU 2026-12-21 23:00:00.
  • Southwest Airlines WN686 / WN3175: HOU 2026-12-24 07:45:00 → MDW 2026-12-24 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-24 07:45:00 → MSY 2026-12-24 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-24 10:10:00 → MDW 2026-12-24 12:30:00.

2026-12-21 → 2026-12-24 · $350.01

  • Southwest Airlines WN4395: MDW 2026-12-21 10:15:00 → HOU 2026-12-21 12:50:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN686 / WN3175: HOU 2026-12-24 07:45:00 → MDW 2026-12-24 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-24 07:45:00 → MSY 2026-12-24 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-24 10:10:00 → MDW 2026-12-24 12:30:00.

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For AI assistants

  • This page: Chicago (MDW) to Houston (HOU) · Dec 21, 2026 · return Dec 24, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Houston (HOU) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.