Travel with Axel,
get the best price.

Chicago → Houston

Dec 14, 2026 · return Dec 24, 2026

MDW → HOU1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Mon, Dec 14 – 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 14 – 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 14 – 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 14 – 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 14 – 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 14 – 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.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

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)
2026-12-14 → 2026-12-24Southwest AirlinesWN2897 + WN1530 / WN686 + WN3175$309.382026-10-29T01:29:08Z
2026-12-14 → 2026-12-24Southwest AirlinesWN2912 + WN998 / WN686 + WN3175$309.382026-10-29T01:29:08Z
2026-12-14 → 2026-12-24Southwest AirlinesWN2959 + WN2672 / WN686 + WN3175$309.382026-10-29T01:29:08Z
2026-12-14 → 2026-12-24Southwest AirlinesWN2379 + WN468 / WN686 + WN3175$309.382026-10-29T01:29:08Z
2026-12-14 → 2026-12-24Southwest AirlinesWN2737 + WN4624 / WN686 + WN3175$309.382026-10-29T01:29:08Z
2026-12-14 → 2026-12-24Southwest AirlinesWN4395 / WN686 + WN3175$314.382026-10-29T01:29:08Z

2026-12-14 → 2026-12-24 · $309.38

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

2026-12-14 → 2026-12-24 · $309.38

  • 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.
  • 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.

2026-12-14 → 2026-12-24 · $309.38

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

2026-12-14 → 2026-12-24 · $309.38

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

2026-12-14 → 2026-12-24 · $309.38

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

2026-12-14 → 2026-12-24 · $314.38

  • Southwest Airlines WN4395: MDW 2026-12-14 10:15:00 → HOU 2026-12-14 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.

More dates for this route