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Houston → Chicago

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HOU → MDW1 adulteconomy

20 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:10 amHOU
4h 55m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:45 pmHOU
5h 25m
PIT · 1h 15m
8:10 pmMDW
Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU

Round-trip total · 1 adult · Taxes included

Show 4 more flights

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:45 amHOU
4h 35m
SAT · 1h 5m
12:20 pmMDW
Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:55 pmHOU
4h 45m
CMH · 1h 10m
7:40 pmMDW
Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:15 pmHOU
2h 25m
Nonstop
7:40 pmMDW
Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
5:15 pmHOU
2h 25m
Nonstop
7:40 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
10:41 amHOU
5h 37m
ATL · 1h 50m
4:18 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:45 amHOU
4h 35m
SAT · 1h 5m
12:20 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:45 pmHOU
5h 25m
PIT · 1h 15m
8:10 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:10 amHOU
4h 55m
STL · 1h 45m
12:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:55 pmHOU
4h 45m
CMH · 1h 10m
7:40 pmMDW

One-way 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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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

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN2134$150.002026-10-29T01:04:53Z
2026-11-20 · one wayDelta Air LinesDL1509 + DL1728$205.002026-10-29T01:04:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4610 + WN3556 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2173 + WN287 / WN2897 + WN1530$323.132026-10-29T01:04:53Z
2026-11-20 · one waySouthwest AirlinesWN1654$150.002026-10-29T01:04:53Z
2026-11-20 · one waySouthwest AirlinesWN4547 + WN2348$140.002026-10-29T01:04:53Z
2026-11-20 · one waySouthwest AirlinesWN4610 + WN3556$140.002026-10-29T01:04:53Z
2026-11-20 · one waySouthwest AirlinesWN686 + WN3175$140.002026-10-29T01:04:53Z
2026-11-20 · one waySouthwest AirlinesWN2173 + WN287$140.002026-10-29T01:04:53Z
2026-11-20 · one waySouthwest AirlinesWN2211 + WN1718$140.002026-10-29T01:04:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN686 + WN3175 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2173 + WN287 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2211 + WN1718 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4547 + WN2348 / WN2912 + WN998$275.002026-10-29T01:04:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2134 / WN2912 + WN998$282.502026-10-29T01:04:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4610 + WN3556 / WN2897 + WN1530$323.132026-10-29T01:04:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN686 + WN3175 / WN2897 + WN1530$323.132026-10-29T01:04:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4547 + WN2348 / WN2897 + WN1530$323.132026-10-29T01:04:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2211 + WN1718 / WN2897 + WN1530$323.132026-10-29T01:04:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2134 / WN2897 + WN1530$333.252026-10-29T01:04:53Z

2026-11-20 · one way · $150.00

  • Southwest Airlines WN2134: HOU 2026-11-20 17:15:00 → MDW 2026-11-20 19:40:00; nonstop; 145 minutes. Local airport times.

2026-11-20 · one way · $205.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-11-20 10:41:00 → MDW 2026-11-20 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-11-20 10:41:00 → ATL 2026-11-20 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-11-20 15:25:00 → MDW 2026-11-20 16:18:00.

2026-11-20 → 2026-11-23 · $275.00

  • Southwest Airlines WN4610 / WN3556: HOU 2026-11-20 14:45:00 → MDW 2026-11-20 20:10:00; 1 stop(s) via PIT; 325 minutes. Local airport times.
    • WN4610: HOU 2026-11-20 14:45:00 → PIT 2026-11-20 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-11-20 19:40:00 → MDW 2026-11-20 20:10:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-11-23 07:40:00 → HOU 2026-11-23 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-11-23 07:40:00 → CLT 2026-11-23 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-11-23 11:45:00 → HOU 2026-11-23 13:30:00.

2026-11-27 → 2026-12-04 · $323.13

  • Southwest Airlines WN2173 / WN287: HOU 2026-11-27 07:10:00 → MDW 2026-11-27 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2173: HOU 2026-11-27 07:10:00 → STL 2026-11-27 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-11-27 10:55:00 → MDW 2026-11-27 12:05:00.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-04 17:25:00 → HOU 2026-12-04 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-04 20:45:00 → HOU 2026-12-04 23:00:00.

2026-11-20 · one way · $150.00

  • Southwest Airlines WN1654: HOU 2026-11-20 22:20:00 → MDW 2026-11-21 00:50:00; nonstop; 150 minutes. Local airport times.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN4547 / WN2348: HOU 2026-11-20 07:45:00 → MDW 2026-11-20 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
    • WN4547: HOU 2026-11-20 07:45:00 → SAT 2026-11-20 08:45:00; layover at SAT: 65 minutes.
    • WN2348: SAT 2026-11-20 09:50:00 → MDW 2026-11-20 12:20:00.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN4610 / WN3556: HOU 2026-11-20 14:45:00 → MDW 2026-11-20 20:10:00; 1 stop(s) via PIT; 325 minutes. Local airport times.
    • WN4610: HOU 2026-11-20 14:45:00 → PIT 2026-11-20 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-11-20 19:40:00 → MDW 2026-11-20 20:10:00.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN686 / WN3175: HOU 2026-11-20 07:45:00 → MDW 2026-11-20 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-11-20 07:45:00 → MSY 2026-11-20 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-11-20 10:10:00 → MDW 2026-11-20 12:30:00.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN2173 / WN287: HOU 2026-11-20 07:10:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2173: HOU 2026-11-20 07:10:00 → STL 2026-11-20 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN2211 / WN1718: HOU 2026-11-20 14:55:00 → MDW 2026-11-20 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2026-11-20 14:55:00 → CMH 2026-11-20 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2026-11-20 19:30:00 → MDW 2026-11-20 19:40:00.

2026-11-20 → 2026-11-23 · $275.00

  • Southwest Airlines WN686 / WN3175: HOU 2026-11-20 07:45:00 → MDW 2026-11-20 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-11-20 07:45:00 → MSY 2026-11-20 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-11-20 10:10:00 → MDW 2026-11-20 12:30:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-11-23 07:40:00 → HOU 2026-11-23 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-11-23 07:40:00 → CLT 2026-11-23 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-11-23 11:45:00 → HOU 2026-11-23 13:30:00.

2026-11-20 → 2026-11-23 · $275.00

  • Southwest Airlines WN2173 / WN287: HOU 2026-11-20 07:10:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2173: HOU 2026-11-20 07:10:00 → STL 2026-11-20 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-11-23 07:40:00 → HOU 2026-11-23 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-11-23 07:40:00 → CLT 2026-11-23 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-11-23 11:45:00 → HOU 2026-11-23 13:30:00.

2026-11-20 → 2026-11-23 · $275.00

  • Southwest Airlines WN2211 / WN1718: HOU 2026-11-20 14:55:00 → MDW 2026-11-20 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2026-11-20 14:55:00 → CMH 2026-11-20 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2026-11-20 19:30:00 → MDW 2026-11-20 19:40:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-11-23 07:40:00 → HOU 2026-11-23 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-11-23 07:40:00 → CLT 2026-11-23 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-11-23 11:45:00 → HOU 2026-11-23 13:30:00.

2026-11-20 → 2026-11-23 · $275.00

  • Southwest Airlines WN4547 / WN2348: HOU 2026-11-20 07:45:00 → MDW 2026-11-20 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
    • WN4547: HOU 2026-11-20 07:45:00 → SAT 2026-11-20 08:45:00; layover at SAT: 65 minutes.
    • WN2348: SAT 2026-11-20 09:50:00 → MDW 2026-11-20 12:20:00.
  • Southwest Airlines WN2912 / WN998: MDW 2026-11-23 07:40:00 → HOU 2026-11-23 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-11-23 07:40:00 → CLT 2026-11-23 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-11-23 11:45:00 → HOU 2026-11-23 13:30:00.

2026-11-20 → 2026-11-23 · $282.50

  • Southwest Airlines WN2134: HOU 2026-11-20 17:15:00 → MDW 2026-11-20 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2912 / WN998: MDW 2026-11-23 07:40:00 → HOU 2026-11-23 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-11-23 07:40:00 → CLT 2026-11-23 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-11-23 11:45:00 → HOU 2026-11-23 13:30:00.

2026-11-27 → 2026-12-04 · $323.13

  • Southwest Airlines WN4610 / WN3556: HOU 2026-11-27 14:45:00 → MDW 2026-11-27 20:10:00; 1 stop(s) via PIT; 325 minutes. Local airport times.
    • WN4610: HOU 2026-11-27 14:45:00 → PIT 2026-11-27 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-11-27 19:40:00 → MDW 2026-11-27 20:10:00.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-04 17:25:00 → HOU 2026-12-04 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-04 20:45:00 → HOU 2026-12-04 23:00:00.

2026-11-27 → 2026-12-04 · $323.13

  • Southwest Airlines WN686 / WN3175: HOU 2026-11-27 07:45:00 → MDW 2026-11-27 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-11-27 07:45:00 → MSY 2026-11-27 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-11-27 10:10:00 → MDW 2026-11-27 12:30:00.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-04 17:25:00 → HOU 2026-12-04 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-04 20:45:00 → HOU 2026-12-04 23:00:00.

2026-11-27 → 2026-12-04 · $323.13

  • Southwest Airlines WN4547 / WN2348: HOU 2026-11-27 07:45:00 → MDW 2026-11-27 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
    • WN4547: HOU 2026-11-27 07:45:00 → SAT 2026-11-27 08:45:00; layover at SAT: 65 minutes.
    • WN2348: SAT 2026-11-27 09:50:00 → MDW 2026-11-27 12:20:00.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-04 17:25:00 → HOU 2026-12-04 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-04 20:45:00 → HOU 2026-12-04 23:00:00.

2026-11-27 → 2026-12-04 · $323.13

  • Southwest Airlines WN2211 / WN1718: HOU 2026-11-27 14:55:00 → MDW 2026-11-27 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2026-11-27 14:55:00 → CMH 2026-11-27 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2026-11-27 19:30:00 → MDW 2026-11-27 19:40:00.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-04 17:25:00 → HOU 2026-12-04 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-04 20:45:00 → HOU 2026-12-04 23:00:00.

2026-11-27 → 2026-12-04 · $333.25

  • Southwest Airlines WN2134: HOU 2026-11-27 17:15:00 → MDW 2026-11-27 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-04 17:25:00 → HOU 2026-12-04 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-04 20:45:00 → HOU 2026-12-04 23:00:00.

More dates for this route