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Houston → Chicago

Dec 7, 2026 · return Dec 13, 2026

HOU → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
5:15 pmHOU
2h 25m
Nonstop
7:40 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
8:40 pmHOU
2h 30m
Nonstop
11:10 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 7 – Sun, Dec 13

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

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
2:55 pmHOU
4h 45m
CMH · 1h 10m
7:40 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
7:45 amHOU
4h 35m
SAT · 1h 5m
12:20 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
7:10 amHOU
4h 55m
STL · 1h 45m
12:05 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
2:45 pmHOU
5h 25m
PIT · 1h 15m
8:10 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Sun, Dec 13

Southwest Airlines
7:45 amHOU
4h 45m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 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 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
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)
2026-12-07 → 2026-12-13Southwest AirlinesWN2134 / WN4482$290.002026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051$395.002026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2383 / WN4482$290.002026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2211 + WN1718 / WN4482$282.502026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Southwest AirlinesWN4547 + WN2348 / WN4482$282.502026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Southwest AirlinesWN2173 + WN287 / WN4482$282.502026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Southwest AirlinesWN4610 + WN3556 / WN4482$282.502026-10-29T01:04:53Z
2026-12-07 → 2026-12-13Southwest AirlinesWN686 + WN3175 / WN4482$282.502026-10-29T01:04:53Z

2026-12-07 → 2026-12-13 · $290.00

  • Southwest Airlines WN2134: HOU 2026-12-07 17:15:00 → MDW 2026-12-07 19:40:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $395.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-07 10:41:00 → MDW 2026-12-07 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-07 10:41:00 → ATL 2026-12-07 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-07 15:25:00 → MDW 2026-12-07 16:18:00.
  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-13 13:02:00 → HOU 2026-12-13 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-13 13:02:00 → ATL 2026-12-13 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-13 18:00:00 → HOU 2026-12-13 19:16:00.

2026-12-07 → 2026-12-13 · $290.00

  • Southwest Airlines WN2383: HOU 2026-12-07 20:40:00 → MDW 2026-12-07 23:10:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $282.50

  • Southwest Airlines WN2211 / WN1718: HOU 2026-12-07 14:55:00 → MDW 2026-12-07 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2026-12-07 14:55:00 → CMH 2026-12-07 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2026-12-07 19:30:00 → MDW 2026-12-07 19:40:00.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $282.50

  • Southwest Airlines WN4547 / WN2348: HOU 2026-12-07 07:45:00 → MDW 2026-12-07 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
    • WN4547: HOU 2026-12-07 07:45:00 → SAT 2026-12-07 08:45:00; layover at SAT: 65 minutes.
    • WN2348: SAT 2026-12-07 09:50:00 → MDW 2026-12-07 12:20:00.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $282.50

  • Southwest Airlines WN2173 / WN287: HOU 2026-12-07 07:10:00 → MDW 2026-12-07 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2173: HOU 2026-12-07 07:10:00 → STL 2026-12-07 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-12-07 10:55:00 → MDW 2026-12-07 12:05:00.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $282.50

  • Southwest Airlines WN4610 / WN3556: HOU 2026-12-07 14:45:00 → MDW 2026-12-07 20:10:00; 1 stop(s) via PIT; 325 minutes. Local airport times.
    • WN4610: HOU 2026-12-07 14:45:00 → PIT 2026-12-07 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2026-12-07 19:40:00 → MDW 2026-12-07 20:10:00.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

2026-12-07 → 2026-12-13 · $282.50

  • Southwest Airlines WN686 / WN3175: HOU 2026-12-07 07:45:00 → MDW 2026-12-07 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-07 07:45:00 → MSY 2026-12-07 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-07 10:10:00 → MDW 2026-12-07 12:30:00.
  • Southwest Airlines WN4482: MDW 2026-12-13 16:30:00 → HOU 2026-12-13 19:10:00; nonstop; 160 minutes. Local airport times.

More dates for this route