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Chicago → Houston

Dec 30, 2026 · return Jan 2, 2027

MDW → HOU1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
4:30 pmMDW
2h 40m
Nonstop
7:10 pmHOU
Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
10:15 amMDW
2h 35m
Nonstop
12:50 pmHOU
Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 30 – Sat, Jan 2

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

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
5:00 pmMDW
2h 45m
Nonstop
7:45 pmHOU
Southwest Airlines
2:55 pmHOU
4h 45m
CMH · 1h 10m
7:40 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
7:35 amMDW
5h 50m
MCI · 2h 10m
1:25 pmHOU
Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
11:30 amMDW
5h 35m
STL · 2h 15m
5:05 pmHOU
Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
7:40 amMDW
5h 50m
CLT · 1h 10m
1:30 pmHOU
Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 30 – Sat, Jan 2

Southwest Airlines
5:25 pmMDW
5h 35m
BNA · 1h 55m
11:00 pmHOU
Southwest Airlines
10:20 pmHOU
2h 30m
Nonstop
12:50 am+1MDW

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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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)
2026-12-30 → 2027-01-02Southwest AirlinesWN4482 / WN1654$342.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Delta Air LinesDL2417 + DL2051 / DL1509 + DL1728$420.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Southwest AirlinesWN4395 / WN1654$342.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Southwest AirlinesWN4482 / WN2211 + WN1718$336.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Southwest AirlinesWN2959 + WN2672 / WN1654$336.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Southwest AirlinesWN2737 + WN4624 / WN1654$336.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Southwest AirlinesWN2912 + WN998 / WN1654$336.002026-10-29T01:29:08Z
2026-12-30 → 2027-01-02Southwest AirlinesWN2897 + WN1530 / WN1654$336.002026-10-29T01:29:08Z

2026-12-30 → 2027-01-02 · $342.00

  • Southwest Airlines WN4482: MDW 2026-12-30 16:30:00 → HOU 2026-12-30 19:10:00; nonstop; 160 minutes. Local airport times.
  • Southwest Airlines WN1654: HOU 2027-01-02 22:20:00 → MDW 2027-01-03 00:50:00; nonstop; 150 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $420.00

  • Delta Air Lines DL2417 / DL2051: MDW 2026-12-30 13:02:00 → HOU 2026-12-30 19:16:00; 1 stop(s) via ATL; 374 minutes. Local airport times.
    • DL2417: MDW 2026-12-30 13:02:00 → ATL 2026-12-30 16:01:00; layover at ATL: 119 minutes.
    • DL2051: ATL 2026-12-30 18:00:00 → HOU 2026-12-30 19:16:00.
  • Delta Air Lines DL1509 / DL1728: HOU 2027-01-02 10:41:00 → MDW 2027-01-02 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2027-01-02 10:41:00 → ATL 2027-01-02 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2027-01-02 15:25:00 → MDW 2027-01-02 16:18:00.

2026-12-30 → 2027-01-02 · $342.00

  • Southwest Airlines WN4395: MDW 2026-12-30 10:15:00 → HOU 2026-12-30 12:50:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN1654: HOU 2027-01-02 22:20:00 → MDW 2027-01-03 00:50:00; nonstop; 150 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $336.00

  • Southwest Airlines WN4482: MDW 2026-12-30 17:00:00 → HOU 2026-12-30 19:45:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2211 / WN1718: HOU 2027-01-02 14:55:00 → MDW 2027-01-02 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2027-01-02 14:55:00 → CMH 2027-01-02 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2027-01-02 19:30:00 → MDW 2027-01-02 19:40:00.

2026-12-30 → 2027-01-02 · $336.00

  • Southwest Airlines WN2959 / WN2672: MDW 2026-12-30 07:35:00 → HOU 2026-12-30 13:25:00; 1 stop(s) via MCI; 350 minutes. Local airport times.
    • WN2959: MDW 2026-12-30 07:35:00 → MCI 2026-12-30 09:05:00; layover at MCI: 130 minutes.
    • WN2672: MCI 2026-12-30 11:15:00 → HOU 2026-12-30 13:25:00.
  • Southwest Airlines WN1654: HOU 2027-01-02 22:20:00 → MDW 2027-01-03 00:50:00; nonstop; 150 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $336.00

  • Southwest Airlines WN2737 / WN4624: MDW 2026-12-30 11:30:00 → HOU 2026-12-30 17:05:00; 1 stop(s) via STL; 335 minutes. Local airport times.
    • WN2737: MDW 2026-12-30 11:30:00 → STL 2026-12-30 12:40:00; layover at STL: 135 minutes.
    • WN4624: STL 2026-12-30 14:55:00 → HOU 2026-12-30 17:05:00.
  • Southwest Airlines WN1654: HOU 2027-01-02 22:20:00 → MDW 2027-01-03 00:50:00; nonstop; 150 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $336.00

  • Southwest Airlines WN2912 / WN998: MDW 2026-12-30 07:40:00 → HOU 2026-12-30 13:30:00; 1 stop(s) via CLT; 350 minutes. Local airport times.
    • WN2912: MDW 2026-12-30 07:40:00 → CLT 2026-12-30 10:35:00; layover at CLT: 70 minutes.
    • WN998: CLT 2026-12-30 11:45:00 → HOU 2026-12-30 13:30:00.
  • Southwest Airlines WN1654: HOU 2027-01-02 22:20:00 → MDW 2027-01-03 00:50:00; nonstop; 150 minutes. Local airport times.

2026-12-30 → 2027-01-02 · $336.00

  • Southwest Airlines WN2897 / WN1530: MDW 2026-12-30 17:25:00 → HOU 2026-12-30 23:00:00; 1 stop(s) via BNA; 335 minutes. Local airport times.
    • WN2897: MDW 2026-12-30 17:25:00 → BNA 2026-12-30 18:50:00; layover at BNA: 115 minutes.
    • WN1530: BNA 2026-12-30 20:45:00 → HOU 2026-12-30 23:00:00.
  • Southwest Airlines WN1654: HOU 2027-01-02 22:20:00 → MDW 2027-01-03 00:50:00; nonstop; 150 minutes. Local airport times.

More dates for this route