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Houston → Chicago

Dec 4, 2026 · return Dec 13, 2026

HOU → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Fri, Dec 4 – Sun, Dec 13

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

Round-trip total · 1 adult · Taxes included

Fri, Dec 4 – 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

One-stop flights

Fri, Dec 4 – 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

Fri, Dec 4 – 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

Fri, Dec 4 – 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

Fri, Dec 4 – 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

Fri, Dec 4 – 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

Fri, Dec 4 – 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

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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Explore this route

All dates for this routeDec 3, 2026 → Dec 12, 2026Dec 5, 2026 → Dec 14, 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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-04 → 2026-12-13Southwest AirlinesWN1654 / WN4482$290.002026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Delta Air LinesDL1509 + DL1728 / DL2417 + DL2051$395.002026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Southwest AirlinesWN2134 / WN4482$290.002026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Southwest AirlinesWN2173 + WN287 / WN4482$282.502026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Southwest AirlinesWN686 + WN3175 / WN4482$282.502026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Southwest AirlinesWN4610 + WN3556 / WN4482$282.502026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Southwest AirlinesWN4547 + WN2348 / WN4482$282.502026-10-29T01:04:53Z
2026-12-04 → 2026-12-13Southwest AirlinesWN2211 + WN1718 / WN4482$282.502026-10-29T01:04:53Z

2026-12-04 → 2026-12-13 · $290.00

  • Southwest Airlines WN1654: HOU 2026-12-04 22:20:00 → MDW 2026-12-05 00:50:00; 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.

2026-12-04 → 2026-12-13 · $395.00

  • Delta Air Lines DL1509 / DL1728: HOU 2026-12-04 10:41:00 → MDW 2026-12-04 16:18:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
    • DL1509: HOU 2026-12-04 10:41:00 → ATL 2026-12-04 13:35:00; layover at ATL: 110 minutes.
    • DL1728: ATL 2026-12-04 15:25:00 → MDW 2026-12-04 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.

2026-12-04 → 2026-12-13 · $290.00

  • Southwest Airlines WN2134: HOU 2026-12-04 17:15:00 → MDW 2026-12-04 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.

2026-12-04 → 2026-12-13 · $282.50

  • Southwest Airlines WN2173 / WN287: HOU 2026-12-04 07:10:00 → MDW 2026-12-04 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN2173: HOU 2026-12-04 07:10:00 → STL 2026-12-04 09:10:00; layover at STL: 105 minutes.
    • WN287: STL 2026-12-04 10:55:00 → MDW 2026-12-04 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.

2026-12-04 → 2026-12-13 · $282.50

  • Southwest Airlines WN686 / WN3175: HOU 2026-12-04 07:45:00 → MDW 2026-12-04 12:30:00; 1 stop(s) via MSY; 285 minutes. Local airport times.
    • WN686: HOU 2026-12-04 07:45:00 → MSY 2026-12-04 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2026-12-04 10:10:00 → MDW 2026-12-04 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.

2026-12-04 → 2026-12-13 · $282.50

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

2026-12-04 → 2026-12-13 · $282.50

  • Southwest Airlines WN4547 / WN2348: HOU 2026-12-04 07:45:00 → MDW 2026-12-04 12:20:00; 1 stop(s) via SAT; 275 minutes. Local airport times.
    • WN4547: HOU 2026-12-04 07:45:00 → SAT 2026-12-04 08:45:00; layover at SAT: 65 minutes.
    • WN2348: SAT 2026-12-04 09:50:00 → MDW 2026-12-04 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.

2026-12-04 → 2026-12-13 · $282.50

  • Southwest Airlines WN2211 / WN1718: HOU 2026-12-04 14:55:00 → MDW 2026-12-04 19:40:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2211: HOU 2026-12-04 14:55:00 → CMH 2026-12-04 18:20:00; layover at CMH: 70 minutes.
    • WN1718: CMH 2026-12-04 19:30:00 → MDW 2026-12-04 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.

Explore this route

For AI assistants

  • This page: Houston (HOU) to Chicago (MDW) · Dec 4, 2026 · return Dec 13, 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 Search flights and hotels with your AI assistant · 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.