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Route overview: Chicago to Kahului (OGG) flight deals

Chicago (MDW) to Kahului (OGG), Dec 17, 2026: round trips from $600, one way from $325

Chicago (MDW) to Kahului (OGG), Dec 17, 2026: round trips from $600, one way from $325 on Axel, checked Nov 13, 2026. Lowest published fares: $600 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 17–18, 2026; $325 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 17, 2026; 1 adult, economy, checked Nov 13, 2026.

MDW → OGG1 adulteconomyOne way and round trips

17 flight options · 1 airline

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

December 2026

Flights for your trip

  1. Thu, Dec 17 · One way

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG

    Example one-way total $325 · 1 adult · Taxes included

  2. Thu, Dec 17 – Fri, Dec 18

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $600 · 1 adult · Taxes included

  3. Thu, Dec 17 – Sat, Dec 19

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  4. Thu, Dec 17 – Mon, Dec 21

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  5. Thu, Dec 17 – Tue, Dec 22

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  6. Thu, Dec 17 – Thu, Dec 24

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  7. Thu, Dec 17 – Fri, Dec 25

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  8. Thu, Dec 17 – Sun, Dec 27

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  9. Thu, Dec 17 – Mon, Dec 28

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  10. Thu, Dec 17 – Wed, Dec 30

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  11. Thu, Dec 17 – Thu, Dec 31

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $735 · 1 adult · Taxes included

  12. Thu, Dec 17 – Thu, Jan 14

    Southwest Airlines
    5:20 amMDW
    11h 35m
    PHX · 1h 20m
    12:55 pmOGG
    Southwest Airlines
    8:15 pmOGG
    12h 20m
    PHX · 3h 15m
    12:35 pm+1MDW

    Example round-trip total $600 · 1 adult · Taxes included

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MDW ⇄ OGG

Economy

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Explore this route

For AI assistants: every fare, every link, instructions

Chicago (MDW) to Kahului (OGG), Dec 17, 2026: round trips from $600, one way from $325 on Axel, checked Nov 13, 2026. Lowest published fares: $600 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 17–18, 2026; $325 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 17, 2026; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice checked
2026-12-17 · one waySouthwest AirlinesWN2995 + WN261805:20:00→12:55:00 11h 35m 1 stop via PHXAxel-exclusive $325Nov 13, 2026
2026-12-17 → 2026-12-18Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $600Nov 13, 2026
2026-12-17 → 2026-12-19Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-20Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-21Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-22Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-23Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-24Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-25Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-26Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-27Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-28Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-29Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-30Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2026-12-31Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $735Nov 13, 2026
2026-12-17 → 2027-01-07Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $600Nov 13, 2026
2026-12-17 → 2027-01-14Southwest AirlinesWN2995 + WN2618 / WN3261 + WN344305:20:00→12:55:00 11h 35m 1 stop via PHX · 20:15:00→12:35:00 12h 20m 1 stop via PHXAxel-exclusive $600Nov 13, 2026

Route overview: Chicago to Kahului (OGG) flight deals

2026-12-17 · one way · Axel-exclusive $325

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.

2026-12-17 → 2026-12-18 · Axel-exclusive $600

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-18 20:15:00 → MDW 2026-12-19 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-18 20:15:00 → PHX 2026-12-19 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-19 08:20:00 → MDW 2026-12-19 12:35:00.

2026-12-17 → 2026-12-19 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-19 20:15:00 → MDW 2026-12-20 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-19 20:15:00 → PHX 2026-12-20 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-20 08:20:00 → MDW 2026-12-20 12:35:00.

2026-12-17 → 2026-12-21 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-21 20:15:00 → MDW 2026-12-22 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-21 20:15:00 → PHX 2026-12-22 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-22 08:20:00 → MDW 2026-12-22 12:35:00.

2026-12-17 → 2026-12-22 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-22 20:15:00 → MDW 2026-12-23 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-22 20:15:00 → PHX 2026-12-23 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-23 08:20:00 → MDW 2026-12-23 12:35:00.

2026-12-17 → 2026-12-24 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-24 20:15:00 → MDW 2026-12-25 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-24 20:15:00 → PHX 2026-12-25 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-25 08:20:00 → MDW 2026-12-25 12:35:00.

2026-12-17 → 2026-12-25 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-25 20:15:00 → MDW 2026-12-26 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-25 20:15:00 → PHX 2026-12-26 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-26 08:20:00 → MDW 2026-12-26 12:35:00.

2026-12-17 → 2026-12-27 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-27 20:15:00 → MDW 2026-12-28 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-27 20:15:00 → PHX 2026-12-28 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-28 08:20:00 → MDW 2026-12-28 12:35:00.

2026-12-17 → 2026-12-28 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-28 20:15:00 → MDW 2026-12-29 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-28 20:15:00 → PHX 2026-12-29 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-29 08:20:00 → MDW 2026-12-29 12:35:00.

2026-12-17 → 2026-12-30 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-30 20:15:00 → MDW 2026-12-31 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-30 20:15:00 → PHX 2026-12-31 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2026-12-31 08:20:00 → MDW 2026-12-31 12:35:00.

2026-12-17 → 2026-12-31 · Axel-exclusive $735

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2026-12-31 20:15:00 → MDW 2027-01-01 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2026-12-31 20:15:00 → PHX 2027-01-01 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2027-01-01 08:20:00 → MDW 2027-01-01 12:35:00.

2026-12-17 → 2027-01-14 · Axel-exclusive $600

  • Southwest Airlines WN2995 / WN2618: MDW 2026-12-17 05:20:00 → OGG 2026-12-17 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
    • WN2995: MDW 2026-12-17 05:20:00 → PHX 2026-12-17 08:10:00; layover at PHX: 80 minutes.
    • WN2618: PHX 2026-12-17 09:30:00 → OGG 2026-12-17 12:55:00.
  • Southwest Airlines WN3261 / WN3443: OGG 2027-01-14 20:15:00 → MDW 2027-01-15 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
    • WN3261: OGG 2027-01-14 20:15:00 → PHX 2027-01-15 05:05:00; layover at PHX: 195 minutes.
    • WN3443: PHX 2027-01-15 08:20:00 → MDW 2027-01-15 12:35:00.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to Kahului (OGG) · Dec 17, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date.
  • Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
  • 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 Chicago to Kahului (OGG) flight deals · 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.