Chicago (MDW) to Kahului (OGG), Nov 19, 2026: round trips from $600, one way from $325

Chicago (MDW) to Kahului (OGG), Nov 19, 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, Nov 19–20, 2026; $325 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 19, 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.

Route overview: Chicago to Kahului (OGG) flight deals

2026-11-19 · one way · Axel-exclusive $325

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.

2026-11-19 → 2026-11-20 · Axel-exclusive $600

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-11-20 20:15:00 → MDW 2026-11-21 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-11-20 20:15:00 → PHX 2026-11-21 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-11-21 08:20:00 → MDW 2026-11-21 12:35:00.

2026-11-19 → 2026-11-21 · Axel-exclusive $675

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3263 / WN3895: OGG 2026-11-21 14:25:00 → MDW 2026-11-22 05:00:00; 1 stop(s) via SJC; 635 minutes. Local airport times.
  • WN3263: OGG 2026-11-21 14:25:00 → SJC 2026-11-21 21:25:00; layover at SJC: 95 minutes.
  • WN3895: SJC 2026-11-21 23:00:00 → MDW 2026-11-22 05:00:00.

2026-11-19 → 2026-11-23 · Axel-exclusive $675

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3263 / WN3895: OGG 2026-11-23 14:25:00 → MDW 2026-11-24 05:00:00; 1 stop(s) via SJC; 635 minutes. Local airport times.
  • WN3263: OGG 2026-11-23 14:25:00 → SJC 2026-11-23 21:25:00; layover at SJC: 95 minutes.
  • WN3895: SJC 2026-11-23 23:00:00 → MDW 2026-11-24 05:00:00.

2026-11-19 → 2026-11-24 · Axel-exclusive $675

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3260 / WN2871: OGG 2026-11-24 22:30:00 → MDW 2026-11-25 12:30:00; 1 stop(s) via OAK; 600 minutes. Local airport times.
  • WN3260: OGG 2026-11-24 22:30:00 → OAK 2026-11-25 05:30:00; layover at OAK: 60 minutes.
  • WN2871: OAK 2026-11-25 06:30:00 → MDW 2026-11-25 12:30:00.

2026-11-19 → 2026-11-26 · Axel-exclusive $675

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-11-26 20:15:00 → MDW 2026-11-27 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-11-26 20:15:00 → PHX 2026-11-27 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-11-27 08:20:00 → MDW 2026-11-27 12:35:00.

2026-11-19 → 2026-11-27 · Axel-exclusive $675

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-11-27 20:15:00 → MDW 2026-11-28 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-11-27 20:15:00 → PHX 2026-11-28 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-11-28 08:20:00 → MDW 2026-11-28 12:35:00.

2026-11-19 → 2026-11-29 · Axel-exclusive $675

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-11-29 20:15:00 → MDW 2026-11-30 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-11-29 20:15:00 → PHX 2026-11-30 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-11-30 08:20:00 → MDW 2026-11-30 12:35:00.

2026-11-19 → 2026-11-30 · Axel-exclusive $600

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3263 / WN3895: OGG 2026-11-30 14:25:00 → MDW 2026-12-01 05:00:00; 1 stop(s) via SJC; 635 minutes. Local airport times.
  • WN3263: OGG 2026-11-30 14:25:00 → SJC 2026-11-30 21:25:00; layover at SJC: 95 minutes.
  • WN3895: SJC 2026-11-30 23:00:00 → MDW 2026-12-01 05:00:00.

2026-11-19 → 2026-12-02 · Axel-exclusive $600

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-02 20:15:00 → MDW 2026-12-03 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-02 20:15:00 → PHX 2026-12-03 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-03 08:20:00 → MDW 2026-12-03 12:35:00.

2026-11-19 → 2026-12-03 · Axel-exclusive $600

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-03 20:15:00 → MDW 2026-12-04 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-03 20:15:00 → PHX 2026-12-04 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-04 08:20:00 → MDW 2026-12-04 12:35:00.

2026-11-19 → 2026-12-17 · Axel-exclusive $600

• Southwest Airlines WN2691 / WN1593: MDW 2026-11-19 05:50:00 → OGG 2026-11-19 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-11-19 05:50:00 → LAS 2026-11-19 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-11-19 09:00:00 → OGG 2026-11-19 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-17 20:15:00 → MDW 2026-12-18 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-17 20:15:00 → PHX 2026-12-18 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-18 08:20:00 → MDW 2026-12-18 12:35:00.

Explore this route

• All dates for this route
• Nov 18, 2026 · Return options
• Nov 20, 2026 · Return options

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