Chicago (MDW) to Kahului (OGG), Nov 29, 2026: round trips from $675, one way from $406

Chicago (MDW) to Kahului (OGG), Nov 29, 2026: round trips from $675, one way from $406 on Axel, checked Nov 13, 2026. Lowest published fares: $675 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 29–30, 2026; $406 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 29, 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

2026-11-29 · one way · Axel-exclusive $406

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.

2026-11-29 → 2026-11-30 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• 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.

2026-11-29 → 2026-12-01 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-01 20:15:00 → MDW 2026-12-02 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-01 20:15:00 → PHX 2026-12-02 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-02 08:20:00 → MDW 2026-12-02 12:35:00.

2026-11-29 → 2026-12-03 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• 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.

2026-11-29 → 2026-12-04 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-04 20:15:00 → MDW 2026-12-05 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-04 20:15:00 → PHX 2026-12-05 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-05 08:20:00 → MDW 2026-12-05 12:35:00.

2026-11-29 → 2026-12-06 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-06 20:15:00 → MDW 2026-12-07 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-06 20:15:00 → PHX 2026-12-07 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-07 08:20:00 → MDW 2026-12-07 12:35:00.

2026-11-29 → 2026-12-07 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-07 20:15:00 → MDW 2026-12-08 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-07 20:15:00 → PHX 2026-12-08 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-08 08:20:00 → MDW 2026-12-08 12:35:00.

2026-11-29 → 2026-12-09 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-09 20:15:00 → MDW 2026-12-10 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-09 20:15:00 → PHX 2026-12-10 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-10 08:20:00 → MDW 2026-12-10 12:35:00.

2026-11-29 → 2026-12-10 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-10 20:15:00 → MDW 2026-12-11 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-10 20:15:00 → PHX 2026-12-11 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-11 08:20:00 → MDW 2026-12-11 12:35:00.

2026-11-29 → 2026-12-12 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-12 20:15:00 → MDW 2026-12-13 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-12 20:15:00 → PHX 2026-12-13 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-13 08:20:00 → MDW 2026-12-13 12:35:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $675

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2026-12-13 20:15:00 → MDW 2026-12-14 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2026-12-13 20:15:00 → PHX 2026-12-14 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2026-12-14 08:20:00 → MDW 2026-12-14 12:35:00.

2026-11-29 → 2026-12-27 · Axel-exclusive $810

• Southwest Airlines WN3020 / WN3157: MDW 2026-11-29 06:00:00 → OGG 2026-11-29 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-11-29 06:00:00 → SAN 2026-11-29 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-11-29 10:55:00 → OGG 2026-11-29 14:40:00.
• 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.

Explore this route

• All dates for this route
• Nov 28, 2026 · Return options
• Nov 30, 2026 · Return options

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