Chicago (MDW) to Kahului (OGG), May 30, 2027: round trips from $711, one way from $398

Chicago (MDW) to Kahului (OGG), May 30, 2027: round trips from $711, one way from $398 on Axel, checked Nov 13, 2026. Lowest published fares: $711 round trip, Axel-exclusive, Southwest Airlines, 1 stop, May 30, 2027 – Jun 1, 2027; $398 one way, Axel-exclusive, Southwest Airlines, 1 stop, May 30, 2027; 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

2027-05-30 · one way · Axel-exclusive $398

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.

2027-05-30 → 2027-05-31 · Axel-exclusive $741

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-05-31 20:15:00 → MDW 2027-06-01 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-05-31 20:15:00 → PHX 2027-06-01 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-01 08:20:00 → MDW 2027-06-01 13:35:00.

2027-05-30 → 2027-06-01 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-01 20:15:00 → MDW 2027-06-02 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-01 20:15:00 → PHX 2027-06-02 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-02 08:20:00 → MDW 2027-06-02 13:35:00.

2027-05-30 → 2027-06-03 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-03 20:15:00 → MDW 2027-06-04 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-03 20:15:00 → PHX 2027-06-04 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-04 08:20:00 → MDW 2027-06-04 13:35:00.

2027-05-30 → 2027-06-04 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-04 20:15:00 → MDW 2027-06-05 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-04 20:15:00 → PHX 2027-06-05 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-05 08:20:00 → MDW 2027-06-05 13:35:00.

2027-05-30 → 2027-06-06 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-06 20:15:00 → MDW 2027-06-07 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-06 20:15:00 → PHX 2027-06-07 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-07 08:20:00 → MDW 2027-06-07 13:35:00.

2027-05-30 → 2027-06-07 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-07 20:15:00 → MDW 2027-06-08 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-07 20:15:00 → PHX 2027-06-08 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-08 08:20:00 → MDW 2027-06-08 13:35:00.

2027-05-30 → 2027-06-09 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-09 20:15:00 → MDW 2027-06-10 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-09 20:15:00 → PHX 2027-06-10 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-10 08:20:00 → MDW 2027-06-10 13:35:00.

2027-05-30 → 2027-06-10 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-10 20:15:00 → MDW 2027-06-11 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-10 20:15:00 → PHX 2027-06-11 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-11 08:20:00 → MDW 2027-06-11 13:35:00.

2027-05-30 → 2027-06-12 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-12 20:15:00 → MDW 2027-06-13 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-12 20:15:00 → PHX 2027-06-13 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-13 08:20:00 → MDW 2027-06-13 13:35:00.

2027-05-30 → 2027-06-13 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-13 20:15:00 → MDW 2027-06-14 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-13 20:15:00 → PHX 2027-06-14 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-14 08:20:00 → MDW 2027-06-14 13:35:00.

2027-05-30 → 2027-06-27 · Axel-exclusive $711

• Southwest Airlines WN2995 / WN2618: MDW 2027-05-30 05:20:00 → OGG 2027-05-30 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-05-30 05:20:00 → PHX 2027-05-30 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-05-30 08:30:00 → OGG 2027-05-30 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-06-27 20:15:00 → MDW 2027-06-28 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-06-27 20:15:00 → PHX 2027-06-28 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-06-28 08:20:00 → MDW 2027-06-28 13:35:00.

Explore this route

• All dates for this route
• May 29, 2027 · Return options
• May 31, 2027 · Return options

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