Chicago (MDW) to Kahului (OGG), Sep 13, 2027: round trips from $612, one way from $329

Chicago (MDW) to Kahului (OGG), Sep 13, 2027: round trips from $612, one way from $329 on Axel, checked Nov 13, 2026. Lowest published fares: $612 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Sep 13–14, 2027; $329 one way, Axel-exclusive, Southwest Airlines, 1 stop, Sep 13, 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

2027-09-13 · one way · Axel-exclusive $329

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

2027-09-13 → 2027-09-14 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-14 20:15:00 → MDW 2027-09-15 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-14 20:15:00 → PHX 2027-09-15 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-15 08:20:00 → MDW 2027-09-15 13:35:00.

2027-09-13 → 2027-09-15 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-15 20:15:00 → MDW 2027-09-16 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-15 20:15:00 → PHX 2027-09-16 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-16 08:20:00 → MDW 2027-09-16 13:35:00.

2027-09-13 → 2027-09-16 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-16 20:15:00 → MDW 2027-09-17 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-16 20:15:00 → PHX 2027-09-17 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-17 08:20:00 → MDW 2027-09-17 13:35:00.

2027-09-13 → 2027-09-18 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-18 20:15:00 → MDW 2027-09-19 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-18 20:15:00 → PHX 2027-09-19 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-19 08:20:00 → MDW 2027-09-19 13:35:00.

2027-09-13 → 2027-09-19 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-19 20:15:00 → MDW 2027-09-20 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-19 20:15:00 → PHX 2027-09-20 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-20 08:20:00 → MDW 2027-09-20 13:35:00.

2027-09-13 → 2027-09-21 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-21 20:15:00 → MDW 2027-09-22 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-21 20:15:00 → PHX 2027-09-22 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-22 08:20:00 → MDW 2027-09-22 13:35:00.

2027-09-13 → 2027-09-22 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-22 20:15:00 → MDW 2027-09-23 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-22 20:15:00 → PHX 2027-09-23 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-23 08:20:00 → MDW 2027-09-23 13:35:00.

2027-09-13 → 2027-09-23 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-23 20:15:00 → MDW 2027-09-24 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-23 20:15:00 → PHX 2027-09-24 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-24 08:20:00 → MDW 2027-09-24 13:35:00.

2027-09-13 → 2027-09-25 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-25 20:15:00 → MDW 2027-09-26 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-25 20:15:00 → PHX 2027-09-26 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-26 08:20:00 → MDW 2027-09-26 13:35:00.

2027-09-13 → 2027-09-26 · Axel-exclusive $612

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-09-26 20:15:00 → MDW 2027-09-27 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-09-26 20:15:00 → PHX 2027-09-27 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-09-27 08:20:00 → MDW 2027-09-27 13:35:00.

2027-09-13 → 2027-10-04 · Axel-exclusive $629

• Southwest Airlines WN2995 / WN2618: MDW 2027-09-13 05:20:00 → OGG 2027-09-13 11:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2027-09-13 05:20:00 → PHX 2027-09-13 07:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2027-09-13 08:30:00 → OGG 2027-09-13 11:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-10-04 20:15:00 → MDW 2027-10-05 13:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-10-04 20:15:00 → PHX 2027-10-05 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-10-05 08:20:00 → MDW 2027-10-05 13:35:00.

Explore this route

• All dates for this route
• Sep 12, 2027 · Return options
• Sep 14, 2027 · Return options

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