Chicago (MDW) to Kahului (OGG), Dec 26, 2026 – Jan 3, 2027: from $870 round trip

Chicago (MDW) to Kahului (OGG), Dec 26, 2026 – Jan 3, 2027: from $870 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $870 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 26, 2026 – Jan 3, 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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to Kahului (OGG) flight deals

2026-12-26 → 2027-01-03 · Axel-exclusive $870

• Southwest Airlines WN2995 / WN2618: MDW 2026-12-26 05:20:00 → OGG 2026-12-26 12:55:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN2995: MDW 2026-12-26 05:20:00 → PHX 2026-12-26 08:10:00; layover at PHX: 80 minutes.
  • WN2618: PHX 2026-12-26 09:30:00 → OGG 2026-12-26 12:55:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-01-03 20:15:00 → MDW 2027-01-04 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-01-03 20:15:00 → PHX 2027-01-04 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-01-04 08:20:00 → MDW 2027-01-04 12:35:00.

2026-12-26 → 2027-01-03 · Axel-exclusive $870

• Southwest Airlines WN2691 / WN1593: MDW 2026-12-26 05:50:00 → OGG 2026-12-26 13:10:00; 1 stop(s) via LAS; 680 minutes. Local airport times.
  • WN2691: MDW 2026-12-26 05:50:00 → LAS 2026-12-26 07:45:00; layover at LAS: 75 minutes.
  • WN1593: LAS 2026-12-26 09:00:00 → OGG 2026-12-26 13:10:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-01-03 20:15:00 → MDW 2027-01-04 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-01-03 20:15:00 → PHX 2027-01-04 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-01-04 08:20:00 → MDW 2027-01-04 12:35:00.

2026-12-26 → 2027-01-03 · Axel-exclusive $870

• Southwest Airlines WN3020 / WN3157: MDW 2026-12-26 06:00:00 → OGG 2026-12-26 14:40:00; 1 stop(s) via SAN; 760 minutes. Local airport times.
  • WN3020: MDW 2026-12-26 06:00:00 → SAN 2026-12-26 08:30:00; layover at SAN: 145 minutes.
  • WN3157: SAN 2026-12-26 10:55:00 → OGG 2026-12-26 14:40:00.
• Southwest Airlines WN3261 / WN3443: OGG 2027-01-03 20:15:00 → MDW 2027-01-04 12:35:00; 1 stop(s) via PHX; 740 minutes. Local airport times.
  • WN3261: OGG 2027-01-03 20:15:00 → PHX 2027-01-04 05:05:00; layover at PHX: 195 minutes.
  • WN3443: PHX 2027-01-04 08:20:00 → MDW 2027-01-04 12:35:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Dec 25, 2026 · Return options
• Dec 27, 2026 · Return options

For AI assistants

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