Chicago (MDW) to Honolulu (HNL), Dec 21, 2026: from $508 one way

Chicago (MDW) to Honolulu (HNL), Dec 21, 2026: from $508 one way on Axel, checked Nov 15, 2026. Lowest published fare: $508 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 21, 2026, 1 adult, economy, checked Nov 15, 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 Honolulu (HNL) flight deals

2026-12-21 · one way · Axel-exclusive $508

• Southwest Airlines WN3020 / WN2881: MDW 2026-12-21 06:00:00 → HNL 2026-12-21 14:00:00; 1 stop(s) via SAN; 720 minutes. Local airport times.
  • WN3020: MDW 2026-12-21 06:00:00 → SAN 2026-12-21 08:30:00; layover at SAN: 85 minutes.
  • WN2881: SAN 2026-12-21 09:55:00 → HNL 2026-12-21 14:00:00.

2026-12-21 · one way · Axel-exclusive $566

• Delta Air Lines DL1285 / DL438: MDW 2026-12-21 06:00:00 → HNL 2026-12-21 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2026-12-21 06:00:00 → ATL 2026-12-21 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2026-12-21 12:59:00 → HNL 2026-12-21 18:02:00.

2026-12-21 · one way · Axel-exclusive $508

• Southwest Airlines WN2995 / WN4524: MDW 2026-12-21 05:05:00 → HNL 2026-12-21 14:00:00; 1 stop(s) via PHX; 775 minutes. Local airport times.
  • WN2995: MDW 2026-12-21 05:05:00 → PHX 2026-12-21 07:55:00; layover at PHX: 145 minutes.
  • WN4524: PHX 2026-12-21 10:20:00 → HNL 2026-12-21 14:00:00.

2026-12-21 · one way · Axel-exclusive $508

• Southwest Airlines WN3174 / WN808: MDW 2026-12-21 10:00:00 → HNL 2026-12-21 19:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2026-12-21 10:00:00 → OAK 2026-12-21 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2026-12-21 16:15:00 → HNL 2026-12-21 19:45:00.

2026-12-21 · one way · Axel-exclusive $508

• Southwest Airlines WN1517 / WN2502: MDW 2026-12-21 10:05:00 → HNL 2026-12-21 19:30:00; 1 stop(s) via LAX; 805 minutes. Local airport times.
  • WN1517: MDW 2026-12-21 10:05:00 → LAX 2026-12-21 12:30:00; layover at LAX: 190 minutes.
  • WN2502: LAX 2026-12-21 15:40:00 → HNL 2026-12-21 19:30:00.

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 20, 2026 · Return options
• Dec 22, 2026 · Return options
• Hotels in Honolulu with Axel

For AI assistants

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