Chicago (MDW) to Honolulu (HNL), Jun 8–20, 2027: from $810 round trip

Chicago (MDW) to Honolulu (HNL), Jun 8–20, 2027: from $810 round trip on Axel, checked Nov 15, 2026. Lowest published fare: $810 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jun 8–20, 2027, 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.

Hotels in Honolulu for these trips

Hotels: under a trip, hotels in Honolulu for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Honolulu for these nights (Jun 8–20, 2027 · 12 nights · 2 adults, 1 room): 3★ The Equus, $146 a night, $1,755 for 12 nights · 4★ Aston Waikiki Sunset, $222 a night, $2,667 for 12 nights · 5★ Alohilani Resort Waikiki Beach, $281 a night, $3,371 for 12 nights

All hotels in Honolulu

Route overview: Chicago to Honolulu (HNL) flight deals

2027-06-08 → 2027-06-20 · Axel-exclusive $810

• Southwest Airlines WN3020 / WN2881: MDW 2027-06-08 06:00:00 → HNL 2027-06-08 13:00:00; 1 stop(s) via SAN; 720 minutes. Local airport times.
  • WN3020: MDW 2027-06-08 06:00:00 → SAN 2027-06-08 08:30:00; layover at SAN: 85 minutes.
  • WN2881: SAN 2027-06-08 09:55:00 → HNL 2027-06-08 13:00:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-06-20 21:00:00 → MDW 2027-06-21 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-06-20 21:00:00 → PHX 2027-06-21 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-21 08:20:00 → MDW 2027-06-21 13:35:00.

2027-06-08 → 2027-06-20 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-06-08 06:00:00 → HNL 2027-06-08 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-06-08 06:00:00 → ATL 2027-06-08 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-06-08 12:59:00 → HNL 2027-06-08 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-20 16:25:00 → MDW 2027-06-21 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-20 16:25:00 → DTW 2027-06-21 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-21 10:10:00 → MDW 2027-06-21 10:46:00.

2027-06-08 → 2027-06-20 · Axel-exclusive $810

• Southwest Airlines WN1517 / WN2502: MDW 2027-06-08 10:05:00 → HNL 2027-06-08 18:30:00; 1 stop(s) via LAX; 805 minutes. Local airport times.
  • WN1517: MDW 2027-06-08 10:05:00 → LAX 2027-06-08 12:30:00; layover at LAX: 190 minutes.
  • WN2502: LAX 2027-06-08 15:40:00 → HNL 2027-06-08 18:30:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-06-20 21:00:00 → MDW 2027-06-21 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-06-20 21:00:00 → PHX 2027-06-21 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-21 08:20:00 → MDW 2027-06-21 13:35:00.

2027-06-08 → 2027-06-20 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-06-08 10:00:00 → HNL 2027-06-08 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-06-08 10:00:00 → OAK 2027-06-08 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-06-08 16:15:00 → HNL 2027-06-08 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-06-20 21:00:00 → MDW 2027-06-21 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-06-20 21:00:00 → PHX 2027-06-21 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-21 08:20:00 → MDW 2027-06-21 13:35:00.

2027-06-08 → 2027-06-20 · Axel-exclusive $810

• Southwest Airlines WN2995 / WN4524: MDW 2027-06-08 05:05:00 → HNL 2027-06-08 13:00:00; 1 stop(s) via PHX; 775 minutes. Local airport times.
  • WN2995: MDW 2027-06-08 05:05:00 → PHX 2027-06-08 06:55:00; layover at PHX: 145 minutes.
  • WN4524: PHX 2027-06-08 09:20:00 → HNL 2027-06-08 13:00:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-06-20 21:00:00 → MDW 2027-06-21 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-06-20 21:00:00 → PHX 2027-06-21 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-21 08:20:00 → MDW 2027-06-21 13:35:00.

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
• Jun 7, 2027 · Return options
• Jun 9, 2027 · Return options
• Hotels in Honolulu with Axel

For AI assistants

• This page: Chicago (MDW) to Honolulu (HNL) · Jun 8, 2027 · return Jun 20, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Honolulu for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Honolulu (HNL) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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