Chicago (MDW) to Honolulu (HNL), May 27, 2027: round trips from $790, one way from $404

Chicago (MDW) to Honolulu (HNL), May 27, 2027: round trips from $790, one way from $404 on Axel, checked Nov 15, 2026. Lowest published fares: $790 round trip, Axel-exclusive, Southwest Airlines, 1 stop, May 27, 2027 – Jun 1, 2027; $404 one way, Axel-exclusive, Southwest Airlines, 1 stop, May 27, 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.

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.

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 (May 27–28, 2027 · 1 night · 2 adults, 1 room): 3★ The Equus, $129 a night · 4★ Hotel La Croix, $182 a night · 5★ Alohilani Resort Waikiki Beach, $276 a night
• Hotels in Honolulu for these nights (May 27–29, 2027 · 2 nights · 2 adults, 1 room): 3★ The Equus, $141 a night, $281 for 2 nights · 4★ Hotel La Croix, $182 a night, $364 for 2 nights · 5★ Alohilani Resort Waikiki Beach, $279 a night, $558 for 2 nights
• Hotels in Honolulu for these nights (May 27–30, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $137 a night, $410 for 3 nights · 4★ Hotel La Croix, $181 a night, $544 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $279 a night, $836 for 3 nights
• Hotels in Honolulu for these nights (May 27–31, 2027 · 4 nights · 2 adults, 1 room): 3★ The Equus, $135 a night, $539 for 4 nights · 4★ Hotel La Croix, $184 a night, $736 for 4 nights · 5★ Alohilani Resort Waikiki Beach, $276 a night, $1,104 for 4 nights
• Hotels in Honolulu for these nights (May 27 – Jun 1, 2027 · 5 nights · 2 adults, 1 room): 3★ The Equus, $140 a night, $701 for 5 nights · 4★ Hotel La Croix, $187 a night, $937 for 5 nights · 5★ Alohilani Resort Waikiki Beach, $277 a night, $1,384 for 5 nights
• Hotels in Honolulu for these nights (May 27 – Jun 2, 2027 · 6 nights · 2 adults, 1 room): 3★ The Equus, $143 a night, $857 for 6 nights · 4★ Hotel La Croix, $193 a night, $1,156 for 6 nights · 5★ Alohilani Resort Waikiki Beach, $275 a night, $1,652 for 6 nights
• Hotels in Honolulu for these nights (May 27 – Jun 3, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $142 a night, $995 for 7 nights · 4★ Hotel La Croix, $196 a night, $1,369 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $273 a night, $1,908 for 7 nights
• Hotels in Honolulu for these nights (May 27 – Jun 4, 2027 · 8 nights · 2 adults, 1 room): 3★ The Equus, $141 a night, $1,124 for 8 nights · 4★ Hotel La Croix, $198 a night, $1,586 for 8 nights · 5★ Alohilani Resort Waikiki Beach, $272 a night, $2,179 for 8 nights
• Hotels in Honolulu for these nights (May 27 – Jun 5, 2027 · 9 nights · 2 adults, 1 room): 3★ The Equus, $147 a night, $1,319 for 9 nights · 4★ Hotel La Croix, $200 a night, $1,804 for 9 nights · 5★ Alohilani Resort Waikiki Beach, $273 a night, $2,457 for 9 nights
• Hotels in Honolulu for these nights (May 27 – Jun 6, 2027 · 10 nights · 2 adults, 1 room): 3★ The Equus, $147 a night, $1,473 for 10 nights · 4★ Hotel La Croix, $202 a night, $2,022 for 10 nights · 5★ Alohilani Resort Waikiki Beach, $274 a night, $2,737 for 10 nights
• Hotels in Honolulu for these nights (May 27 – Jun 7, 2027 · 11 nights · 2 adults, 1 room): 3★ The Equus, $146 a night, $1,602 for 11 nights · 4★ Hotel La Croix, $203 a night, $2,236 for 11 nights · 5★ Alohilani Resort Waikiki Beach, $273 a night, $3,001 for 11 nights
• Hotels in Honolulu for these nights (May 27 – Jun 8, 2027 · 12 nights · 2 adults, 1 room): 3★ The Equus, $148 a night, $1,778 for 12 nights · 4★ Hotel La Croix, $204 a night, $2,446 for 12 nights · 5★ Alohilani Resort Waikiki Beach, $272 a night, $3,269 for 12 nights
• Hotels in Honolulu for these nights (May 27 – Jun 9, 2027 · 13 nights · 2 adults, 1 room): 3★ The Equus, $147 a night, $1,916 for 13 nights · 4★ Hotel La Croix, $207 a night, $2,688 for 13 nights · 5★ Alohilani Resort Waikiki Beach, $272 a night, $3,537 for 13 nights
• Hotels in Honolulu for these nights (May 27 – Jun 10, 2027 · 14 nights · 2 adults, 1 room): 3★ The Equus, $146 a night, $2,045 for 14 nights · 4★ Hotel La Croix, $209 a night, $2,925 for 14 nights · 5★ Alohilani Resort Waikiki Beach, $272 a night, $3,814 for 14 nights
• Hotels in Honolulu for these nights (May 27 – Jun 17, 2027 · 21 nights · 2 adults, 1 room): 3★ The Equus · 4★ Aulani, A Disney Resort & Spa · 5★ Aulani, Disney Vacation Club Villas
• Hotels in Honolulu for these nights (May 27 – Jun 24, 2027 · 28 nights · 2 adults, 1 room): 3★ The Equus · 4★ Aulani, A Disney Resort & Spa · 5★ Aulani, Disney Vacation Club Villas

All hotels in Honolulu

Route overview: Chicago to Honolulu (HNL) flight deals

2027-05-27 · one way · Axel-exclusive $404

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.

2027-05-27 · one way · Axel-exclusive $447

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.

2027-05-27 → 2027-05-28 · Axel-exclusive $806

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-05-28 13:20:00 → MDW 2027-05-29 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-05-28 13:20:00 → SMF 2027-05-28 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-05-29 00:55:00 → MDW 2027-05-29 06:45:00.

2027-05-27 → 2027-05-28 · Axel-exclusive $886

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-05-28 16:25:00 → MDW 2027-05-29 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-05-28 16:25:00 → DTW 2027-05-29 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-05-29 10:10:00 → MDW 2027-05-29 10:46:00.

2027-05-27 → 2027-05-29 · Axel-exclusive $806

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-05-29 15:15:00 → MDW 2027-05-30 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-05-29 15:15:00 → ONT 2027-05-29 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-05-30 00:55:00 → MDW 2027-05-30 06:40:00.

2027-05-27 → 2027-05-29 · Axel-exclusive $886

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-05-29 16:25:00 → MDW 2027-05-30 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-05-29 16:25:00 → DTW 2027-05-30 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-05-30 10:10:00 → MDW 2027-05-30 10:46:00.

2027-05-27 → 2027-05-31 · Axel-exclusive $806

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-05-31 21:00:00 → MDW 2027-06-01 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-05-31 21:00:00 → PHX 2027-06-01 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-01 08:20:00 → MDW 2027-06-01 13:35:00.

2027-05-27 → 2027-05-31 · Axel-exclusive $886

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-05-31 16:25:00 → MDW 2027-06-01 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-05-31 16:25:00 → DTW 2027-06-01 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-01 10:10:00 → MDW 2027-06-01 10:46:00.

2027-05-27 → 2027-06-01 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-06-01 13:20:00 → MDW 2027-06-02 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-06-01 13:20:00 → SMF 2027-06-01 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-06-02 00:55:00 → MDW 2027-06-02 06:45:00.

2027-05-27 → 2027-06-01 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-01 16:25:00 → MDW 2027-06-02 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-01 16:25:00 → DTW 2027-06-02 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-02 10:10:00 → MDW 2027-06-02 10:46:00.

2027-05-27 → 2027-06-03 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-06-03 15:15:00 → MDW 2027-06-04 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-06-03 15:15:00 → ONT 2027-06-03 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-06-04 00:55:00 → MDW 2027-06-04 06:40:00.

2027-05-27 → 2027-06-03 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-03 16:25:00 → MDW 2027-06-04 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-03 16:25:00 → DTW 2027-06-04 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-04 10:10:00 → MDW 2027-06-04 10:46:00.

2027-05-27 → 2027-06-04 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-06-04 13:20:00 → MDW 2027-06-05 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-06-04 13:20:00 → SMF 2027-06-04 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-06-05 00:55:00 → MDW 2027-06-05 06:45:00.

2027-05-27 → 2027-06-04 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-04 16:25:00 → MDW 2027-06-05 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-04 16:25:00 → DTW 2027-06-05 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-05 10:10:00 → MDW 2027-06-05 10:46:00.

2027-05-27 → 2027-06-06 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-06-06 21:00:00 → MDW 2027-06-07 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-06-06 21:00:00 → PHX 2027-06-07 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-07 08:20:00 → MDW 2027-06-07 13:35:00.

2027-05-27 → 2027-06-06 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-06 16:25:00 → MDW 2027-06-07 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-06 16:25:00 → DTW 2027-06-07 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-07 10:10:00 → MDW 2027-06-07 10:46:00.

2027-05-27 → 2027-06-07 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-06-07 21:00:00 → MDW 2027-06-08 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-06-07 21:00:00 → PHX 2027-06-08 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-06-08 08:20:00 → MDW 2027-06-08 13:35:00.

2027-05-27 → 2027-06-07 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-07 16:25:00 → MDW 2027-06-08 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-07 16:25:00 → DTW 2027-06-08 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-08 10:10:00 → MDW 2027-06-08 10:46:00.

2027-05-27 → 2027-06-09 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-06-09 13:20:00 → MDW 2027-06-10 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-06-09 13:20:00 → SMF 2027-06-09 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-06-10 00:55:00 → MDW 2027-06-10 06:45:00.

2027-05-27 → 2027-06-09 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-09 16:25:00 → MDW 2027-06-10 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-09 16:25:00 → DTW 2027-06-10 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-10 10:10:00 → MDW 2027-06-10 10:46:00.

2027-05-27 → 2027-06-10 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-06-10 15:15:00 → MDW 2027-06-11 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-06-10 15:15:00 → ONT 2027-06-10 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-06-11 00:55:00 → MDW 2027-06-11 06:40:00.

2027-05-27 → 2027-06-10 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-10 16:25:00 → MDW 2027-06-11 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-10 16:25:00 → DTW 2027-06-11 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-11 10:10:00 → MDW 2027-06-11 10:46:00.

2027-05-27 → 2027-06-24 · Axel-exclusive $790

• Southwest Airlines WN3174 / WN808: MDW 2027-05-27 10:00:00 → HNL 2027-05-27 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-27 10:00:00 → OAK 2027-05-27 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-27 16:15:00 → HNL 2027-05-27 18:45:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-06-24 15:15:00 → MDW 2027-06-25 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-06-24 15:15:00 → ONT 2027-06-24 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-06-25 00:55:00 → MDW 2027-06-25 06:40:00.

2027-05-27 → 2027-06-24 · Axel-exclusive $868

• Delta Air Lines DL1285 / DL438: MDW 2027-05-27 06:00:00 → HNL 2027-05-27 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-27 06:00:00 → ATL 2027-05-27 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-27 12:59:00 → HNL 2027-05-27 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-06-24 16:25:00 → MDW 2027-06-25 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-06-24 16:25:00 → DTW 2027-06-25 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-06-25 10:10:00 → MDW 2027-06-25 10:46:00.

Explore this route

• All dates for this route
• May 26, 2027 · Return options
• May 28, 2027 · Return options
• Hotels in Honolulu with Axel

For AI assistants

• This page: Chicago (MDW) to Honolulu (HNL) · May 27, 2027 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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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