Chicago (MDW) to Honolulu (HNL), Aug 16, 2027: round trips from $770, one way from $425

Chicago (MDW) to Honolulu (HNL), Aug 16, 2027: round trips from $770, one way from $425 on Axel, checked Nov 15, 2026. Lowest published fares: $770 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Aug 16, 2027 – Sep 13, 2027; $425 one way, Axel-exclusive, Southwest Airlines, 1 stop, Aug 16, 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 (Aug 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $161 a night · 4★ Queen Kapiolani Hotel, $202 a night · 5★ Alohilani Resort Waikiki Beach, $255 a night
• Hotels in Honolulu for these nights (Aug 16–18, 2027 · 2 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $160 a night, $320 for 2 nights · 4★ Queen Kapiolani Hotel, $203 a night, $405 for 2 nights · 5★ Alohilani Resort Waikiki Beach, $258 a night, $516 for 2 nights
• Hotels in Honolulu for these nights (Aug 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $160 a night, $480 for 3 nights · 4★ Queen Kapiolani Hotel, $203 a night, $609 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $256 a night, $768 for 3 nights
• Hotels in Honolulu for these nights (Aug 16–20, 2027 · 4 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $161 a night, $644 for 4 nights · 4★ Queen Kapiolani Hotel, $207 a night, $827 for 4 nights · 5★ Alohilani Resort Waikiki Beach, $255 a night, $1,021 for 4 nights
• Hotels in Honolulu for these nights (Aug 16–21, 2027 · 5 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $162 a night, $809 for 5 nights · 4★ Hotel La Croix, $206 a night, $1,030 for 5 nights · 5★ Alohilani Resort Waikiki Beach, $257 a night, $1,285 for 5 nights
• Hotels in Honolulu for these nights (Aug 16–22, 2027 · 6 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $162 a night, $970 for 6 nights · 4★ Hotel La Croix, $206 a night, $1,238 for 6 nights · 5★ Alohilani Resort Waikiki Beach, $258 a night, $1,549 for 6 nights
• Hotels in Honolulu for these nights (Aug 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $159 a night, $1,113 for 7 nights · 4★ Hotel La Croix, $207 a night, $1,452 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $260 a night, $1,817 for 7 nights
• Hotels in Honolulu for these nights (Aug 16–24, 2027 · 8 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $157 a night, $1,258 for 8 nights · 4★ Hotel La Croix, $208 a night, $1,666 for 8 nights · 5★ Alohilani Resort Waikiki Beach, $260 a night, $2,081 for 8 nights
• Hotels in Honolulu for these nights (Aug 16–25, 2027 · 9 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $156 a night, $1,403 for 9 nights · 4★ Hotel La Croix, $208 a night, $1,872 for 9 nights · 5★ Alohilani Resort Waikiki Beach, $262 a night, $2,354 for 9 nights
• Hotels in Honolulu for these nights (Aug 16–26, 2027 · 10 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $155 a night, $1,547 for 10 nights · 4★ Hotel La Croix, $208 a night, $2,081 for 10 nights · 5★ Alohilani Resort Waikiki Beach, $262 a night, $2,622 for 10 nights
• Hotels in Honolulu for these nights (Aug 16–27, 2027 · 11 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 (Aug 16–28, 2027 · 12 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 (Aug 16–29, 2027 · 13 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 (Aug 16–30, 2027 · 14 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 (Aug 16 – Sep 6, 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 (Aug 16 – Sep 13, 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

2027-08-16 · one way · Axel-exclusive $425

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.

2027-08-16 · one way · Axel-exclusive $470

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.

2027-08-16 → 2027-08-17 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-08-17 13:20:00 → MDW 2027-08-18 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-08-17 13:20:00 → SMF 2027-08-17 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-08-18 00:55:00 → MDW 2027-08-18 06:45:00.

2027-08-16 → 2027-08-17 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-17 16:25:00 → MDW 2027-08-18 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-17 16:25:00 → DTW 2027-08-18 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-18 10:10:00 → MDW 2027-08-18 10:46:00.

2027-08-16 → 2027-08-18 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-08-18 13:20:00 → MDW 2027-08-19 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-08-18 13:20:00 → SMF 2027-08-18 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-08-19 00:55:00 → MDW 2027-08-19 06:45:00.

2027-08-16 → 2027-08-18 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-18 16:25:00 → MDW 2027-08-19 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-18 16:25:00 → DTW 2027-08-19 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-19 10:10:00 → MDW 2027-08-19 10:46:00.

2027-08-16 → 2027-08-20 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-08-20 13:20:00 → MDW 2027-08-21 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-08-20 13:20:00 → SMF 2027-08-20 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-08-21 00:55:00 → MDW 2027-08-21 06:45:00.

2027-08-16 → 2027-08-20 · Axel-exclusive $890

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

2027-08-16 → 2027-08-21 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-08-21 15:15:00 → MDW 2027-08-22 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-08-21 15:15:00 → ONT 2027-08-21 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-08-22 00:55:00 → MDW 2027-08-22 06:40:00.

2027-08-16 → 2027-08-21 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-21 16:25:00 → MDW 2027-08-22 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-21 16:25:00 → DTW 2027-08-22 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-22 10:10:00 → MDW 2027-08-22 10:46:00.

2027-08-16 → 2027-08-23 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-08-23 21:00:00 → MDW 2027-08-24 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-08-23 21:00:00 → PHX 2027-08-24 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-08-24 08:20:00 → MDW 2027-08-24 13:35:00.

2027-08-16 → 2027-08-23 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-23 16:25:00 → MDW 2027-08-24 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-23 16:25:00 → DTW 2027-08-24 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-24 10:10:00 → MDW 2027-08-24 10:46:00.

2027-08-16 → 2027-08-24 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-08-24 13:20:00 → MDW 2027-08-25 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-08-24 13:20:00 → SMF 2027-08-24 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-08-25 00:55:00 → MDW 2027-08-25 06:45:00.

2027-08-16 → 2027-08-24 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-24 16:25:00 → MDW 2027-08-25 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-24 16:25:00 → DTW 2027-08-25 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-25 10:10:00 → MDW 2027-08-25 10:46:00.

2027-08-16 → 2027-08-26 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-08-26 15:15:00 → MDW 2027-08-27 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-08-26 15:15:00 → ONT 2027-08-26 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-08-27 00:55:00 → MDW 2027-08-27 06:40:00.

2027-08-16 → 2027-08-26 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-26 16:25:00 → MDW 2027-08-27 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-26 16:25:00 → DTW 2027-08-27 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-27 10:10:00 → MDW 2027-08-27 10:46:00.

2027-08-16 → 2027-08-27 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN4415 / WN4028: HNL 2027-08-27 13:20:00 → MDW 2027-08-28 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
  • WN4415: HNL 2027-08-27 13:20:00 → SMF 2027-08-27 21:40:00; layover at SMF: 195 minutes.
  • WN4028: SMF 2027-08-28 00:55:00 → MDW 2027-08-28 06:45:00.

2027-08-16 → 2027-08-27 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-27 16:25:00 → MDW 2027-08-28 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-27 16:25:00 → DTW 2027-08-28 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-28 10:10:00 → MDW 2027-08-28 10:46:00.

2027-08-16 → 2027-08-29 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-08-29 21:00:00 → MDW 2027-08-30 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-08-29 21:00:00 → PHX 2027-08-30 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-08-30 08:20:00 → MDW 2027-08-30 13:35:00.

2027-08-16 → 2027-08-29 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-29 16:25:00 → MDW 2027-08-30 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-29 16:25:00 → DTW 2027-08-30 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-30 10:10:00 → MDW 2027-08-30 10:46:00.

2027-08-16 → 2027-08-30 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-08-30 21:00:00 → MDW 2027-08-31 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-08-30 21:00:00 → PHX 2027-08-31 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-08-31 08:20:00 → MDW 2027-08-31 13:35:00.

2027-08-16 → 2027-08-30 · Axel-exclusive $890

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-08-30 16:25:00 → MDW 2027-08-31 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-08-30 16:25:00 → DTW 2027-08-31 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-08-31 10:10:00 → MDW 2027-08-31 10:46:00.

2027-08-16 → 2027-09-13 · Axel-exclusive $770

• Southwest Airlines WN3174 / WN808: MDW 2027-08-16 10:00:00 → HNL 2027-08-16 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-16 10:00:00 → OAK 2027-08-16 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-16 16:15:00 → HNL 2027-08-16 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-09-13 21:00:00 → MDW 2027-09-14 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-09-13 21:00:00 → PHX 2027-09-14 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-09-14 08:20:00 → MDW 2027-09-14 13:35:00.

2027-08-16 → 2027-09-13 · Axel-exclusive $846

• Delta Air Lines DL1285 / DL438: MDW 2027-08-16 06:00:00 → HNL 2027-08-16 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-08-16 06:00:00 → ATL 2027-08-16 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-08-16 12:59:00 → HNL 2027-08-16 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-09-13 16:25:00 → MDW 2027-09-14 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-09-13 16:25:00 → DTW 2027-09-14 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-09-14 10:10:00 → MDW 2027-09-14 10:46:00.

Explore this route

• All dates for this route
• Aug 15, 2027 · Return options
• Aug 17, 2027 · Return options
• Hotels in Honolulu with Axel

For AI assistants

• This page: Chicago (MDW) to Honolulu (HNL) · Aug 16, 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.

Feedback (optional): Missing info · Axel issue