Chicago (MDW) to Honolulu (HNL)

Lowest published fares for the months ahead: $670 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Dec 3–6, 2026; $350 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 1, 2026; 144 priced flights on 72 exact dates, 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.

Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.

Chicago (MDW) to Honolulu (HNL): November 2026

Chicago (MDW) to Honolulu (HNL): December 2026

Chicago (MDW) to Honolulu (HNL): January 2027

Chicago (MDW) to Honolulu (HNL): February 2027

Chicago (MDW) to Honolulu (HNL): March 2027

Chicago (MDW) to Honolulu (HNL): April 2027

Chicago (MDW) to Honolulu (HNL): May 2027

Chicago (MDW) to Honolulu (HNL): June 2027

Chicago (MDW) to Honolulu (HNL): July 2027

Chicago (MDW) to Honolulu (HNL): August 2027

Chicago (MDW) to Honolulu (HNL): September 2027

Chicago (MDW) to Honolulu (HNL): October 2027

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 (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $115 a night, $575 for 5 nights · 4★ Hotel La Croix, $157 a night, $783 for 5 nights · 5★ Renaissance Honolulu Hotel & Spa, $290 a night, $1,452 for 5 nights
• Hotels in Honolulu for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $123 a night, $369 for 3 nights · 4★ Hotel La Croix, $162 a night, $487 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $294 a night, $881 for 3 nights
• Hotels in Honolulu for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $123 a night, $369 for 3 nights · 4★ Hotel La Croix, $162 a night, $487 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $286 a night, $859 for 3 nights
• Hotels in Honolulu for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $113 a night, $791 for 7 nights · 4★ Hotel La Croix, $159 a night, $1,113 for 7 nights · 5★ Renaissance Honolulu Hotel & Spa, $290 a night, $2,033 for 7 nights
• Hotels in Honolulu for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $120 a night, $361 for 3 nights · 4★ Hotel La Croix, $166 a night, $497 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $293 a night, $879 for 3 nights
• Hotels in Honolulu for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $120 a night, $361 for 3 nights · 4★ Hotel La Croix, $165 a night, $495 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $290 a night, $870 for 3 nights
• Hotels in Honolulu for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $139 a night, $970 for 7 nights · 4★ Hotel La Croix, $181 a night, $1,265 for 7 nights · 5★ Renaissance Honolulu Hotel & Spa, $303 a night, $2,119 for 7 nights
• Hotels in Honolulu for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ The Equus, $201 a night, $602 for 3 nights · 4★ Queen Kapiolani Hotel, $213 a night, $640 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $370 a night, $1,110 for 3 nights
• Hotels in Honolulu for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ The Equus, $204 a night, $612 for 3 nights · 4★ Sheraton Princess Kaiulani Waikiki Beach, $227 a night, $680 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $384 a night, $1,153 for 3 nights
• Hotels in Honolulu for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ The Equus, $163 a night, $1,142 for 7 nights · 4★ Hotel La Croix, $198 a night, $1,387 for 7 nights · 5★ Renaissance Honolulu Hotel & Spa, $341 a night, $2,386 for 7 nights
• Hotels in Honolulu for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $133 a night, $398 for 3 nights · 4★ Hotel La Croix, $172 a night, $515 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $294 a night, $881 for 3 nights
• Hotels in Honolulu for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $137 a night, $412 for 3 nights · 4★ Hotel La Croix, $177 a night, $531 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $293 a night, $880 for 3 nights
• Hotels in Honolulu for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $151 a night, $1,057 for 7 nights · 4★ Hotel La Croix, $215 a night, $1,505 for 7 nights · 5★ Renaissance Honolulu Hotel & Spa, $407 a night, $2,848 for 7 nights
• Hotels in Honolulu for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $173 a night, $866 for 5 nights · 4★ Hotel La Croix, $251 a night, $1,257 for 5 nights · 5★ Alohilani Resort Waikiki Beach, $457 a night, $2,287 for 5 nights
• Hotels in Honolulu for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $198 a night, $593 for 3 nights · 4★ Hotel La Croix, $298 a night, $894 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $489 a night, $1,466 for 3 nights
• Hotels in Honolulu for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $199 a night, $596 for 3 nights · 4★ Hotel La Croix, $295 a night, $886 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $483 a night, $1,450 for 3 nights
• Hotels in Honolulu for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $210 a night, $1,471 for 7 nights · 4★ Hotel La Croix, $285 a night, $1,996 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $487 a night, $3,406 for 7 nights
• Hotels in Honolulu for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $212 a night, $635 for 3 nights · 4★ Aston Waikiki Sunset, $255 a night, $763.50 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $492 a night, $1,475 for 3 nights
• Hotels in Honolulu for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $214 a night, $643 for 3 nights · 4★ Aston Waikiki Sunset, $245 a night, $733.50 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $427 a night, $1,281 for 3 nights
• Hotels in Honolulu for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $179 a night, $536 for 3 nights · 4★ Aston Waikiki Sunset, $226 a night, $678 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $299 a night, $897 for 3 nights
• Hotels in Honolulu for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $149 a night, $1,041 for 7 nights · 4★ Hotel La Croix, $188 a night, $1,313 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $268 a night, $1,873 for 7 nights
• Hotels in Honolulu for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $136 a night, $408 for 3 nights · 4★ Hotel La Croix, $170 a night, $509 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $270 a night, $810 for 3 nights
• Hotels in Honolulu for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $129 a night, $387 for 3 nights · 4★ Hotel La Croix, $183 a night, $549 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $265 a night, $795 for 3 nights
• Hotels in Honolulu for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $133 a night, $928 for 7 nights · 4★ Hotel La Croix, $196 a night, $1,371 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $263 a night, $1,840 for 7 nights
• Hotels in Honolulu for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $144 a night, $432 for 3 nights · 4★ Aston Waikiki Sunset, $202 a night, $606 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $281 a night, $843 for 3 nights
• Hotels in Honolulu for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $146 a night, $437 for 3 nights · 4★ Aston Waikiki Sunset, $205 a night, $614 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $275 a night, $824 for 3 nights
• Hotels in Honolulu for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $138 a night, $967 for 7 nights · 4★ Aston Waikiki Sunset, $204 a night, $1,427 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $268 a night, $1,876 for 7 nights
• Hotels in Honolulu for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $141 a night, $422 for 3 nights · 4★ Aston Waikiki Sunset, $196 a night, $589 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $265 a night, $795 for 3 nights
• Hotels in Honolulu for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $137 a night, $412 for 3 nights · 4★ Hotel La Croix, $184 a night, $553 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $266 a night, $798 for 3 nights
• Hotels in Honolulu for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $134 a night, $937 for 7 nights · 4★ Hotel La Croix, $177 a night, $1,237 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $259 a night, $1,813 for 7 nights
• Hotels in Honolulu for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $139 a night, $416 for 3 nights · 4★ Hotel La Croix, $183 a night, $548 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $266 a night, $798 for 3 nights
• Hotels in Honolulu for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $139 a night, $417 for 3 nights · 4★ Hotel La Croix, $177 a night, $532 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $260 a night, $781 for 3 nights
• Hotels in Honolulu for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $133 a night, $928 for 7 nights · 4★ Hotel La Croix, $174 a night, $1,217 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $248 a night, $1,736 for 7 nights
• Hotels in Honolulu for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $138 a night, $413 for 3 nights · 4★ Hotel La Croix, $174 a night, $521 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $258 a night, $775 for 3 nights
• Hotels in Honolulu for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $137 a night, $410 for 3 nights · 4★ Hotel La Croix, $177 a night, $532 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $260 a night, $779 for 3 nights
• Hotels in Honolulu for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $134 a night, $937 for 7 nights · 4★ Hotel La Croix, $187 a night, $1,309 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $267 a night, $1,868 for 7 nights
• Hotels in Honolulu for these nights (Feb 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $138 a night, $413 for 3 nights · 4★ Aston Waikiki Sunset, $199 a night, $596 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $296 a night, $889 for 3 nights
• Hotels in Honolulu for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $138 a night, $413 for 3 nights · 4★ Hotel La Croix, $194 a night, $581 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $292 a night, $877 for 3 nights
• Hotels in Honolulu for these nights (Feb 13–20, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $134 a night, $937 for 7 nights · 4★ Hotel La Croix, $190 a night, $1,332 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $283 a night, $1,978 for 7 nights
• Hotels in Honolulu for these nights (Feb 26 – Mar 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $136 a night, $409 for 3 nights · 4★ Hotel La Croix, $179 a night, $536 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $270 a night, $810 for 3 nights
• Hotels in Honolulu for these nights (Feb 27 – Mar 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $128 a night, $899 for 7 nights · 4★ Hotel La Croix, $173 a night, $1,214 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $261 a night, $1,830 for 7 nights
• Hotels in Honolulu for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $124 a night, $497 for 4 nights · 4★ Hotel La Croix, $185 a night, $740 for 4 nights · 5★ Renaissance Honolulu Hotel & Spa, $275 a night, $1,100 for 4 nights
• Hotels in Honolulu for these nights (Mar 26–29, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $125 a night, $375 for 3 nights · 4★ Hotel La Croix, $185 a night, $554 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $275 a night, $825 for 3 nights
• Hotels in Honolulu for these nights (Mar 27 – Apr 3, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $127 a night, $887 for 7 nights · 4★ Hotel La Croix, $176 a night, $1,231 for 7 nights · 5★ Renaissance Honolulu Hotel & Spa, $272 a night, $1,901 for 7 nights
• Hotels in Honolulu for these nights (Apr 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $135 a night, $406 for 3 nights · 4★ Aston Waikiki Sunset, $196 a night, $587 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $258 a night, $774 for 3 nights
• Hotels in Honolulu for these nights (Apr 24 – May 1, 2027 · 7 nights · 2 adults, 1 room): 3★ Ramada Plaza by Wyndham Waikiki, $128 a night, $898 for 7 nights · 4★ Hotel La Croix, $186 a night, $1,301 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $257 a night, $1,801 for 7 nights
• Hotels in Honolulu for these nights (May 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $158 a night, $475 for 3 nights · 4★ Hotel La Croix, $185 a night, $554 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $274 a night, $822 for 3 nights
• Hotels in Honolulu for these nights (May 22–29, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $150 a night, $1,053 for 7 nights · 4★ Hotel La Croix, $182 a night, $1,275 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $271 a night, $1,894 for 7 nights
• Hotels in Honolulu for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $137 a night, $410 for 3 nights · 4★ Hotel La Croix, $185 a night, $554 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $276 a night, $828 for 3 nights
• Hotels in Honolulu for these nights (Jun 18–21, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $151 a night, $454 for 3 nights · 4★ Hotel La Croix, $223 a night, $670 for 3 nights · 5★ Renaissance Honolulu Hotel & Spa, $287 a night, $862 for 3 nights
• Hotels in Honolulu for these nights (Jun 19–26, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $150 a night, $1,052 for 7 nights · 4★ Aston Waikiki Sunset, $217 a night, $1,520 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $281 a night, $1,966 for 7 nights
• Hotels in Honolulu for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ The Equus, $154 a night, $616 for 4 nights · 4★ Sheraton Princess Kaiulani Waikiki Beach, $224 a night, $896 for 4 nights · 5★ Renaissance Honolulu Hotel & Spa, $300 a night, $1,200 for 4 nights
• Hotels in Honolulu for these nights (Jul 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ The Equus, $147 a night, $440 for 3 nights · 4★ Aston Waikiki Sunset, $226 a night, $678 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $296 a night, $887 for 3 nights
• Hotels in Honolulu for these nights (Jul 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $162 a night, $1,132 for 7 nights · 4★ Hotel La Croix, $223 a night, $1,561 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $292 a night, $2,043 for 7 nights
• Hotels in Honolulu for these nights (Aug 13–16, 2027 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $175 a night, $526 for 3 nights · 4★ Hotel La Croix, $202 a night, $605 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $284 a night, $853 for 3 nights
• Hotels in Honolulu for these nights (Aug 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $164 a night, $1,150 for 7 nights · 4★ Hotel La Croix, $205 a night, $1,436 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $264 a night, $1,847 for 7 nights
• Hotels in Honolulu for these nights (Sep 3–6, 2027 · 3 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 (Sep 10–13, 2027 · 3 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 (Sep 11–18, 2027 · 7 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 (Oct 1–4, 2027 · 3 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 (Oct 2–9, 2027 · 7 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

2026-11-24 → 2026-11-29 · Axel-exclusive $804

• Southwest Airlines WN3020 / WN2881: MDW 2026-11-24 06:00:00 → HNL 2026-11-24 14:00:00; 1 stop(s) via SAN; 720 minutes. Local airport times.
  • WN3020: MDW 2026-11-24 06:00:00 → SAN 2026-11-24 08:30:00; layover at SAN: 85 minutes.
  • WN2881: SAN 2026-11-24 09:55:00 → HNL 2026-11-24 14:00:00.
• Southwest Airlines WN1276 / WN3443: HNL 2026-11-29 21:00:00 → MDW 2026-11-30 12:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2026-11-29 21:00:00 → PHX 2026-11-30 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2026-11-30 08:20:00 → MDW 2026-11-30 12:35:00.

2026-11-24 → 2026-11-29 · Axel-exclusive $888

• Delta Air Lines DL1285 / DL438: MDW 2026-11-24 06:00:00 → HNL 2026-11-24 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2026-11-24 06:00:00 → ATL 2026-11-24 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2026-11-24 12:59:00 → HNL 2026-11-24 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2026-11-29 16:25:00 → MDW 2026-11-30 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2026-11-29 16:25:00 → DTW 2026-11-30 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2026-11-30 09:10:00 → MDW 2026-11-30 09:46:00.

2026-12-01 · one way · Axel-exclusive $350

• Southwest Airlines WN3020 / WN2881: MDW 2026-12-01 06:00:00 → HNL 2026-12-01 14:00:00; 1 stop(s) via SAN; 720 minutes. Local airport times.
  • WN3020: MDW 2026-12-01 06:00:00 → SAN 2026-12-01 08:30:00; layover at SAN: 85 minutes.
  • WN2881: SAN 2026-12-01 09:55:00 → HNL 2026-12-01 14:00:00.

2026-12-01 · one way · Axel-exclusive $390

• Delta Air Lines DL1285 / DL438: MDW 2026-12-01 06:00:00 → HNL 2026-12-01 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2026-12-01 06:00:00 → ATL 2026-12-01 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2026-12-01 12:59:00 → HNL 2026-12-01 18:02:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $670

• Southwest Airlines WN2995 / WN4524: MDW 2026-12-05 05:05:00 → HNL 2026-12-05 14:00:00; 1 stop(s) via PHX; 775 minutes. Local airport times.
  • WN2995: MDW 2026-12-05 05:05:00 → PHX 2026-12-05 07:55:00; layover at PHX: 145 minutes.
  • WN4524: PHX 2026-12-05 10:20:00 → HNL 2026-12-05 14:00:00.
• Southwest Airlines WN1276 / WN3443: HNL 2026-12-12 21:00:00 → MDW 2026-12-13 12:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2026-12-12 21:00:00 → PHX 2026-12-13 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2026-12-13 08:20:00 → MDW 2026-12-13 12:35:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $740

• Delta Air Lines DL1285 / DL438: MDW 2026-12-05 06:00:00 → HNL 2026-12-05 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2026-12-05 06:00:00 → ATL 2026-12-05 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2026-12-05 12:59:00 → HNL 2026-12-05 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2026-12-12 16:25:00 → MDW 2026-12-13 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2026-12-12 16:25:00 → DTW 2026-12-13 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2026-12-13 09:10:00 → MDW 2026-12-13 09:46:00.

2026-12-19 → 2026-12-26 · Axel-exclusive $972

• Southwest Airlines WN2995 / WN4524: MDW 2026-12-19 05:05:00 → HNL 2026-12-19 14:00:00; 1 stop(s) via PHX; 775 minutes. Local airport times.
  • WN2995: MDW 2026-12-19 05:05:00 → PHX 2026-12-19 07:55:00; layover at PHX: 145 minutes.
  • WN4524: PHX 2026-12-19 10:20:00 → HNL 2026-12-19 14:00:00.
• Southwest Airlines WN2038 / WN3310: HNL 2026-12-26 15:15:00 → MDW 2026-12-27 05:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2026-12-26 15:15:00 → ONT 2026-12-26 22:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2026-12-26 23:55:00 → MDW 2026-12-27 05:40:00.

2026-12-19 → 2026-12-26 · Axel-exclusive $1,073

• Delta Air Lines DL1285 / DL438: MDW 2026-12-19 06:00:00 → HNL 2026-12-19 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2026-12-19 06:00:00 → ATL 2026-12-19 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2026-12-19 12:59:00 → HNL 2026-12-19 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2026-12-26 16:25:00 → MDW 2026-12-27 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2026-12-26 16:25:00 → DTW 2026-12-27 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2026-12-27 09:10:00 → MDW 2026-12-27 09:46:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $972

• Southwest Airlines WN3174 / WN808: MDW 2026-12-31 10:00:00 → HNL 2026-12-31 19:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2026-12-31 10:00:00 → OAK 2026-12-31 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2026-12-31 16:15:00 → HNL 2026-12-31 19:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-01-03 21:00:00 → MDW 2027-01-04 12:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-01-03 21:00:00 → PHX 2027-01-04 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-01-04 08:20:00 → MDW 2027-01-04 12:35:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $1,073

• Delta Air Lines DL1285 / DL438: MDW 2026-12-31 06:00:00 → HNL 2026-12-31 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2026-12-31 06:00:00 → ATL 2026-12-31 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2026-12-31 12:59:00 → HNL 2026-12-31 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-01-03 16:25:00 → MDW 2027-01-04 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-01-03 16:25:00 → DTW 2027-01-04 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-01-04 09:10:00 → MDW 2027-01-04 09:46:00.

2027-01-14 → 2027-01-17 · Axel-exclusive $704

• Southwest Airlines WN3174 / WN808: MDW 2027-01-14 10:00:00 → HNL 2027-01-14 19:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-01-14 10:00:00 → OAK 2027-01-14 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-01-14 16:15:00 → HNL 2027-01-14 19:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-01-17 21:00:00 → MDW 2027-01-18 12:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-01-17 21:00:00 → PHX 2027-01-18 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-01-18 08:20:00 → MDW 2027-01-18 12:35:00.

2027-01-14 → 2027-01-17 · Axel-exclusive $777

• Delta Air Lines DL1285 / DL438: MDW 2027-01-14 06:00:00 → HNL 2027-01-14 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-01-14 06:00:00 → ATL 2027-01-14 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-01-14 12:59:00 → HNL 2027-01-14 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-01-17 16:25:00 → MDW 2027-01-18 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-01-17 16:25:00 → DTW 2027-01-18 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-01-18 09:10:00 → MDW 2027-01-18 09:46:00.

2027-01-28 → 2027-01-31 · Axel-exclusive $670

• Southwest Airlines WN3174 / WN808: MDW 2027-01-28 10:00:00 → HNL 2027-01-28 19:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-01-28 10:00:00 → OAK 2027-01-28 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-01-28 16:15:00 → HNL 2027-01-28 19:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-01-31 21:00:00 → MDW 2027-02-01 12:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-01-31 21:00:00 → PHX 2027-02-01 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-02-01 08:20:00 → MDW 2027-02-01 12:35:00.

2027-01-28 → 2027-01-31 · Axel-exclusive $740

• Delta Air Lines DL1285 / DL438: MDW 2027-01-28 06:00:00 → HNL 2027-01-28 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-01-28 06:00:00 → ATL 2027-01-28 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-01-28 12:59:00 → HNL 2027-01-28 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-01-31 16:25:00 → MDW 2027-02-01 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-01-31 16:25:00 → DTW 2027-02-01 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-02-01 09:10:00 → MDW 2027-02-01 09:46:00.

2027-02-11 → 2027-02-14 · Axel-exclusive $720

• Southwest Airlines WN3174 / WN808: MDW 2027-02-11 10:00:00 → HNL 2027-02-11 19:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-02-11 10:00:00 → OAK 2027-02-11 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-02-11 16:15:00 → HNL 2027-02-11 19:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-02-14 21:00:00 → MDW 2027-02-15 12:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-02-14 21:00:00 → PHX 2027-02-15 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-02-15 08:20:00 → MDW 2027-02-15 12:35:00.

2027-02-11 → 2027-02-14 · Axel-exclusive $796

• Delta Air Lines DL1285 / DL438: MDW 2027-02-11 06:00:00 → HNL 2027-02-11 18:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-02-11 06:00:00 → ATL 2027-02-11 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-02-11 12:59:00 → HNL 2027-02-11 18:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-02-14 16:25:00 → MDW 2027-02-15 09:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-02-14 16:25:00 → DTW 2027-02-15 06:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-02-15 09:10:00 → MDW 2027-02-15 09:46:00.

2027-03-26 → 2027-03-29 · Axel-exclusive $888

• Southwest Airlines WN3174 / WN808: MDW 2027-03-26 10:00:00 → HNL 2027-03-26 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-03-26 10:00:00 → OAK 2027-03-26 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-03-26 16:15:00 → HNL 2027-03-26 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-03-29 21:00:00 → MDW 2027-03-30 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-03-29 21:00:00 → PHX 2027-03-30 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-03-30 08:20:00 → MDW 2027-03-30 13:35:00.

2027-03-26 → 2027-03-29 · Axel-exclusive $978

• Delta Air Lines DL1285 / DL438: MDW 2027-03-26 06:00:00 → HNL 2027-03-26 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-03-26 06:00:00 → ATL 2027-03-26 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-03-26 12:59:00 → HNL 2027-03-26 17:02:00.
• Delta Air Lines DL386 / DL4684: HNL 2027-03-29 16:25:00 → MDW 2027-03-30 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
  • DL386: HNL 2027-03-29 16:25:00 → DTW 2027-03-30 07:00:00; layover at DTW: 190 minutes.
  • DL4684: DTW 2027-03-30 10:10:00 → MDW 2027-03-30 10:46:00.

2027-05-28 → 2027-05-31 · Axel-exclusive $842

• Southwest Airlines WN3174 / WN808: MDW 2027-05-28 10:00:00 → HNL 2027-05-28 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-05-28 10:00:00 → OAK 2027-05-28 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-05-28 16:15:00 → HNL 2027-05-28 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.

2027-05-28 → 2027-05-31 · Axel-exclusive $926

• Delta Air Lines DL1285 / DL438: MDW 2027-05-28 06:00:00 → HNL 2027-05-28 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
  • DL1285: MDW 2027-05-28 06:00:00 → ATL 2027-05-28 09:03:00; layover at ATL: 236 minutes.
  • DL438: ATL 2027-05-28 12:59:00 → HNL 2027-05-28 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.

2027-08-13 → 2027-08-16 · Axel-exclusive $810

• Southwest Airlines WN3174 / WN808: MDW 2027-08-13 10:00:00 → HNL 2027-08-13 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
  • WN3174: MDW 2027-08-13 10:00:00 → OAK 2027-08-13 12:40:00; layover at OAK: 215 minutes.
  • WN808: OAK 2027-08-13 16:15:00 → HNL 2027-08-13 18:45:00.
• Southwest Airlines WN1276 / WN3443: HNL 2027-08-16 21:00:00 → MDW 2027-08-17 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
  • WN1276: HNL 2027-08-16 21:00:00 → PHX 2027-08-17 06:00:00; layover at PHX: 140 minutes.
  • WN3443: PHX 2027-08-17 08:20:00 → MDW 2027-08-17 13:35:00.

2027-08-13 → 2027-08-16 · Axel-exclusive $890

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

2027-10-02 → 2027-10-09 · Axel-exclusive $770

• Southwest Airlines WN2995 / WN4524: MDW 2027-10-02 05:05:00 → HNL 2027-10-02 13:00:00; 1 stop(s) via PHX; 775 minutes. Local airport times.
  • WN2995: MDW 2027-10-02 05:05:00 → PHX 2027-10-02 06:55:00; layover at PHX: 145 minutes.
  • WN4524: PHX 2027-10-02 09:20:00 → HNL 2027-10-02 13:00:00.
• Southwest Airlines WN2038 / WN3310: HNL 2027-10-09 15:15:00 → MDW 2027-10-10 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
  • WN2038: HNL 2027-10-09 15:15:00 → ONT 2027-10-09 23:45:00; layover at ONT: 70 minutes.
  • WN3310: ONT 2027-10-10 00:55:00 → MDW 2027-10-10 06:40:00.

2027-10-02 → 2027-10-09 · Axel-exclusive $846

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

More dates for this route

• Nov 24, 2026 · Return options
• Dec 4, 2026 · Return options
• Dec 15, 2026 · Return options
• Dec 25, 2026 · Return options
• Jan 2, 2027 · Return options
• Jan 15, 2027 · Return options
• Jan 26, 2027 · Return options
• Feb 6, 2027 · Return options
• Feb 27, 2027 · Return options
• May 22, 2027 · Return options
• Jul 17, 2027 · Return options
• Oct 2, 2027 · Return options
• Hotels in Honolulu with Axel

For AI assistants

• This page: Chicago (MDW) to Honolulu (HNL): 144 priced flights on 72 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check. 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: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
• 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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