Flights from Maui to the Midwest for 3 days

Flights for your trip

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

2026-11-20 · one way · $385.00

• American Airlines AA88: OGG 2026-11-20 19:04:00 → ORD 2026-11-21 07:20:00; nonstop; 496 minutes. Local airport times.

2026-11-20 · one way · $395.00

• United Airlines UA203: OGG 2026-11-20 17:05:00 → ORD 2026-11-21 05:03:00; nonstop; 478 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $841.50

• United Airlines UA203: OGG 2026-11-20 17:05:00 → ORD 2026-11-21 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2026-11-23 09:20:00 → OGG 2026-11-23 14:40:00; nonstop; 560 minutes. Local airport times.

2026-11-20 · one way · $325.00

• Alaska Airlines AS558 / AS324: OGG 2026-11-20 22:23:00 → ORD 2026-11-21 13:10:00; 1 stop(s) via PDX; 647 minutes. Local airport times.
  • AS558: OGG 2026-11-20 22:23:00 → PDX 2026-11-21 05:49:00; layover at PDX: 71 minutes.
  • AS324: PDX 2026-11-21 07:00:00 → ORD 2026-11-21 13:10:00.

2026-11-20 · one way · $355.00

• Delta Air Lines DL805 / DL1810: OGG 2026-11-20 17:59:00 → ORD 2026-11-21 09:04:00; 1 stop(s) via MSP; 665 minutes. Local airport times.
  • DL805: OGG 2026-11-20 17:59:00 → MSP 2026-11-21 05:30:00; layover at MSP: 105 minutes.
  • DL1810: MSP 2026-11-21 07:15:00 → ORD 2026-11-21 09:04:00.

2026-11-27 → 2026-12-04 · $693.00

• Alaska Airlines AS934 / AA2664: OGG 2026-11-27 14:12:00 → ORD 2026-11-28 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-11-27 14:12:00 → LAX 2026-11-27 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-11-27 22:59:00 → ORD 2026-11-28 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2026-12-04 14:08:00 → OGG 2026-12-04 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2026-12-04 14:08:00 → PDX 2026-12-04 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2026-12-04 18:15:00 → OGG 2026-12-04 22:23:00.

2026-11-27 → 2026-12-04 · $715.00

• American Airlines AA426 / AA1149: OGG 2026-11-27 22:50:00 → ORD 2026-11-28 13:52:00; 1 stop(s) via PHX; 662 minutes. Local airport times.
  • AA426: OGG 2026-11-27 22:50:00 → PHX 2026-11-28 07:42:00; layover at PHX: 93 minutes.
  • AA1149: PHX 2026-11-28 09:15:00 → ORD 2026-11-28 13:52:00.
• American Airlines AA597 / AS1464: ORD 2026-12-04 13:24:00 → OGG 2026-12-04 21:19:00; 1 stop(s) via SFO; 715 minutes. Local airport times.
  • AA597: ORD 2026-12-04 13:24:00 → SFO 2026-12-04 16:27:00; layover at SFO: 63 minutes.
  • AS1464: SFO 2026-12-04 17:30:00 → OGG 2026-12-04 21:19:00.

2026-11-27 → 2026-12-04 · $753.50

• Delta Air Lines DL805 / DL1810: OGG 2026-11-27 17:59:00 → ORD 2026-11-28 09:04:00; 1 stop(s) via MSP; 665 minutes. Local airport times.
  • DL805: OGG 2026-11-27 17:59:00 → MSP 2026-11-28 05:30:00; layover at MSP: 105 minutes.
  • DL1810: MSP 2026-11-28 07:15:00 → ORD 2026-11-28 09:04:00.
• Delta Air Lines DL2231 / DL623: ORD 2026-12-04 07:30:00 → OGG 2026-12-04 15:20:00; 1 stop(s) via SLC; 710 minutes. Local airport times.
  • DL2231: ORD 2026-12-04 07:30:00 → SLC 2026-12-04 10:10:00; layover at SLC: 80 minutes.
  • DL623: SLC 2026-12-04 11:30:00 → OGG 2026-12-04 15:20:00.

2026-11-27 → 2026-12-04 · $841.50

• United Airlines UA203: OGG 2026-11-27 17:05:00 → ORD 2026-11-28 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2026-12-04 09:20:00 → OGG 2026-12-04 14:40:00; nonstop; 560 minutes. Local airport times.

2026-11-20 · one way · $325.00

• Alaska Airlines AS932 / AA3278: OGG 2026-11-20 15:37:00 → ORD 2026-11-21 05:59:00; 1 stop(s) via LAS; 622 minutes. Local airport times.
  • AS932: OGG 2026-11-20 15:37:00 → LAS 2026-11-20 23:05:00; layover at LAS: 80 minutes.
  • AA3278: LAS 2026-11-21 00:25:00 → ORD 2026-11-21 05:59:00.

2026-11-20 · one way · $325.00

• Alaska Airlines AS934 / AA2664: OGG 2026-11-20 14:12:00 → ORD 2026-11-21 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-11-20 14:12:00 → LAX 2026-11-20 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-11-20 22:59:00 → ORD 2026-11-21 05:01:00.

2026-11-20 · one way · $335.00

• American Airlines AA426 / AA1149: OGG 2026-11-20 22:50:00 → ORD 2026-11-21 13:52:00; 1 stop(s) via PHX; 662 minutes. Local airport times.
  • AA426: OGG 2026-11-20 22:50:00 → PHX 2026-11-21 07:42:00; layover at PHX: 93 minutes.
  • AA1149: PHX 2026-11-21 09:15:00 → ORD 2026-11-21 13:52:00.

2026-11-20 · one way · $355.00

• Delta Air Lines DL397 / DL2247: OGG 2026-11-20 21:00:00 → ORD 2026-11-21 12:03:00; 1 stop(s) via SLC; 663 minutes. Local airport times.
  • DL397: OGG 2026-11-20 21:00:00 → SLC 2026-11-21 06:02:00; layover at SLC: 103 minutes.
  • DL2247: SLC 2026-11-21 07:45:00 → ORD 2026-11-21 12:03:00.

2026-11-20 → 2026-11-23 · $693.00

• Alaska Airlines AS932 / AA3278: OGG 2026-11-20 15:37:00 → ORD 2026-11-21 05:59:00; 1 stop(s) via LAS; 622 minutes. Local airport times.
  • AS932: OGG 2026-11-20 15:37:00 → LAS 2026-11-20 23:05:00; layover at LAS: 80 minutes.
  • AA3278: LAS 2026-11-21 00:25:00 → ORD 2026-11-21 05:59:00.
• Alaska Airlines AS325 / AS353: ORD 2026-11-23 14:08:00 → OGG 2026-11-23 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2026-11-23 14:08:00 → PDX 2026-11-23 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2026-11-23 18:15:00 → OGG 2026-11-23 22:23:00.

2026-11-27 → 2026-12-04 · $693.00

• Alaska Airlines AS932 / AA3278: OGG 2026-11-27 15:37:00 → ORD 2026-11-28 05:59:00; 1 stop(s) via LAS; 622 minutes. Local airport times.
  • AS932: OGG 2026-11-27 15:37:00 → LAS 2026-11-27 23:05:00; layover at LAS: 80 minutes.
  • AA3278: LAS 2026-11-28 00:25:00 → ORD 2026-11-28 05:59:00.
• Alaska Airlines AS325 / AS353: ORD 2026-12-04 14:08:00 → OGG 2026-12-04 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2026-12-04 14:08:00 → PDX 2026-12-04 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2026-12-04 18:15:00 → OGG 2026-12-04 22:23:00.

2026-11-20 → 2026-11-23 · $693.00

• Alaska Airlines AS934 / AA2664: OGG 2026-11-20 14:12:00 → ORD 2026-11-21 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-11-20 14:12:00 → LAX 2026-11-20 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-11-20 22:59:00 → ORD 2026-11-21 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2026-11-23 14:08:00 → OGG 2026-11-23 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2026-11-23 14:08:00 → PDX 2026-11-23 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2026-11-23 18:15:00 → OGG 2026-11-23 22:23:00.

2026-11-20 → 2026-11-23 · $715.00

• American Airlines AA426 / AA1149: OGG 2026-11-20 22:50:00 → ORD 2026-11-21 13:52:00; 1 stop(s) via PHX; 662 minutes. Local airport times.
  • AA426: OGG 2026-11-20 22:50:00 → PHX 2026-11-21 07:42:00; layover at PHX: 93 minutes.
  • AA1149: PHX 2026-11-21 09:15:00 → ORD 2026-11-21 13:52:00.
• American Airlines AA2421 / AA123: ORD 2026-11-23 06:59:00 → OGG 2026-11-23 15:31:00; 1 stop(s) via DFW; 752 minutes. Local airport times.
  • AA2421: ORD 2026-11-23 06:59:00 → DFW 2026-11-23 09:50:00; layover at DFW: 90 minutes.
  • AA123: DFW 2026-11-23 11:20:00 → OGG 2026-11-23 15:31:00.

2026-11-20 → 2026-11-23 · $753.50

• Delta Air Lines DL805 / DL1810: OGG 2026-11-20 17:59:00 → ORD 2026-11-21 09:04:00; 1 stop(s) via MSP; 665 minutes. Local airport times.
  • DL805: OGG 2026-11-20 17:59:00 → MSP 2026-11-21 05:30:00; layover at MSP: 105 minutes.
  • DL1810: MSP 2026-11-21 07:15:00 → ORD 2026-11-21 09:04:00.
• Delta Air Lines DL2231 / DL623: ORD 2026-11-23 07:30:00 → OGG 2026-11-23 15:20:00; 1 stop(s) via SLC; 710 minutes. Local airport times.
  • DL2231: ORD 2026-11-23 07:30:00 → SLC 2026-11-23 10:10:00; layover at SLC: 80 minutes.
  • DL623: SLC 2026-11-23 11:30:00 → OGG 2026-11-23 15:20:00.

2026-11-20 → 2026-11-23 · $762.50

• American Airlines AA88: OGG 2026-11-20 19:04:00 → ORD 2026-11-21 07:20:00; nonstop; 496 minutes. Local airport times.
• American Airlines AA2421 / AA123: ORD 2026-11-23 06:59:00 → OGG 2026-11-23 15:31:00; 1 stop(s) via DFW; 752 minutes. Local airport times.
  • AA2421: ORD 2026-11-23 06:59:00 → DFW 2026-11-23 09:50:00; layover at DFW: 90 minutes.
  • AA123: DFW 2026-11-23 11:20:00 → OGG 2026-11-23 15:31:00.

2026-11-27 → 2026-12-04 · $772.00

• American Airlines AA88: OGG 2026-11-27 19:04:00 → ORD 2026-11-28 07:20:00; nonstop; 496 minutes. Local airport times.
• American Airlines AA597 / AS1464: ORD 2026-12-04 13:24:00 → OGG 2026-12-04 21:19:00; 1 stop(s) via SFO; 715 minutes. Local airport times.
  • AA597: ORD 2026-12-04 13:24:00 → SFO 2026-12-04 16:27:00; layover at SFO: 63 minutes.
  • AS1464: SFO 2026-12-04 17:30:00 → OGG 2026-12-04 21:19:00.

2026-11-20 → 2026-11-23 · $784.50

• United Airlines UA203: OGG 2026-11-20 17:10:00 → ORD 2026-11-21 05:02:00; nonstop; 472 minutes. Local airport times.
• United Airlines UA2495 / UA1736: ORD 2026-11-23 08:40:00 → OGG 2026-11-23 16:37:00; 1 stop(s) via DEN; 717 minutes. Local airport times.
  • UA2495: ORD 2026-11-23 08:40:00 → DEN 2026-11-23 10:26:00; layover at DEN: 114 minutes.
  • UA1736: DEN 2026-11-23 12:20:00 → OGG 2026-11-23 16:37:00.

2026-11-27 → 2026-12-04 · $794.00

• United Airlines UA203: OGG 2026-11-27 17:10:00 → ORD 2026-11-28 05:02:00; nonstop; 472 minutes. Local airport times.
• United Airlines UA2495 / UA1736: ORD 2026-12-04 08:40:00 → OGG 2026-12-04 16:37:00; 1 stop(s) via DEN; 717 minutes. Local airport times.
  • UA2495: ORD 2026-12-04 08:40:00 → DEN 2026-12-04 10:26:00; layover at DEN: 114 minutes.
  • UA1736: DEN 2026-12-04 12:20:00 → OGG 2026-12-04 16:37:00.

More dates for this route

• Nov 20, 2026 → Nov 23, 2026
• Nov 27, 2026 → Dec 4, 2026
• Nov 20, 2026 · One way

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The Midwest for 3 days from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

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Where to stay: Where to stay in Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room

Hotels with an Axel review in Chicago: Claridge House Chicago, Tapestry Collection by Hilton · Freehand Chicago · Warwick Allerton - Chicago · The Chicago Hotel Collection - Wrigleyville · The Chicago Hotel Collection Magnificent Mile Hotel & Suites · All 154 reviewed hotels in Chicago

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