Chicago (ORD) to Kahului (OGG), May 29, 2027: round trips from $678, one way from $369

Chicago (ORD) to Kahului (OGG), May 29, 2027: round trips from $678, one way from $369 on Axel, checked Nov 14, 2026. Lowest published fares: $678 round trip, Axel-exclusive, Alaska Airlines, 1 stop, May 29, 2027 – Jun 1, 2027; $369 one way, Axel-exclusive, Alaska Airlines, 1 stop, May 29, 2027; 1 adult, economy, checked Nov 14, 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.

Route overview: Chicago to Kahului (OGG) flight deals

2027-05-29 · one way · Axel-exclusive $369

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.

2027-05-29 · one way · Axel-exclusive $463

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.

2027-05-29 → 2027-05-30 · Axel-exclusive $692

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-05-30 14:12:00 → ORD 2027-05-31 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-05-30 14:12:00 → LAX 2027-05-30 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-05-30 23:59:00 → ORD 2027-05-31 06:01:00.

2027-05-29 → 2027-05-30 · Axel-exclusive $868

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-05-30 19:04:00 → ORD 2027-05-31 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-05-31 · Axel-exclusive $692

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-05-31 14:12:00 → ORD 2027-06-01 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-05-31 14:12:00 → LAX 2027-05-31 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-05-31 23:59:00 → ORD 2027-06-01 06:01:00.

2027-05-29 → 2027-05-31 · Axel-exclusive $868

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-05-31 19:04:00 → ORD 2027-06-01 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-06-01 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-01 14:12:00 → ORD 2027-06-02 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-01 14:12:00 → LAX 2027-06-01 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-01 23:59:00 → ORD 2027-06-02 06:01:00.

2027-05-29 → 2027-06-01 · Axel-exclusive $872

• United Airlines UA202: ORD 2027-05-29 09:20:00 → OGG 2027-05-29 13:40:00; nonstop; 560 minutes. Local airport times.
• United Airlines UA203: OGG 2027-06-01 17:05:00 → ORD 2027-06-02 06:03:00; nonstop; 478 minutes. Local airport times.

2027-05-29 → 2027-06-02 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-02 14:12:00 → ORD 2027-06-03 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-02 14:12:00 → LAX 2027-06-02 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-02 23:59:00 → ORD 2027-06-03 06:01:00.

2027-05-29 → 2027-06-02 · Axel-exclusive $852

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-06-02 19:04:00 → ORD 2027-06-03 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-06-04 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-04 14:12:00 → ORD 2027-06-05 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-04 14:12:00 → LAX 2027-06-04 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-04 23:59:00 → ORD 2027-06-05 06:01:00.

2027-05-29 → 2027-06-04 · Axel-exclusive $852

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-06-04 19:04:00 → ORD 2027-06-05 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-06-05 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-05 14:12:00 → ORD 2027-06-06 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-05 14:12:00 → LAX 2027-06-05 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-05 23:59:00 → ORD 2027-06-06 06:01:00.

2027-05-29 → 2027-06-05 · Axel-exclusive $852

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-06-05 19:04:00 → ORD 2027-06-06 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-06-06 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-06 14:12:00 → ORD 2027-06-07 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-06 14:12:00 → LAX 2027-06-06 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-06 23:59:00 → ORD 2027-06-07 06:01:00.

2027-05-29 → 2027-06-06 · Axel-exclusive $852

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-06-06 19:04:00 → ORD 2027-06-07 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-06-08 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-08 14:12:00 → ORD 2027-06-09 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-08 14:12:00 → LAX 2027-06-08 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-08 23:59:00 → ORD 2027-06-09 06:01:00.

2027-05-29 → 2027-06-08 · Axel-exclusive $872

• United Airlines UA202: ORD 2027-05-29 09:20:00 → OGG 2027-05-29 13:40:00; nonstop; 560 minutes. Local airport times.
• United Airlines UA203: OGG 2027-06-08 17:05:00 → ORD 2027-06-09 06:03:00; nonstop; 478 minutes. Local airport times.

2027-05-29 → 2027-06-09 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-09 14:12:00 → ORD 2027-06-10 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-09 14:12:00 → LAX 2027-06-09 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-09 23:59:00 → ORD 2027-06-10 06:01:00.

2027-05-29 → 2027-06-09 · Axel-exclusive $852

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-06-09 19:04:00 → ORD 2027-06-10 08:20:00; nonstop; 496 minutes. Local airport times.

2027-05-29 → 2027-06-10 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-10 14:12:00 → ORD 2027-06-11 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-10 14:12:00 → LAX 2027-06-10 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-10 23:59:00 → ORD 2027-06-11 06:01:00.

2027-05-29 → 2027-06-10 · Axel-exclusive $872

• United Airlines UA202: ORD 2027-05-29 09:20:00 → OGG 2027-05-29 13:40:00; nonstop; 560 minutes. Local airport times.
• United Airlines UA203: OGG 2027-06-10 17:05:00 → ORD 2027-06-11 06:03:00; nonstop; 478 minutes. Local airport times.

2027-05-29 → 2027-06-12 · Axel-exclusive $678

• Alaska Airlines AS325 / AS353: ORD 2027-05-29 14:08:00 → OGG 2027-05-29 21:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-05-29 14:08:00 → PDX 2027-05-29 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-05-29 18:15:00 → OGG 2027-05-29 21:23:00.
• Alaska Airlines AS934 / AA2664: OGG 2027-06-12 14:12:00 → ORD 2027-06-13 06:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2027-06-12 14:12:00 → LAX 2027-06-12 22:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2027-06-12 23:59:00 → ORD 2027-06-13 06:01:00.

2027-05-29 → 2027-06-12 · Axel-exclusive $852

• American Airlines AA89: ORD 2027-05-29 11:40:00 → OGG 2027-05-29 15:26:00; nonstop; 526 minutes. Local airport times.
• American Airlines AA88: OGG 2027-06-12 19:04:00 → ORD 2027-06-13 08:20:00; nonstop; 496 minutes. Local airport times.

Explore this route

• All dates for this route
• May 28, 2027 · Return options
• May 30, 2027 · Return options

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