Kahului (OGG) to Chicago (ORD), Dec 28, 2026: round trips from $740, one way from $439

Kahului (OGG) to Chicago (ORD), Dec 28, 2026: round trips from $740, one way from $439 on Axel, checked Oct 29, 2026. Lowest published fares: $740 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Dec 28, 2026 – Jan 6, 2027; $439 one way, Axel-exclusive, Alaska Airlines, 1 stop, Dec 28, 2026; 1 adult, economy, checked Oct 29, 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, issued at the time 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 issuance times already shown here.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Dec 28–30, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $168 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $164 total · 5★ Sofitel Chicago Magnificent Mile, $413 total
• Hotels in Chicago for these nights (Dec 28–31, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $275 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $266 total · 5★ Sofitel Chicago Magnificent Mile, $616 total
• Hotels in Chicago for these nights (Dec 28 – Jan 1, 2027 · 4 nights · 2 adults, 1 room): 3★ The Willows Hotel, $463 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $465 total · 5★ Sofitel Chicago Magnificent Mile, $1,066 total
• Hotels in Chicago for these nights (Dec 28 – Jan 2, 2027 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $603 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $569 total · 5★ Sofitel Chicago Magnificent Mile, $1,269 total
• Hotels in Chicago for these nights (Dec 28 – Jan 3, 2027 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $732 total · 4★ Warwick Allerton - Chicago, $691 total · 5★ Sofitel Chicago Magnificent Mile, $1,479 total
• Hotels in Chicago for these nights (Dec 28 – Jan 4, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $819 total · 4★ Warwick Allerton - Chicago, $780 total · 5★ Sofitel Chicago Magnificent Mile, $1,709 total
• Hotels in Chicago for these nights (Dec 28 – Jan 5, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $894 total · 4★ Warwick Allerton - Chicago, $868 total · 5★ Sofitel Chicago Magnificent Mile, $1,919 total
• Hotels in Chicago for these nights (Dec 28 – Jan 6, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $969 total · 4★ Warwick Allerton - Chicago, $964 total · 5★ Sofitel Chicago Magnificent Mile, $2,125 total
• Hotels in Chicago for these nights (Dec 28 – Jan 7, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,052 total · 4★ Warwick Allerton - Chicago, $1,049 total · 5★ Sofitel Chicago Magnificent Mile, $2,335 total
• Hotels in Chicago for these nights (Dec 28 – Jan 8, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,127 total · 4★ Warwick Allerton - Chicago, $1,141 total · 5★ Sofitel Chicago Magnificent Mile, $2,534 total
• Hotels in Chicago for these nights (Dec 28 – Jan 9, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,210 total · 4★ Warwick Allerton - Chicago, $1,230 total · 5★ Sofitel Chicago Magnificent Mile, $2,784 total
• Hotels in Chicago for these nights (Dec 28 – Jan 10, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,285 total · 4★ Warwick Allerton - Chicago, $1,326 total · 5★ Sofitel Chicago Magnificent Mile, $3,042 total
• Hotels in Chicago for these nights (Dec 28 – Jan 11, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,360 total · 4★ Warwick Allerton - Chicago, $1,411 total · 5★ Sofitel Chicago Magnificent Mile, $3,261 total

All hotels in Chicago

Route overview: Maui to Chicago (ORD) flight deals

2026-12-28 · one way · Axel-exclusive $438.75

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.

2026-12-28 · one way · Axel-exclusive $519.75

• American Airlines AA88: OGG 2026-12-28 19:04:00 → ORD 2026-12-29 07:20:00; nonstop; 496 minutes. Local airport times.

2026-12-28 → 2026-12-30 · Axel-exclusive $850.50

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2026-12-30 14:08:00 → OGG 2026-12-30 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2026-12-30 14:08:00 → PDX 2026-12-30 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2026-12-30 18:15:00 → OGG 2026-12-30 22:23:00.

2026-12-28 → 2026-12-30 · Axel-exclusive $1032.76

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2026-12-30 09:20:00 → OGG 2026-12-30 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2026-12-31 · Axel-exclusive $850.50

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2026-12-31 14:08:00 → OGG 2026-12-31 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2026-12-31 14:08:00 → PDX 2026-12-31 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2026-12-31 18:15:00 → OGG 2026-12-31 22:23:00.

2026-12-28 → 2026-12-31 · Axel-exclusive $1032.76

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2026-12-31 09:20:00 → OGG 2026-12-31 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2027-01-01 · Axel-exclusive $850.50

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-01 14:08:00 → OGG 2027-01-01 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-01 14:08:00 → PDX 2027-01-01 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-01 18:15:00 → OGG 2027-01-01 22:23:00.

2026-12-28 → 2027-01-01 · Axel-exclusive $1032.76

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2027-01-01 09:20:00 → OGG 2027-01-01 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2027-01-02 · Axel-exclusive $850.50

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-02 14:08:00 → OGG 2027-01-02 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-02 14:08:00 → PDX 2027-01-02 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-02 18:15:00 → OGG 2027-01-02 22:23:00.

2026-12-28 → 2027-01-02 · Axel-exclusive $1005.76

• American Airlines AA88: OGG 2026-12-28 19:04:00 → ORD 2026-12-29 07:20:00; nonstop; 496 minutes. Local airport times.
• American Airlines AA89: ORD 2027-01-02 11:40:00 → OGG 2027-01-02 16:26:00; nonstop; 526 minutes. Local airport times.

2026-12-28 → 2027-01-03 · Axel-exclusive $850.50

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-03 14:08:00 → OGG 2027-01-03 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-03 14:08:00 → PDX 2027-01-03 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-03 18:15:00 → OGG 2027-01-03 22:23:00.

2026-12-28 → 2027-01-03 · Axel-exclusive $1005.76

• American Airlines AA88: OGG 2026-12-28 19:04:00 → ORD 2026-12-29 07:20:00; nonstop; 496 minutes. Local airport times.
• American Airlines AA89: ORD 2027-01-03 12:30:00 → OGG 2027-01-03 17:34:00; nonstop; 544 minutes. Local airport times.

2026-12-28 → 2027-01-05 · Axel-exclusive $850.50

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-05 14:08:00 → OGG 2027-01-05 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-05 14:08:00 → PDX 2027-01-05 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-05 18:15:00 → OGG 2027-01-05 22:23:00.

2026-12-28 → 2027-01-05 · Axel-exclusive $1032.76

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2027-01-05 09:20:00 → OGG 2027-01-05 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2027-01-06 · Axel-exclusive $740.25

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-06 14:08:00 → OGG 2027-01-06 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-06 14:08:00 → PDX 2027-01-06 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-06 18:15:00 → OGG 2027-01-06 22:23:00.

2026-12-28 → 2027-01-06 · Axel-exclusive $898.88

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2027-01-06 09:20:00 → OGG 2027-01-06 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2027-01-07 · Axel-exclusive $740.25

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-07 14:08:00 → OGG 2027-01-07 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-07 14:08:00 → PDX 2027-01-07 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-07 18:15:00 → OGG 2027-01-07 22:23:00.

2026-12-28 → 2027-01-07 · Axel-exclusive $898.88

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2027-01-07 09:20:00 → OGG 2027-01-07 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2027-01-08 · Axel-exclusive $740.25

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-08 14:08:00 → OGG 2027-01-08 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-08 14:08:00 → PDX 2027-01-08 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-08 18:15:00 → OGG 2027-01-08 22:23:00.

2026-12-28 → 2027-01-08 · Axel-exclusive $898.88

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2027-01-08 09:20:00 → OGG 2027-01-08 14:40:00; nonstop; 560 minutes. Local airport times.

2026-12-28 → 2027-01-09 · Axel-exclusive $740.25

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-09 14:08:00 → OGG 2027-01-09 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-09 14:08:00 → PDX 2027-01-09 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-09 18:15:00 → OGG 2027-01-09 22:23:00.

2026-12-28 → 2027-01-09 · Axel-exclusive $875.38

• American Airlines AA88: OGG 2026-12-28 19:04:00 → ORD 2026-12-29 07:20:00; nonstop; 496 minutes. Local airport times.
• American Airlines AA89: ORD 2027-01-09 11:40:00 → OGG 2027-01-09 16:26:00; nonstop; 526 minutes. Local airport times.

2026-12-28 → 2027-01-11 · Axel-exclusive $740.25

• Alaska Airlines AS934 / AA2664: OGG 2026-12-28 14:12:00 → ORD 2026-12-29 05:01:00; 1 stop(s) via LAX; 649 minutes. Local airport times.
  • AS934: OGG 2026-12-28 14:12:00 → LAX 2026-12-28 21:22:00; layover at LAX: 97 minutes.
  • AA2664: LAX 2026-12-28 22:59:00 → ORD 2026-12-29 05:01:00.
• Alaska Airlines AS325 / AS353: ORD 2027-01-11 14:08:00 → OGG 2027-01-11 22:23:00; 1 stop(s) via PDX; 735 minutes. Local airport times.
  • AS325: ORD 2027-01-11 14:08:00 → PDX 2027-01-11 16:58:00; layover at PDX: 77 minutes.
  • AS353: PDX 2027-01-11 18:15:00 → OGG 2027-01-11 22:23:00.

2026-12-28 → 2027-01-11 · Axel-exclusive $898.88

• United Airlines UA203: OGG 2026-12-28 17:05:00 → ORD 2026-12-29 05:03:00; nonstop; 478 minutes. Local airport times.
• United Airlines UA202: ORD 2027-01-11 09:20:00 → OGG 2027-01-11 14:40:00; nonstop; 560 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 27, 2026 · Return options
• Dec 29, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Kahului (OGG) to Chicago (ORD) · Dec 28, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals 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 the time its price was issued); 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 Maui to Chicago (ORD) 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