Flights from Anchorage to the Midwest for 4 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 · $356.25

• United Airlines UA267: ANC 2026-11-20 20:45:00 → ORD 2026-11-21 05:59:00; nonstop; 374 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $607.50

• United Airlines UA267: ANC 2026-11-27 20:45:00 → ORD 2026-11-28 05:59:00; nonstop; 374 minutes. Local airport times.
• United Airlines UA1892: ORD 2026-12-04 15:30:00 → ANC 2026-12-04 19:23:00; nonstop; 413 minutes. Local airport times.

2026-11-20 · one way · $306.25

• Alaska Airlines AS766 / AS328: ANC 2026-11-20 16:18:00 → ORD 2026-11-21 05:37:00; 1 stop(s) via SEA; 619 minutes. Local airport times.
  • AS766: ANC 2026-11-20 16:18:00 → SEA 2026-11-20 20:50:00; layover at SEA: 170 minutes.
  • AS328: SEA 2026-11-20 23:40:00 → ORD 2026-11-21 05:37:00.

2026-11-20 · one way · $331.25

• Delta Air Lines DL377 / DL1810: ANC 2026-11-20 21:50:00 → ORD 2026-11-21 09:04:00; 1 stop(s) via MSP; 494 minutes. Local airport times.
  • DL377: ANC 2026-11-20 21:50:00 → MSP 2026-11-21 06:13:00; layover at MSP: 62 minutes.
  • DL1810: MSP 2026-11-21 07:15:00 → ORD 2026-11-21 09:04:00.

2026-11-27 → 2026-12-04 · $517.50

• Alaska Airlines AS1501 / AA562: ANC 2026-11-27 07:00:00 → ORD 2026-11-27 19:44:00; 1 stop(s) via PDX; 584 minutes. Local airport times.
  • AS1501: ANC 2026-11-27 07:00:00 → PDX 2026-11-27 11:36:00; layover at PDX: 114 minutes.
  • AA562: PDX 2026-11-27 13:30:00 → ORD 2026-11-27 19:44:00.
• Alaska Airlines AS583 / AS99: ORD 2026-12-04 09:00:00 → ANC 2026-12-04 16:47:00; 1 stop(s) via SEA; 647 minutes. Local airport times.
  • AS583: ORD 2026-12-04 09:00:00 → SEA 2026-12-04 12:00:00; layover at SEA: 120 minutes.
  • AS99: SEA 2026-12-04 14:00:00 → ANC 2026-12-04 16:47:00.

2026-11-27 → 2026-12-04 · $562.50

• Delta Air Lines DL377 / DL1810: ANC 2026-11-27 21:50:00 → ORD 2026-11-28 09:04:00; 1 stop(s) via MSP; 494 minutes. Local airport times.
  • DL377: ANC 2026-11-27 21:50:00 → MSP 2026-11-28 06:13:00; layover at MSP: 62 minutes.
  • DL1810: MSP 2026-11-28 07:15:00 → ORD 2026-11-28 09:04:00.
• Delta Air Lines DL2041 / DL922: ORD 2026-12-04 06:40:00 → ANC 2026-12-04 13:26:00; 1 stop(s) via SEA; 586 minutes. Local airport times.
  • DL2041: ORD 2026-12-04 06:40:00 → SEA 2026-12-04 09:30:00; layover at SEA: 65 minutes.
  • DL922: SEA 2026-12-04 10:35:00 → ANC 2026-12-04 13:26:00.

2026-11-20 → 2026-11-23 · $675.00

• United Airlines UA267: ANC 2026-11-20 20:45:00 → ORD 2026-11-21 05:59:00; nonstop; 374 minutes. Local airport times.
• United Airlines UA1892: ORD 2026-11-23 15:30:00 → ANC 2026-11-23 19:23:00; nonstop; 413 minutes. Local airport times.

2026-11-20 · one way · $306.25

• Alaska Airlines AS1501 / AA562: ANC 2026-11-20 07:00:00 → ORD 2026-11-20 19:44:00; 1 stop(s) via PDX; 584 minutes. Local airport times.
  • AS1501: ANC 2026-11-20 07:00:00 → PDX 2026-11-20 11:36:00; layover at PDX: 114 minutes.
  • AA562: PDX 2026-11-20 13:30:00 → ORD 2026-11-20 19:44:00.

2026-11-20 · one way · $306.25

• Alaska Airlines AS760 / AA3216: ANC 2026-11-20 23:05:00 → ORD 2026-11-21 12:35:00; 1 stop(s) via LAS; 630 minutes. Local airport times.
  • AS760: ANC 2026-11-20 23:05:00 → LAS 2026-11-21 05:15:00; layover at LAS: 96 minutes.
  • AA3216: LAS 2026-11-21 06:51:00 → ORD 2026-11-21 12:35:00.

2026-11-20 · one way · $318.75

• United Airlines UA1959 / UA2329: ANC 2026-11-20 00:07:00 → ORD 2026-11-20 13:35:00; 1 stop(s) via DEN; 628 minutes. Local airport times.
  • UA1959: ANC 2026-11-20 00:07:00 → DEN 2026-11-20 07:23:00; layover at DEN: 152 minutes.
  • UA2329: DEN 2026-11-20 09:55:00 → ORD 2026-11-20 13:35:00.

2026-11-20 · one way · $331.25

• Delta Air Lines DL925 / DL2055: ANC 2026-11-20 01:15:00 → ORD 2026-11-20 13:30:00; 1 stop(s) via SEA; 555 minutes. Local airport times.
  • DL925: ANC 2026-11-20 01:15:00 → SEA 2026-11-20 05:58:00; layover at SEA: 82 minutes.
  • DL2055: SEA 2026-11-20 07:20:00 → ORD 2026-11-20 13:30:00.

2026-11-27 → 2026-12-04 · $517.50

• Alaska Airlines AS760 / AA3216: ANC 2026-11-27 23:05:00 → ORD 2026-11-28 12:35:00; 1 stop(s) via LAS; 630 minutes. Local airport times.
  • AS760: ANC 2026-11-27 23:05:00 → LAS 2026-11-28 05:15:00; layover at LAS: 96 minutes.
  • AA3216: LAS 2026-11-28 06:51:00 → ORD 2026-11-28 12:35:00.
• Alaska Airlines AS583 / AS99: ORD 2026-12-04 09:00:00 → ANC 2026-12-04 16:47:00; 1 stop(s) via SEA; 647 minutes. Local airport times.
  • AS583: ORD 2026-12-04 09:00:00 → SEA 2026-12-04 12:00:00; layover at SEA: 120 minutes.
  • AS99: SEA 2026-12-04 14:00:00 → ANC 2026-12-04 16:47:00.

2026-11-27 → 2026-12-04 · $517.50

• Alaska Airlines AS766 / AS328: ANC 2026-11-27 16:18:00 → ORD 2026-11-28 05:37:00; 1 stop(s) via SEA; 619 minutes. Local airport times.
  • AS766: ANC 2026-11-27 16:18:00 → SEA 2026-11-27 20:50:00; layover at SEA: 170 minutes.
  • AS328: SEA 2026-11-27 23:40:00 → ORD 2026-11-28 05:37:00.
• Alaska Airlines AS583 / AS99: ORD 2026-12-04 09:00:00 → ANC 2026-12-04 16:47:00; 1 stop(s) via SEA; 647 minutes. Local airport times.
  • AS583: ORD 2026-12-04 09:00:00 → SEA 2026-12-04 12:00:00; layover at SEA: 120 minutes.
  • AS99: SEA 2026-12-04 14:00:00 → ANC 2026-12-04 16:47:00.

2026-11-27 → 2026-12-04 · $562.50

• Delta Air Lines DL925 / DL2055: ANC 2026-11-27 01:15:00 → ORD 2026-11-27 13:30:00; 1 stop(s) via SEA; 555 minutes. Local airport times.
  • DL925: ANC 2026-11-27 01:15:00 → SEA 2026-11-27 05:58:00; layover at SEA: 82 minutes.
  • DL2055: SEA 2026-11-27 07:20:00 → ORD 2026-11-27 13:30:00.
• Delta Air Lines DL2041 / DL922: ORD 2026-12-04 06:40:00 → ANC 2026-12-04 13:26:00; 1 stop(s) via SEA; 586 minutes. Local airport times.
  • DL2041: ORD 2026-12-04 06:40:00 → SEA 2026-12-04 09:30:00; layover at SEA: 65 minutes.
  • DL922: SEA 2026-12-04 10:35:00 → ANC 2026-12-04 13:26:00.

2026-11-27 → 2026-12-04 · $570.00

• United Airlines UA1959 / UA2329: ANC 2026-11-27 00:07:00 → ORD 2026-11-27 13:35:00; 1 stop(s) via DEN; 628 minutes. Local airport times.
  • UA1959: ANC 2026-11-27 00:07:00 → DEN 2026-11-27 07:23:00; layover at DEN: 152 minutes.
  • UA2329: DEN 2026-11-27 09:55:00 → ORD 2026-11-27 13:35:00.
• United Airlines UA1892: ORD 2026-12-04 15:30:00 → ANC 2026-12-04 19:23:00; nonstop; 413 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $575.00

• Alaska Airlines AS1501 / AA562: ANC 2026-11-20 07:00:00 → ORD 2026-11-20 19:44:00; 1 stop(s) via PDX; 584 minutes. Local airport times.
  • AS1501: ANC 2026-11-20 07:00:00 → PDX 2026-11-20 11:36:00; layover at PDX: 114 minutes.
  • AA562: PDX 2026-11-20 13:30:00 → ORD 2026-11-20 19:44:00.
• Alaska Airlines AS583 / AS99: ORD 2026-11-23 09:00:00 → ANC 2026-11-23 16:47:00; 1 stop(s) via SEA; 647 minutes. Local airport times.
  • AS583: ORD 2026-11-23 09:00:00 → SEA 2026-11-23 12:00:00; layover at SEA: 120 minutes.
  • AS99: SEA 2026-11-23 14:00:00 → ANC 2026-11-23 16:47:00.

2026-11-20 → 2026-11-23 · $575.00

• Alaska Airlines AS766 / AS328: ANC 2026-11-20 16:18:00 → ORD 2026-11-21 05:37:00; 1 stop(s) via SEA; 619 minutes. Local airport times.
  • AS766: ANC 2026-11-20 16:18:00 → SEA 2026-11-20 20:50:00; layover at SEA: 170 minutes.
  • AS328: SEA 2026-11-20 23:40:00 → ORD 2026-11-21 05:37:00.
• Alaska Airlines AS583 / AS99: ORD 2026-11-23 09:00:00 → ANC 2026-11-23 16:47:00; 1 stop(s) via SEA; 647 minutes. Local airport times.
  • AS583: ORD 2026-11-23 09:00:00 → SEA 2026-11-23 12:00:00; layover at SEA: 120 minutes.
  • AS99: SEA 2026-11-23 14:00:00 → ANC 2026-11-23 16:47:00.

2026-11-20 → 2026-11-23 · $575.00

• Alaska Airlines AS760 / AA3216: ANC 2026-11-20 23:05:00 → ORD 2026-11-21 12:35:00; 1 stop(s) via LAS; 630 minutes. Local airport times.
  • AS760: ANC 2026-11-20 23:05:00 → LAS 2026-11-21 05:15:00; layover at LAS: 96 minutes.
  • AA3216: LAS 2026-11-21 06:51:00 → ORD 2026-11-21 12:35:00.
• Alaska Airlines AS583 / AS99: ORD 2026-11-23 09:00:00 → ANC 2026-11-23 16:47:00; 1 stop(s) via SEA; 647 minutes. Local airport times.
  • AS583: ORD 2026-11-23 09:00:00 → SEA 2026-11-23 12:00:00; layover at SEA: 120 minutes.
  • AS99: SEA 2026-11-23 14:00:00 → ANC 2026-11-23 16:47:00.

2026-11-20 → 2026-11-23 · $625.00

• Delta Air Lines DL925 / DL2055: ANC 2026-11-20 01:15:00 → ORD 2026-11-20 13:30:00; 1 stop(s) via SEA; 555 minutes. Local airport times.
  • DL925: ANC 2026-11-20 01:15:00 → SEA 2026-11-20 05:58:00; layover at SEA: 82 minutes.
  • DL2055: SEA 2026-11-20 07:20:00 → ORD 2026-11-20 13:30:00.
• Delta Air Lines DL2041 / DL922: ORD 2026-11-23 06:40:00 → ANC 2026-11-23 13:26:00; 1 stop(s) via SEA; 586 minutes. Local airport times.
  • DL2041: ORD 2026-11-23 06:40:00 → SEA 2026-11-23 09:30:00; layover at SEA: 65 minutes.
  • DL922: SEA 2026-11-23 10:35:00 → ANC 2026-11-23 13:26:00.

2026-11-20 → 2026-11-23 · $625.00

• Delta Air Lines DL377 / DL1810: ANC 2026-11-20 21:50:00 → ORD 2026-11-21 09:04:00; 1 stop(s) via MSP; 494 minutes. Local airport times.
  • DL377: ANC 2026-11-20 21:50:00 → MSP 2026-11-21 06:13:00; layover at MSP: 62 minutes.
  • DL1810: MSP 2026-11-21 07:15:00 → ORD 2026-11-21 09:04:00.
• Delta Air Lines DL2041 / DL922: ORD 2026-11-23 06:40:00 → ANC 2026-11-23 13:26:00; 1 stop(s) via SEA; 586 minutes. Local airport times.
  • DL2041: ORD 2026-11-23 06:40:00 → SEA 2026-11-23 09:30:00; layover at SEA: 65 minutes.
  • DL922: SEA 2026-11-23 10:35:00 → ANC 2026-11-23 13:26:00.

2026-11-20 → 2026-11-23 · $637.50

• United Airlines UA1959 / UA2329: ANC 2026-11-20 00:07:00 → ORD 2026-11-20 13:35:00; 1 stop(s) via DEN; 628 minutes. Local airport times.
  • UA1959: ANC 2026-11-20 00:07:00 → DEN 2026-11-20 07:23:00; layover at DEN: 152 minutes.
  • UA2329: DEN 2026-11-20 09:55:00 → ORD 2026-11-20 13:35:00.
• United Airlines UA1892: ORD 2026-11-23 15:30:00 → ANC 2026-11-23 19:23:00; nonstop; 413 minutes. Local airport times.

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 4 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

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