Portland (PDX) to Chicago (ORD), Nov 25–27, 2026: from $473 round trip

Portland (PDX) to Chicago (ORD), Nov 25–27, 2026: from $473 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $473 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Nov 25–27, 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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

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 (Nov 25–27, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

Route overview: Portland to Chicago (ORD) flight deals

2026-11-25 → 2026-11-27 · Axel-exclusive $486.00

• Alaska Airlines AS324: PDX 2026-11-25 07:00:00 → ORD 2026-11-25 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-11-27 14:08:00 → PDX 2026-11-27 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $499.50

• American Airlines AA519: PDX 2026-11-25 23:09:00 → ORD 2026-11-26 05:07:00; nonstop; 238 minutes. Local airport times.
• American Airlines AA561: ORD 2026-11-27 09:44:00 → PDX 2026-11-27 12:26:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $526.50

• United Airlines UA2822: PDX 2026-11-25 14:26:00 → ORD 2026-11-25 20:28:00; nonstop; 242 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-11-27 19:45:00 → PDX 2026-11-27 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $499.50

• American Airlines AA562: PDX 2026-11-25 13:22:00 → ORD 2026-11-25 19:44:00; nonstop; 262 minutes. Local airport times.
• American Airlines AA561: ORD 2026-11-27 09:44:00 → PDX 2026-11-27 12:26:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $526.50

• United Airlines UA1923: PDX 2026-11-25 10:47:00 → ORD 2026-11-25 16:53:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-11-27 19:45:00 → PDX 2026-11-27 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $472.50

• Alaska Airlines AS250 / AA677: PDX 2026-11-25 10:30:00 → ORD 2026-11-25 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-25 10:30:00 → GEG 2026-11-25 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-25 14:13:00 → ORD 2026-11-25 20:07:00.
• Alaska Airlines AS407 / AS2239: ORD 2026-11-27 15:19:00 → PDX 2026-11-27 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-11-27 15:19:00 → SEA 2026-11-27 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-11-27 19:54:00 → PDX 2026-11-27 20:50:00.

2026-11-25 → 2026-11-27 · Axel-exclusive $472.50

• Alaska Airlines AS3355 / AA3186: PDX 2026-11-25 07:16:00 → ORD 2026-11-25 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-11-25 07:16:00 → SLC 2026-11-25 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-11-25 11:37:00 → ORD 2026-11-25 16:00:00.
• Alaska Airlines AS407 / AS2239: ORD 2026-11-27 15:19:00 → PDX 2026-11-27 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-11-27 15:19:00 → SEA 2026-11-27 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-11-27 19:54:00 → PDX 2026-11-27 20:50:00.

2026-11-25 → 2026-11-27 · Axel-exclusive $479.25

• Alaska Airlines AS324: PDX 2026-11-25 07:01:00 → ORD 2026-11-25 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-11-27 15:19:00 → PDX 2026-11-27 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-11-27 15:19:00 → SEA 2026-11-27 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-11-27 19:54:00 → PDX 2026-11-27 20:50:00.

2026-11-25 → 2026-11-27 · Axel-exclusive $506.25

• United Airlines UA1923: PDX 2026-11-25 10:43:00 → ORD 2026-11-25 16:49:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1498 / AC8652: ORD 2026-11-27 08:58:00 → PDX 2026-11-27 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
  • UA1498: ORD 2026-11-27 08:58:00 → YVR 2026-11-27 12:45:00; layover at YVR: 100 minutes.
  • AC8652: YVR 2026-11-27 14:25:00 → PDX 2026-11-27 14:41:00.

2026-11-25 → 2026-11-27 · Axel-exclusive $506.25

• United Airlines UA1292 / UA1958: PDX 2026-11-25 15:44:00 → ORD 2026-11-26 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-25 15:44:00 → SFO 2026-11-25 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-25 18:42:00 → ORD 2026-11-26 00:59:00.
• United Airlines UA1786: ORD 2026-11-27 19:45:00 → PDX 2026-11-27 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-25 → 2026-11-27 · Axel-exclusive $506.25

• United Airlines UA459 / UA2329: PDX 2026-11-25 05:00:00 → ORD 2026-11-25 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-11-25 05:00:00 → DEN 2026-11-25 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-11-25 09:55:00 → ORD 2026-11-25 13:35:00.
• United Airlines UA1786: ORD 2026-11-27 19:45:00 → PDX 2026-11-27 22:27:00; nonstop; 282 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Nov 24, 2026 · Return options
• Nov 26, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Nov 25, 2026 · return Nov 27, 2026: 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.
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