Portland (PDX) to Chicago (ORD), Nov 20–24, 2026: from $416 round trip

Portland (PDX) to Chicago (ORD), Nov 20–24, 2026: from $416 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $416 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Nov 20–24, 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 20–24, 2026 · 4 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

2026-11-20 → 2026-11-24 · Axel-exclusive $423.00

• Alaska Airlines AS324: PDX 2026-11-20 07:00:00 → ORD 2026-11-20 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-11-24 14:08:00 → PDX 2026-11-24 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $434.75

• American Airlines AA3329: PDX 2026-11-20 23:13:00 → ORD 2026-11-21 05:07:00; nonstop; 234 minutes. Local airport times.
• American Airlines AA519: ORD 2026-11-24 17:05:00 → PDX 2026-11-24 19:47:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $458.25

• United Airlines UA1923: PDX 2026-11-20 10:43:00 → ORD 2026-11-20 16:49:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-11-24 19:45:00 → PDX 2026-11-24 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $434.75

• American Airlines AA563: PDX 2026-11-20 13:46:00 → ORD 2026-11-20 20:00:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA519: ORD 2026-11-24 17:05:00 → PDX 2026-11-24 19:47:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $458.25

• United Airlines UA2266: PDX 2026-11-20 14:34:00 → ORD 2026-11-20 20:40:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-11-24 19:45:00 → PDX 2026-11-24 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $416.25

• Alaska Airlines AS324: PDX 2026-11-20 07:01:00 → ORD 2026-11-20 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-11-24 15:19:00 → PDX 2026-11-24 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-11-24 15:19:00 → SEA 2026-11-24 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-11-24 19:54:00 → PDX 2026-11-24 20:50:00.

2026-11-20 → 2026-11-24 · Axel-exclusive $418.00

• Alaska Airlines AS250 / AA677: PDX 2026-11-20 10:30:00 → ORD 2026-11-20 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-20 10:30:00 → GEG 2026-11-20 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-20 14:13:00 → ORD 2026-11-20 20:07:00.
• Alaska Airlines AS325: ORD 2026-11-24 14:08:00 → PDX 2026-11-24 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $418.00

• Alaska Airlines AS3355 / AA3186: PDX 2026-11-20 07:16:00 → ORD 2026-11-20 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-11-20 07:16:00 → SLC 2026-11-20 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-11-20 11:37:00 → ORD 2026-11-20 16:00:00.
• Alaska Airlines AS325: ORD 2026-11-24 14:08:00 → PDX 2026-11-24 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $419.75

• American Airlines AA2496 / AA2221: PDX 2026-11-20 14:36:00 → ORD 2026-11-20 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-11-20 14:36:00 → DFW 2026-11-20 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-11-20 21:30:00 → ORD 2026-11-20 23:59:00.
• American Airlines AA519: ORD 2026-11-24 17:05:00 → PDX 2026-11-24 19:47:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $443.25

• United Airlines UA1292 / UA1958: PDX 2026-11-20 15:44:00 → ORD 2026-11-21 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-20 15:44:00 → SFO 2026-11-20 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-20 18:42:00 → ORD 2026-11-21 00:59:00.
• United Airlines UA1786: ORD 2026-11-24 19:45:00 → PDX 2026-11-24 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-20 → 2026-11-24 · Axel-exclusive $443.25

• United Airlines UA459 / UA2329: PDX 2026-11-20 05:00:00 → ORD 2026-11-20 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-11-20 05:00:00 → DEN 2026-11-20 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-11-20 09:55:00 → ORD 2026-11-20 13:35:00.
• United Airlines UA1786: ORD 2026-11-24 19:45:00 → PDX 2026-11-24 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 19, 2026 · Return options
• Nov 21, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Nov 20, 2026 · return Nov 24, 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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