Portland (PDX) to Chicago (ORD) · Nov 27, 2026 · return Dec 4, 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: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Nov 27 – Dec 4, 2026 · 7 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $865 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,285 total · 5★ Nobu Hotel Chicago, $2,905.50 total

All hotels in Chicago

Route overview: Portland to Chicago (ORD) flight deals

2026-11-27 → 2026-12-04 · Axel-exclusive $423.00

• Alaska Airlines AS324: PDX 2026-11-27 07:01:00 → ORD 2026-11-27 13:09:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-12-04 14:08:00 → PDX 2026-12-04 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $434.75

• American Airlines AA3329: PDX 2026-11-27 23:13:00 → ORD 2026-11-28 05:07:00; nonstop; 234 minutes. Local airport times.
• American Airlines AA562: ORD 2026-12-04 09:45:00 → PDX 2026-12-04 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $458.25

• United Airlines UA1923: PDX 2026-11-27 10:43:00 → ORD 2026-11-27 16:49:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-12-04 19:45:00 → PDX 2026-12-04 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $434.75

• American Airlines AA563: PDX 2026-11-27 13:46:00 → ORD 2026-11-27 20:00:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA562: ORD 2026-12-04 09:45:00 → PDX 2026-12-04 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $458.25

• United Airlines UA2822: PDX 2026-11-27 14:26:00 → ORD 2026-11-27 20:28:00; nonstop; 242 minutes. Local airport times.
• United Airlines UA1786: ORD 2026-12-04 19:45:00 → PDX 2026-12-04 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $411.25

• Alaska Airlines AS3355 / AA3186: PDX 2026-11-27 07:16:00 → ORD 2026-11-27 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-11-27 07:16:00 → SLC 2026-11-27 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-11-27 11:37:00 → ORD 2026-11-27 16:00:00.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-04 15:19:00 → PDX 2026-12-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-04 15:19:00 → SEA 2026-12-04 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-04 19:54:00 → PDX 2026-12-04 20:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $411.25

• Alaska Airlines AS250 / AA677: PDX 2026-11-27 10:30:00 → ORD 2026-11-27 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-27 10:30:00 → GEG 2026-11-27 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-27 14:13:00 → ORD 2026-11-27 20:07:00.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-04 15:19:00 → PDX 2026-12-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-04 15:19:00 → SEA 2026-12-04 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-04 19:54:00 → PDX 2026-12-04 20:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $414.50

• American Airlines AA2496 / AA2221: PDX 2026-11-27 14:36:00 → ORD 2026-11-27 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2026-11-27 14:36:00 → DFW 2026-11-27 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2026-11-27 21:30:00 → ORD 2026-11-27 23:59:00.
• American Airlines AA562: ORD 2026-12-04 09:45:00 → PDX 2026-12-04 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $418.00

• Alaska Airlines AS324: PDX 2026-11-27 07:00:00 → ORD 2026-11-27 13:08:00; nonstop; 248 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2026-12-04 15:19:00 → PDX 2026-12-04 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2026-12-04 15:19:00 → SEA 2026-12-04 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2026-12-04 19:54:00 → PDX 2026-12-04 20:50:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $438.00

• United Airlines UA1292 / UA1958: PDX 2026-11-27 15:44:00 → ORD 2026-11-28 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-27 15:44:00 → SFO 2026-11-27 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-27 18:42:00 → ORD 2026-11-28 00:59:00.
• United Airlines UA1786: ORD 2026-12-04 19:45:00 → PDX 2026-12-04 22:27:00; nonstop; 282 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $443.25

• United Airlines UA1923: PDX 2026-11-27 10:47:00 → ORD 2026-11-27 16:53:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA1498 / AC8652: ORD 2026-12-04 08:58:00 → PDX 2026-12-04 14:41:00; 1 stop(s) via YVR; 463 minutes. Local airport times.
  • UA1498: ORD 2026-12-04 08:58:00 → YVR 2026-12-04 12:45:00; layover at YVR: 100 minutes.
  • AC8652: YVR 2026-12-04 14:25:00 → PDX 2026-12-04 14:41:00.

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 26, 2026 · Return options
• Nov 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Nov 27, 2026 · return Dec 4, 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• 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 Portland 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.

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