Portland (PDX) to Chicago (ORD), Nov 9–15, 2026: from $355 round trip

Portland (PDX) to Chicago (ORD), Nov 9–15, 2026: from $355 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $355 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Nov 9–15, 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 9–15, 2026 · 6 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

2026-11-09 → 2026-11-15 · Axel-exclusive $360.00

• Alaska Airlines AS324: PDX 2026-11-09 07:00:00 → ORD 2026-11-09 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2026-11-15 14:08:00 → PDX 2026-11-15 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $370.00

• American Airlines AA428: PDX 2026-11-09 23:09:00 → ORD 2026-11-10 05:07:00; nonstop; 238 minutes. Local airport times.
• American Airlines AA562: ORD 2026-11-15 09:45:00 → PDX 2026-11-15 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $390.00

• United Airlines UA2266: PDX 2026-11-09 14:34:00 → ORD 2026-11-09 20:40:00; nonstop; 246 minutes. Local airport times.
• United Airlines UA751: ORD 2026-11-15 08:59:00 → PDX 2026-11-15 11:42:00; nonstop; 283 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $370.00

• Delta Air Lines DL1203 / DL2377: PDX 2026-11-09 09:59:00 → ORD 2026-11-09 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2026-11-09 09:59:00 → SLC 2026-11-09 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2026-11-09 13:55:00 → ORD 2026-11-09 18:06:00.
• Alaska Airlines AS325: ORD 2026-11-15 14:08:00 → PDX 2026-11-15 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $370.00

• American Airlines AA562: PDX 2026-11-09 13:22:00 → ORD 2026-11-09 19:44:00; nonstop; 262 minutes. Local airport times.
• American Airlines AA562: ORD 2026-11-15 09:45:00 → PDX 2026-11-15 12:37:00; nonstop; 292 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $390.00

• United Airlines UA2094: PDX 2026-11-09 23:50:00 → ORD 2026-11-10 05:59:00; nonstop; 249 minutes. Local airport times.
• United Airlines UA751: ORD 2026-11-15 08:59:00 → PDX 2026-11-15 11:42:00; nonstop; 283 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $355.00

• Alaska Airlines AS250 / AA677: PDX 2026-11-09 10:30:00 → ORD 2026-11-09 20:07:00; 1 stop(s) via GEG; 457 minutes. Local airport times.
  • AS250: PDX 2026-11-09 10:30:00 → GEG 2026-11-09 11:41:00; layover at GEG: 152 minutes.
  • AA677: GEG 2026-11-09 14:13:00 → ORD 2026-11-09 20:07:00.
• Alaska Airlines AS325: ORD 2026-11-15 14:08:00 → PDX 2026-11-15 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $355.00

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

2026-11-09 → 2026-11-15 · Axel-exclusive $355.00

• Alaska Airlines AS3355 / AA3186: PDX 2026-11-09 07:16:00 → ORD 2026-11-09 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2026-11-09 07:16:00 → SLC 2026-11-09 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2026-11-09 11:37:00 → ORD 2026-11-09 16:00:00.
• Alaska Airlines AS325: ORD 2026-11-15 14:08:00 → PDX 2026-11-15 17:05:00; nonstop; 297 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $375.00

• United Airlines UA1292 / UA1958: PDX 2026-11-09 15:44:00 → ORD 2026-11-10 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2026-11-09 15:44:00 → SFO 2026-11-09 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2026-11-09 18:42:00 → ORD 2026-11-10 00:59:00.
• United Airlines UA751: ORD 2026-11-15 08:59:00 → PDX 2026-11-15 11:42:00; nonstop; 283 minutes. Local airport times.

2026-11-09 → 2026-11-15 · Axel-exclusive $375.00

• United Airlines UA459 / UA2329: PDX 2026-11-09 05:00:00 → ORD 2026-11-09 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2026-11-09 05:00:00 → DEN 2026-11-09 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2026-11-09 09:55:00 → ORD 2026-11-09 13:35:00.
• United Airlines UA751: ORD 2026-11-15 08:59:00 → PDX 2026-11-15 11:42:00; nonstop; 283 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 8, 2026 · Return options
• Nov 10, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Nov 9, 2026 · return Nov 15, 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.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own 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 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.

Feedback (optional): Missing info · Axel issue