Portland (PDX) to Chicago (ORD) · Jan 4, 2027 · return Jan 9, 2027

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 (Jan 4–9, 2027 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $485 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $564 total · 5★ Nobu Hotel Chicago, $1,771 total

All hotels in Chicago

Route overview: Portland to Chicago (ORD) flight deals

2027-01-04 → 2027-01-09 · Axel-exclusive $383.40

• Alaska Airlines AS324: PDX 2027-01-04 07:00:00 → ORD 2027-01-04 13:10:00; nonstop; 250 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-09 14:08:00 → PDX 2027-01-09 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $394.05

• American Airlines AA3329: PDX 2027-01-04 23:31:00 → ORD 2027-01-05 05:25:00; nonstop; 234 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-09 10:05:00 → PDX 2027-01-09 13:01:00; nonstop; 296 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $415.35

• United Airlines UA2306: PDX 2027-01-04 07:02:00 → ORD 2027-01-04 13:06:00; nonstop; 244 minutes. Local airport times.
• United Airlines UA2243: ORD 2027-01-09 19:57:00 → PDX 2027-01-09 22:47:00; nonstop; 290 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $409.45

• Delta Air Lines DL1203 / DL2377: PDX 2027-01-04 09:59:00 → ORD 2027-01-04 18:06:00; 1 stop(s) via SLC; 367 minutes. Local airport times.
  • DL1203: PDX 2027-01-04 09:59:00 → SLC 2027-01-04 12:53:00; layover at SLC: 62 minutes.
  • DL2377: SLC 2027-01-04 13:55:00 → ORD 2027-01-04 18:06:00.
• United Airlines UA2243: ORD 2027-01-09 19:57:00 → PDX 2027-01-09 22:47:00; nonstop; 290 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $394.05

• American Airlines AA563: PDX 2027-01-04 13:46:00 → ORD 2027-01-04 20:00:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-09 10:05:00 → PDX 2027-01-09 13:01:00; nonstop; 296 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $415.35

• United Airlines UA2094: PDX 2027-01-04 23:50:00 → ORD 2027-01-05 05:59:00; nonstop; 249 minutes. Local airport times.
• United Airlines UA2243: ORD 2027-01-09 19:57:00 → PDX 2027-01-09 22:47:00; nonstop; 290 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $376.35

• American Airlines AA2496 / AA2221: PDX 2027-01-04 14:36:00 → ORD 2027-01-04 23:59:00; 1 stop(s) via DFW; 443 minutes. Local airport times.
  • AA2496: PDX 2027-01-04 14:36:00 → DFW 2027-01-04 20:28:00; layover at DFW: 62 minutes.
  • AA2221: DFW 2027-01-04 21:30:00 → ORD 2027-01-04 23:59:00.
• American Airlines AA563: ORD 2027-01-09 10:05:00 → PDX 2027-01-09 13:01:00; nonstop; 296 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $377.50

• Alaska Airlines AS3355 / AA3186: PDX 2027-01-04 07:16:00 → ORD 2027-01-04 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2027-01-04 07:16:00 → SLC 2027-01-04 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2027-01-04 11:37:00 → ORD 2027-01-04 16:00:00.
• Alaska Airlines AS325: ORD 2027-01-09 14:08:00 → PDX 2027-01-09 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $378.65

• Alaska Airlines AS324: PDX 2027-01-04 07:00:00 → ORD 2027-01-04 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-09 15:19:00 → PDX 2027-01-09 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-09 15:19:00 → SEA 2027-01-09 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-09 19:54:00 → PDX 2027-01-09 20:50:00.

2027-01-04 → 2027-01-09 · Axel-exclusive $397.65

• United Airlines UA459 / UA2329: PDX 2027-01-04 05:00:00 → ORD 2027-01-04 13:35:00; 1 stop(s) via DEN; 395 minutes. Local airport times.
  • UA459: PDX 2027-01-04 05:00:00 → DEN 2027-01-04 08:28:00; layover at DEN: 87 minutes.
  • UA2329: DEN 2027-01-04 09:55:00 → ORD 2027-01-04 13:35:00.
• United Airlines UA2243: ORD 2027-01-09 19:57:00 → PDX 2027-01-09 22:47:00; nonstop; 290 minutes. Local airport times.

2027-01-04 → 2027-01-09 · Axel-exclusive $397.65

• United Airlines UA1292 / UA1958: PDX 2027-01-04 15:44:00 → ORD 2027-01-05 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2027-01-04 15:44:00 → SFO 2027-01-04 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2027-01-04 18:42:00 → ORD 2027-01-05 00:59:00.
• United Airlines UA2243: ORD 2027-01-09 19:57:00 → PDX 2027-01-09 22:47:00; nonstop; 290 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 3, 2027 · Return options
• Jan 5, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Jan 4, 2027 · return Jan 9, 2027: 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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