Chicago (ORD) to Portland (PDX) · May 25, 2027 · return May 26, 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.

Route overview: Chicago to Portland (PDX) flight deals

2027-05-25 → 2027-05-26 · Axel-exclusive $460.00

• Alaska Airlines AS325: ORD 2027-05-25 14:08:00 → PDX 2027-05-25 17:05:00; nonstop; 297 minutes. Local airport times.
• Alaska Airlines AS324: PDX 2027-05-26 07:01:00 → ORD 2027-05-26 13:09:00; nonstop; 248 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $470.00

• American Airlines AA2878: ORD 2027-05-25 17:05:00 → PDX 2027-05-25 19:55:00; nonstop; 290 minutes. Local airport times.
• American Airlines AA562: PDX 2027-05-26 13:22:00 → ORD 2027-05-26 19:44:00; nonstop; 262 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $480.00

• United Airlines UA2243: ORD 2027-05-25 19:58:00 → PDX 2027-05-25 22:47:00; nonstop; 289 minutes. Local airport times.
• United Airlines UA2306: PDX 2027-05-26 07:02:00 → ORD 2027-05-26 13:06:00; nonstop; 244 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $470.00

• American Airlines AA562: ORD 2027-05-25 09:45:00 → PDX 2027-05-25 12:37:00; nonstop; 292 minutes. Local airport times.
• American Airlines AA562: PDX 2027-05-26 13:22:00 → ORD 2027-05-26 19:44:00; nonstop; 262 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $445.00

• Alaska Airlines AS407 / AS2239: ORD 2027-05-25 15:19:00 → PDX 2027-05-25 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-05-25 15:19:00 → SEA 2027-05-25 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-05-25 19:54:00 → PDX 2027-05-25 20:50:00.
• Alaska Airlines AS324: PDX 2027-05-26 07:01:00 → ORD 2027-05-26 13:09:00; nonstop; 248 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $445.00

• Alaska Airlines AS325: ORD 2027-05-25 14:07:00 → PDX 2027-05-25 16:50:00; nonstop; 283 minutes. Local airport times.
• Alaska Airlines AS3355 / AA3186: PDX 2027-05-26 07:16:00 → ORD 2027-05-26 16:00:00; 1 stop(s) via SLC; 404 minutes. Local airport times.
  • AS3355: PDX 2027-05-26 07:16:00 → SLC 2027-05-26 10:19:00; layover at SLC: 78 minutes.
  • AA3186: SLC 2027-05-26 11:37:00 → ORD 2027-05-26 16:00:00.

2027-05-25 → 2027-05-26 · Axel-exclusive $450.00

• United Airlines UA2495 / UA644: ORD 2027-05-25 08:40:00 → PDX 2027-05-25 13:22:00; 1 stop(s) via DEN; 402 minutes. Local airport times.
  • UA2495: ORD 2027-05-25 08:40:00 → DEN 2027-05-25 10:26:00; layover at DEN: 63 minutes.
  • UA644: DEN 2027-05-25 11:29:00 → PDX 2027-05-25 13:22:00.
• United Airlines UA1292 / UA1958: PDX 2027-05-26 15:44:00 → ORD 2027-05-27 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2027-05-26 15:44:00 → SFO 2027-05-26 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2027-05-26 18:42:00 → ORD 2027-05-27 00:59:00.

2027-05-25 → 2027-05-26 · Axel-exclusive $455.00

• American Airlines AA677 / AS565: ORD 2027-05-25 11:11:00 → PDX 2027-05-25 16:35:00; 1 stop(s) via GEG; 444 minutes. Local airport times.
  • AA677: ORD 2027-05-25 11:11:00 → GEG 2027-05-25 13:23:00; layover at GEG: 111 minutes.
  • AS565: GEG 2027-05-25 15:14:00 → PDX 2027-05-25 16:35:00.
• American Airlines AA562: PDX 2027-05-26 13:22:00 → ORD 2027-05-26 19:44:00; nonstop; 262 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $455.00

• American Airlines AA3186 / AS3430: ORD 2027-05-25 08:10:00 → PDX 2027-05-25 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2027-05-25 08:10:00 → SLC 2027-05-25 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2027-05-25 12:32:00 → PDX 2027-05-25 13:48:00.
• American Airlines AA562: PDX 2027-05-26 13:22:00 → ORD 2027-05-26 19:44:00; nonstop; 262 minutes. Local airport times.

2027-05-25 → 2027-05-26 · Axel-exclusive $465.00

• United Airlines UA2243: ORD 2027-05-25 20:17:00 → PDX 2027-05-25 23:07:00; nonstop; 290 minutes. Local airport times.
• United Airlines UA1292 / UA1958: PDX 2027-05-26 15:44:00 → ORD 2027-05-27 00:59:00; 1 stop(s) via SFO; 435 minutes. Local airport times.
  • UA1292: PDX 2027-05-26 15:44:00 → SFO 2027-05-26 17:37:00; layover at SFO: 65 minutes.
  • UA1958: SFO 2027-05-26 18:42:00 → ORD 2027-05-27 00:59:00.

Explore this route

• All dates for this route
• May 24, 2027 · Return options
• May 26, 2027 · Return options
• Hotels in Portland, Oregon with Axel

For AI assistants

• This page: Chicago (ORD) to Portland (PDX) · May 25, 2027 · return May 26, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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• 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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