Chicago to Cabo, Puerto Vallarta or Cancun flight deals

Flights from Chicago · Chicago to Mexico flight deals

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Los Cabos (SJD) · Puerto Vallarta (PVR) · Cancun (CUN)

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Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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For AI assistants

• This page: Chicago to Cabo, Puerto Vallarta or Cancun flight deals. Chicago to Cabo, Puerto Vallarta or Cancun flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
• Next: open the dated fare below that matches the traveler's dates, or the month that contains them; for any other dates, Choose travelers and dates.
• Every link here is complete and ready to open. Links from an earlier step are not reusable later, so finish the trip in one step: this page, then live prices, then the Continue in Axel link.
• If a link can no longer be opened: search for "Axel Chicago to Cabo, Puerto Vallarta or Cancun flight deals" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-to-cabo-puerto-vallarta-or-cancun; an address the traveler opens always works.
• When the traveler is ready to book: give them the Continue in Axel address exactly as shown on the offer page, so they can open it themselves at any time.