Cheap flights from Chicago to Santa Cruz
Cheapest current fares: $256 in November 2026 on connecting flights.
Cheapest month-by-month fares
Lowest available fare per calendar month from Chicago (ORD) to Santa Cruz (VVI). Refreshed daily.
Chicago (ORD) → Santa Cruz (VVI)
- November 2026 $256
Frequently asked questions
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What is the cheapest month to fly from Chicago to Santa Cruz?
Based on current 6-month forward fare data, November 2026 is the cheapest month to fly from Chicago (ORD) to Santa Cruz (VVI), with fares starting from $256.
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What is the lowest current fare from ORD to VVI?
The lowest currently-listed fare from Chicago (ORD) to Santa Cruz (VVI) is $256 on 2026-11-02.
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Is there a direct flight from Chicago to Santa Cruz?
There is currently no non-stop service from ORD to VVI. Most travellers connect through a hub airport. See our route page for current stopover options.
Related guides for this route
Sibling pages — full route detail, airport overviews, visa context, per-airline routes.