Chicago to Santa Cruz flights (ORD → VVI)
Looking for Chicago to Santa Cruz flights? Cheapest round-trip I’ve found: US$568 on COPA, 1 stop(s), departing 2026-11-04. That’s US$42 below the typical price for this route. Cheap flights from Chicago to Santa Cruz change daily — I re-check this route three times a day.
Deal score: Not enough data yet
1stops
13h 3mflight time
Nov 2026cheapest departure window
US$610typical price
Best months to fly Chicago to Santa Cruz
| Month | Cheapest seen |
|---|---|
| November | US$568 |
How to book this fare
I don’t sell tickets — I track prices and point you to where to look. To book Chicago to Santa Cruz flights:
- Search Chicago to Santa Cruz on Google Flights for the dates shown above (Nov 2026) — the fare I found is usually still available there.
- Compare the same dates on metasearch sites like Skyscanner or KAYAK to confirm you’re seeing the lowest price.
- Book directly with the airline when you can — it’s often the same price and makes changes or cancellations much easier.
Fares change constantly. If the price has moved, check back — I re-check this route daily.
Other Chicago to … flights
- Chicago to Sydney flights — US$1,322
- Chicago to Cairns flights — US$1,411
- Chicago to Melbourne flights — US$1,274
- Chicago to Sao Paulo flights — US$771
- Chicago to Gold Coast flights — US$1,453
- Chicago to Queenstown flights — US$1,530
- Chicago to Christchurch flights — US$1,464
- Chicago to Wellington flights — US$1,530
All flights to Santa Cruz · All flights from Chicago
Prices last checked: 2026-08-07, 10:08:40 p.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.