Chicago to Santa Cruz flights (ORD → VVI)
Looking for Chicago to Santa Cruz flights? Cheapest round-trip I’ve found: US$621 on COPA, 1 stop(s), departing 2027-02-28. That’s US$80 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: Average price — cheaper than 40% of prices I’ve seen on this route.
Best months to fly Chicago to Santa Cruz
| Month | Cheapest seen |
|---|---|
| November | US$568 |
| February | US$588 |
| September | US$600 |
| December | US$601 |
| October | US$630 |
| January | US$661 |
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 (Feb 2027) — 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 Adelaide flights — US$1,386
- Chicago to Christchurch flights — US$1,458
- Chicago to Brasilia flights — US$643
- Chicago to Budapest flights — US$637
- Chicago to Sydney flights — US$1,346
- Chicago to Brisbane flights — US$1,322
- Chicago to Istanbul flights — US$797
- Chicago to Sao Paulo flights — US$773
All flights to Santa Cruz · All flights from Chicago
Prices last checked: 2026-09-24, 10:12:26 p.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.