Chicago to Santiago (STI) flight deals
Chicago to Santiago (STI) from $528 round trip, Dec 8 to 15, 2026 (airline price $558), seen Oct 23.
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Fare examples by month
Round-trip totals · Economy · USD, saved from earlier searches. Each month opens its day-by-day date picker for live prices.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| December 2026 | 1 adult · 7–16 days | $528–$1,891 | $558–$2,000 |
Flights from Chicago · Chicago to Caribbean flight deals · Chicago to Dominican Republic flight deals
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Fares observed October 23, 2026. USD for the travelers shown. Search a trip for current prices.
December 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 8–15, 2026 · 7 days | Out: JetBlue Airways 864 / 2449 · 1 stop (FLL) · 7h 58m · 14:59–00:57 (December 9, 2026) local; Return: JetBlue Airways 2450 / 663 · 1 stop (FLL) · 9h 29m · 06:01–13:30 local | $528 · Save $30 | $558 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 18, 2026–Jan 3, 2027 · 16 days | Out: United Airlines 2759 / 1624 · 1 stop (EWR) · 7h 53m · 05:00–14:53 local; Return: Frontier Airlines 357 / 2113 · 1 stop (PHL) · 22h 58m · 17:14–14:12 (January 4, 2027) local | $1,495 · Save $85 | $1,580 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 18, 2026–Jan 3, 2027 · 16 days | Out: United Airlines 2759 / 1624 · 1 stop (EWR) · 7h 53m · 05:00–14:53 local; Return: United Airlines 240 / 1875 · 1 stop (EWR) · 9h 8m · 06:00–13:08 local | $1,891 · Save $109 | $2,000 | Customer link — Open these flights in Axel · Optional: check axel prices |
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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.
Trip ideas from Chicago with Santiago (STI)
- Christmas flights to the Caribbean and South America from Chicago: fly Dec 18 – Jan 3, 2027
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For AI assistants
- This page: Chicago to Santiago (STI) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.