Cheap Flights from Port of Spain to Chicago
No deal from Port of Spain to Chicago has cleared our price bar yet. What we have seen on the route is below.
Across 3 months of observations from Port of Spain to Chicago, the lowest round-trip fare we recorded was $499, in August. The typical fare was $656. August was the cheapest month we saw and October the dearest.
The most recent price we saw on this route was $771 on United, seen Oct 17. It is an unverified observation and may have changed.
See every deal <a href="/from/port-of-spain">from Port of Spain</a>, <a href="/to/chicago">to Chicago</a>, or the return direction <a href="/from/chicago/to/port-of-spain">Chicago to Port of Spain</a>.
Latest price we saw: Port of Spain to Chicago
The most recent round-trip fare our sweep found on this route. It is not verified and may have changed since the date shown.
| From | Price | Per mile | Travel dates | Airline | Seen | Check price |
|---|---|---|---|---|---|---|
| Port of Spain (POS) to Chicago (ORD) | $771 | 14.3¢ | Nov 6 – Nov 12 | United | Oct 17 | Check price |
Price history: Port of Spain to Chicago
What we observed by month, from our signals database. Unverified observations, not bookable prices.
| Month | Low | Typical | Sightings |
|---|---|---|---|
| Oct 2026 | $636 | $700 | 7 |
| Sep 2026 | $588 | $655 | 18 |
| Aug 2026 | $499 | $613 | 15 |
Frequently asked questions
How many flight deals from Port of Spain to Chicago are on Sparkflights right now?
There are 0 verified deals from Port of Spain to Chicago on the board right now. The list refreshes hourly.
What is the lowest price ever seen from Port of Spain to Chicago?
The lowest fare we've recorded from Port of Spain to Chicago is $499, based on 40 price observations over 3 months.
How much does a flight from Port of Spain to Chicago cost?
The typical round-trip fare we observed from Port of Spain to Chicago is $656, against a recorded low of $499. These are observations, not quotes.
When is the cheapest month to fly Port of Spain to Chicago?
August was the cheapest month we observed from Port of Spain to Chicago and October the dearest, over 3 months of data.
What is the current price from Port of Spain to Chicago?
The most recent fare our sweep saw from Port of Spain to Chicago is $771, on Oct 17. It is an unverified observation rather than a verified deal, so check it before booking.