$282 Find Cheap Flights from Port of Spain to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Port of Spain to Illinois departing on 4/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Illinois, as well as popular online travel agencies
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Flight Deals

Book Cheap Port of Spain to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Port of Spain to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Port of Spain to Illinois

Tue, Mar 10 - Wed, Mar 18
Air Canada Logo
1:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
$478Air Canada
Wed, May 6 - Sun, May 10
Copa Airlines Logo
2:22 pm - 1:15 am
POS
-
ORD
11h 53m
1 stop
Copa Airlines Logo
3:21 pm - 1:46 am
ORD
-
POS
9h 25m
1 stop
$574Copa Airlines
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
9:10 am - 4:55 pm
POS
-
ORD
32h 45m
3 stops
Multiple Airlines Logo
3:55 pm - 12:20 am
ORD
-
POS
31h 25m
1 stop
$581Multiple Airlines
Tue, Mar 10 - Wed, Mar 18
Multiple Airlines Logo
1:20 am - 9:10 am
POS
-
ORD
32h 50m
3 stops
Multiple Airlines Logo
6:01 pm - 12:20 am
ORD
-
POS
29h 19m
2 stops
$601Multiple Airlines
Tue, Mar 10 - Wed, Mar 18
Multiple Airlines Logo
1:20 am - 9:10 am
POS
-
ORD
32h 50m
3 stops
Multiple Airlines Logo
6:01 pm - 12:20 am
ORD
-
POS
29h 19m
3 stops
$605Multiple Airlines
Wed, May 6 - Sun, May 10
American Airlines Logo
3:47 pm - 8:47 am
POS
-
ORD
18h 00m
2 stops
American Airlines Logo
5:00 am - 2:32 pm
ORD
-
POS
8h 32m
1 stop
$663American Airlines
Booking Insights

KAYAK's insights & trends for Port of Spain to Illinois flights

Get data-powered insights and trends into flights from Port of Spain to Illinois to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Port of Spain to Illinois?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Port of Spain to Illinois were found on Air Canada ($478) and Copa Airlines ($574).

Good to know

Cheapest flight$282
Flight from Port of Spain to Chicago

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Port of Spain to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Port of Spain to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Port of Spain to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Port of Spain to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Port of Spain to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Port of Spain to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Port of Spain to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Port of Spain to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Port of Spain to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Port of Spain to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Port of Spain to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
Copa AirlinesOverall score based on 1558 reviews
8.1Crew
7.8Boarding
6.8Entertainment
7.4Comfort
6.8Food
Airline reviews

A lot things happened in this trip.The fly should be less stress.

6.0 GoodIrma, Jan 2026
PTY - MIA
Read more Copa Airlines reviews

A lot things happened in this trip.The fly should be less stress.

Some of the Air hostesses are not that friendly. Need improvement

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

Great experience with a crew always thinking in the passenger

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Everything you need to know for your flight from Port of Spain to Illinois

Information on your arrival and departure airports