$441 Find Cheap Flights from Port of Spain to Illinois - Compare and Save

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 7/21. 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

Mon, Aug 31 - Mon, Sep 7
Air Canada Logo
1:25 am - 4:57 pm
POS
-
ORD
16h 32m
1 stop
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
$605Air Canada
Fri, Jul 10 - Sat, Aug 29
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Air Canada Logo
6:21 pm - 12:15 am
ORD
-
POS
28h 54m
2 stops
$630Air Canada
Wed, Jul 1 - Sun, Jul 5
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
$632Air Canada
Wed, Jul 8 - Sun, Aug 30
Air Canada Logo
1:25 am - 11:20 am
POS
-
ORD
34h 55m
2 stops
Air Canada Logo
6:21 pm - 12:15 am
ORD
-
POS
28h 54m
2 stops
$633Air Canada
Wed, Jul 1 - Sun, Jul 5
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$635Air Canada
Sun, Nov 22 - Tue, Dec 8
United Airlines Logo
1:30 am - 9:42 am
POS
-
STL
10h 12m
1 stop
United Airlines Logo
6:15 am - 12:23 am
STL
-
POS
16h 08m
1 stop
$692United Airlines
Sun, Nov 22 - Tue, Dec 8
United Airlines Logo
1:30 am - 2:18 pm
POS
-
STL
14h 48m
2 stops
United Airlines Logo
6:40 am - 12:23 am
STL
-
POS
15h 43m
2 stops
$694United Airlines
Fri, Nov 20 - Tue, Dec 8
United Airlines Logo
1:30 am - 9:42 am
POS
-
STL
10h 12m
1 stop
United Airlines Logo
11:00 am - 12:23 am
STL
-
POS
11h 23m
1 stop
$715United Airlines
Fri, Nov 20 - Tue, Dec 8
United Airlines Logo
1:30 am - 2:18 pm
POS
-
STL
14h 48m
2 stops
United Airlines Logo
6:15 am - 12:23 am
STL
-
POS
16h 08m
1 stop
$717United Airlines
Sun, Nov 22 - Tue, Dec 8
Multiple Airlines Logo
2:20 am - 12:34 am
POS
-
STL
24h 14m
3 stops
Multiple Airlines Logo
4:15 pm - 7:40 pm
STL
-
POS
25h 25m
2 stops
$1,088Multiple 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.

What is the cheapest month to fly from Port of Spain to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Port of Spain to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Port of Spain to Illinois is April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are August and May, when the average cost of round-trip tickets is $792 and $691 respectively.

Good to know

Cheapest flight$441
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 airlines flying 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.
7.4
United AirlinesOverall score based on 9860 reviews
6.7Food
8.1Crew
7.7Boarding
7.3Comfort
7.1Entertainment
Airline reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

10.0 ExcellentJoanne, Jun 2026
DEN - ORD
Read more United Airlines reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

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

Information on your arrival and departure airports