$368 Find Cheap Flights from Trinidad and Tobago to Illinois

1 adult
1 adult, Economy

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 for flights to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

What is the cheapest month to fly from Trinidad and Tobago to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Trinidad and Tobago 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 Trinidad and Tobago to Illinois is June, when tickets cost $453 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $1,475 and $792 respectively.


Good to know

Low seasonOctober
High seasonDecember
Cheapest flight$368
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Port of Spain to Chicago

FAQs for booking flights from Trinidad and Tobago to Illinois

  • How does KAYAK find such low prices on flights from Trinidad and Tobago 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 Trinidad and Tobago to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Trinidad and Tobago to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Trinidad and Tobago 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 Trinidad and Tobago 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 Trinidad and Tobago 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 Trinidad and Tobago 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 Trinidad and Tobago to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $603. On the other hand, the most expensive day to fly is Wednesday, where round-trip prices are $717 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $716 on average. Morning departures are around 5% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $830.

Reviews of the top airlines flying from Trinidad and Tobago to Illinois

 
See real verified KAYAK customer reviews for airlines flying to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Trinidad and Tobago to Illinois. 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 Trinidad and Tobago 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 8858 reviews
7.0Entertainment
8.1Crew
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

Overall it was good. I missed my connection but I was put on another flight.

8.0 ExcellentJohanna, Jul 2025IAH - ORD
Read more United Airlines reviews

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Book cheap flights from Trinidad and Tobago to Illinois

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Illinois found on KAYAK in the last 72 hours.
9/9Tue
1 stop
25h 08mPOS-ORD
9/27Sat
1 stop
24h 16mORD-POS
$488
9/9Tue
1 stop
25h 08mPOS-ORD
9/22Mon
1 stop
13h 55mORD-POS
$499
9/12Fri
1 stop
25h 08mPOS-ORD
9/21Sun
1 stop
13h 55mORD-POS
$500
9/8Mon
2 stopsAir Canada
37h 30mPOS-ORD
9/24Wed
2 stopsAir Canada
54h 19mORD-POS
$565
9/5Fri
1 stopUnited Airlines
17h 40mPOS-ORD
9/23Tue
1 stopUnited Airlines
15h 23mORD-POS
$573
11/18Tue
1 stopUnited Airlines
10h 32mPOS-ORD
12/5Fri
1 stopUnited Airlines
9h 38mORD-POS
$574
8/30Sat
1 stopAmerican Airlines
15h 25mPOS-ORD
9/6Sat
2 stopsAmerican Airlines
18h 21mORD-POS
$578
11/21Fri
2 stopsAir Canada
18h 40mPOS-ORD
12/6Sat
2 stopsAir Canada
29h 10mORD-POS
$584
12/18Thu
1 stopAmerican Airlines
14h 26mPOS-ORD
1/29Thu
2 stopsAmerican Airlines
12h 58mORD-POS
$646
8/13Wed
1 stopCopa Airlines
10h 43mPOS-ORD
8/17Sun
1 stopCopa Airlines
16h 51mORD-POS
$726

Search by stops

Search by airline

Search by price

Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Illinois found on KAYAK in the last 72 hours.
8/3Sun
3 stops
35h 20mPOS-ORD
$368
8/3Sun
1 stop
24h 06mPOS-ORD
$392
8/3Sun
2 stops
22h 45mPOS-ORD
$408
8/2Sat
2 stops
18h 17mPOS-ORD
$759
8/2Sat
1 stopUnited Airlines
10h 51mPOS-ORD
$771
8/2Sat
3 stops
18h 31mPOS-ORD
$1,135

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.