Find cheap flights from Illinois to Trinidad and Tobago

Find cheap flights from Illinois to Trinidad and Tobago

Search hundreds of travel sites at once for deals on flights to Trinidad and Tobago. Bundle your flight + hotel and save!

Round-trip
Economy
Boston (BOS)
Trinidad and Tobago
Wed 8/4
Wed 8/11
Any month
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Good to know

Low season

MayBest time to beat the crowds with an average 10% drop in price.

High season

FebruaryMost popular time to fly with an average 23% increase in price.

Average price round-trip

$499(avg. price over the last 2 weeks)

Good deal round-trip

$274or less

Good deal one-way

$126or less

FAQs for booking flights from Illinois to Trinidad and Tobago

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Top 4 airlines serving from Illinois to Trinidad and Tobago

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,658 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "Tv dont work in a fly of 4hr 30 min"

Cons: "Flight information"

Pros: "Free wireless"
Cons: "I'm not in Charlotte"

Pros: "The friendly crew members"
Cons: "The snack items. After paying so much money for a flight to only be fed with a snack for a 4 and 1/2 hour flight is poor"

Pros: "Service was awesome, 100% recommended"

Pros: "Loved the roomy seats"
Cons: "Sound system was low quality. Hard to here the movie."

Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."

Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"

Cons: "The cabin crew was a little lacking and the captain did not mentioned that we had landed almost a full hour later than scheduled."

Pros: "Pilot’s smooth take off and landing."
Cons: "The weather haha."

Pros: "It was a great trip for the cost."
Cons: "Nothing."

Pros: "Free WiFi. Cute vids for Holloween"
Cons: "Nothing!"

Pros: "I liked that the pilot was able to make up some time because our flight was delayed over one hour in Chicago."
Cons: "The notification that the flight was boarding early. I enabled notifications and still did not receive notification that the plane was boarding."

Pros: "Nothing"
Cons: "Being delayed from 6am to 1:30pm"

Pros: "Flight was delayed 30 minutes at takeoff but landed when it was scheduled, so it was fine. Flight attendants didn’t make you stay in your seat, so you could use the lavatory. A fine, uneventful flight. Free WiFi. Snacks. Drinks. Fairly comfortable seats with decent legroom."
Cons: "Wish the seats in front of the emergency exit reclined."

Cons: "I had a very bad experience with Jet blue, they send me an email that the flight was still on time which was supposed to be at 11:am on September 21st , when we arived to the airport we found out that we were late for the flight so we missed our connecting flight, and we couldn’t get another flight to the destination, we paid for a full week and we won’t get there until Monday lm looking to get my money for All my losses, the Hotel in New York $254 the connecting flight and the coast of our resort, and all the aggravation the we got because of your scheduling, my name is Rola Barkho my address is 259 Wilson ave , Paramus nj 07652. Email address is rpperfectimage@aol. Com or my phone # is 201-913-9349 I will appreciate your concern. By the way it was our 28th years anniversary"

Pros: "Seat space for each passenger"

Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

Pros: "More leg room Affordable prices Snacks dunkin donut coffee Pleasant flight attendant Punctuality"
Cons: "Nothing"

Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"

Cons: "could not make it in time. Then we got on plane and pilot said it was an electrical problem on the flight but the generators were now up and at em again. Very hair raising ride for me - got in at 2:30 am with another hour to drive home - and I lost a LOT of confidence which I have always had in Jet Blue. I hope this is not the future we can expect with you"

Pros: "The crews were very friendly A lot of options from direct tv and other entertainment programs The seats were wide enough Free Wifi"
Cons: "The plane got 2 hours delayed The screen was too small There was no charger on the plane Food option was limited"

Pros: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."

Pros: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

Pros: "Seats were pretty comfortable with decent legroom."
Cons: "Plane was freezing cold, but a blanket had to be purchased."

Pros: "Loved the convenience of traveling one airline from Atlanta and my luggage booked through."
Cons: "No particulars"

Cons: "We arrived later for almost 2 hours"

Pros: "I dont usually fly, staff was friendly and helpful, made my experience less stressful."

Cons: "my flight was delayed for 2 hours and there was no compensation for it"

Pros: "There was nothing to like. The service and explanation for prolonged delays was very poor"
Cons: "Everything. This was the worst treatment ever"

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Cons: "No movies just Direct TV."

Pros: "Bring her own earphones as then u can listen to their varied entertainment channels. Gave free snacks & there was quite an assortment so I wasn’t stuck w pretzels again. Free soft drinks; nice flight attendants & smooth ride from Chicago to NY"

Pros: "No gate, waited 2 hours in plane"

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"

Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."

Pros: "Crew was happy and friendly"
Cons: "Can’t think of anything"

Pros: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."

Pros: "Entertainment on board"
Cons: "My flights was delayed"

Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."

Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"

Pros: "Nothing!!!!"
Cons: "I didn't like that I had to spend $300.00 USD on a hotel!!!"

Pros: "I liked the crew. Friendly and professional. I liked the room between seats even though I wasn't in even more space."
Cons: "Food offerings could be better."

Pros: "the plane was good!"
Cons: "the plane boarded late"

Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"

Pros: "Service and comfort"
Cons: "Food"

Pros: "the flights were on time"
Cons: "the plane was packed. the audio on the entertainment system did not work. the flight attendant gave me water and a juice, but handed them both at the same time and I spilled some juice to avoide the person next to me on this packed flight."

Cons: "Had an issue with my passport and the manager at the check in counter was rude and not helpful."

Pros: "Great crew; efficient, kind and accessible."
Cons: "Entertainment system. Tiny screens and no options."

Pros: "Good"
Cons: "Good service"

Pros: "The food"
Cons: "Everything ok"

Pros: "Change flight without notifying me"
Cons: "Change flight without notification"

Pros: "Every thing was excellent"

Pros: "excellent service"

Pros: "Everything"

Pros: "The seats were comfortable, they served a free snack and also a adult beverage"

Pros: "Everything. They try so hard to accommodate regardless of class."
Cons: "Planes are equipped with old entertainment screens. Not a big deal though as you bring your own entertainment now a days."

Pros: "Service was good"

Pros: "Everything was great!"

Pros: "Every time I fly or my son-in-law connect through there it is the wonderful. We've never had such painless connections ever!"
Cons: "Was surprised warm beverages weren't served. A coffee would have been nice."

Pros: "Good servoe"
Cons: "No WIFI connection movie selections"

Cons: "Uncomfortable seats. I ordered Kosher meals, but they did not have any available, so I pretty much watched everyone else eat while I couldn't."

Pros: "copa is punctual with the flights and offer a good service in the air."

Pros: "Food was tasty and served quickly ...staff was friendly and extremely polite"
Cons: "The usual with all planes when you fly economy ...cramped seats"

Pros: "Service was excellent"

Pros: "Es la Primera vez qué vuelo con Uds. Me gusto La amabilidad del personal. Sigan así no cambien."
Cons: "Uds deberían llamar primero a Los grupos finales, ejemplo 5 ó 6 para evitar incomodidades por el pasillo."

Pros: "The crew was great the food and service"
Cons: "For a 5 hour plus flight would have liked a more updated cabin with a charging station for electronic devices and possibly an entertainment center"

Pros: "Evrything fine!!!"
Cons: "No whell chair wait for me only this!!"

Pros: "Great crew from Chicago to Panama City. Accommodating and attentive."
Cons: "Ah, the usual airline stuff that we just have to live with."

Pros: "Drinks"
Cons: "No entertainment OR WIFI?!"

Pros: "The staff was extremely helpful and pleasant. It seems like everyone spoke English and Spanish. Free drinks. A fine flight."
Cons: "Not a thing."

Pros: "All. A lot better. Of. Any. USA are line"
Cons: "All"

Pros: "The crew was really nice"
Cons: "There weren’t good options on food, and even it’s a 5 hours flight there was not internet or screen on the chairs."

Pros: "They provide any of your requests is they have it"
Cons: "Everything was fine"

Pros: "Crew was courteous, and very polite."

Pros: "Food was ok"
Cons: "No WiFi, no outlets, no entertainment for international flights seems very outdated."

Pros: "Short flight and thankfully I slept a bit."
Cons: "The stewardesses just say in their area. Never offered extra coffee or drinks. No snacks. Food was pathetic."

Pros: "Friendly service, food and drink included, and free luggage. Seats had limited leg room, but otherwise comfortable. Would select this airline again!"

Pros: "Free food and Cocktails!! On time and quick boarding. My first flight with Copa Airlines, won't be my last!!"

Pros: "The food and service"
Cons: "Maybe more entertainment for a 5 hour flight"

Pros: "The crew and staff were wonderful and professional"

Pros: "Nothing. Even when it's the cheapest flight, th insignificant price difference vs. other airlines doesn't compensate the awful experience"
Cons: "The treatment of the crew was unrespectul. The food is extremely bad. The airplane and seats were uncomfortable."

Pros: "Duration of flight."
Cons: "Food"

Pros: "Service of crew excellent. On time and good arrival. Web check in let me pick my seat. And nice stewardesses"

Pros: "Service."
Cons: "nothing"

Pros: "Crew was great and friendly."
Cons: "No on board entertainment."

Pros: "Great service."

Pros: "Liked the dairy free options for the meal."
Cons: "Didn't have an individual tv to watch movies on, or cell phone charger. Given the price however, this was acceptable."

Pros: "nothing"
Cons: "custumer service"

Pros: "Planes are clean and crew is nice"
Cons: "Overall they are a poorly organized airline and there is almost no entertainment."

Pros: "plane was comfortable"
Cons: "Flight attendants weren't very polite."

Pros: "Comfortable leg room Friendly cabin crew"
Cons: "Very limited food options, International flights have poor entertainment options, Very old seats and covers gave a very dull impression"

Pros: "I love flying Copa! My friend and I had only a 40 minute layover on Tuesday morning from San Jose, CR to Panama City to Chicago. We were pretty worried about missing the flight in Panama City because that meant we missed our fight home. The crew was wonderful and changed our seats to the front of the plane so we wouldn't miss the flight. If he hadn't had done that, we 100% would have missed the flight .I will recommend Copa to everyone."

Pros: "Food and drinks."
Cons: "Bad entertainment selection and screen."

Pros: "Free novies"
Cons: "Food service and better social distancing"

Pros: "Seat room is limited, especially when you are in the middle seat."
Cons: "Seat space"

Pros: "Great price!"
Cons: "More food."

Cons: "Had to clean my seat before seating."

Cons: "The legroom is not sufficient for taller people"

Cons: "Unable to play entertainment on my compatible device."

Cons: "The terrible communication for delays and boarding."

Cons: "Feeling of being cramped"

Cons: "I will never, ever book with Kayak again"

Pros: "Busy but kind stewardesses"
Cons: "Please offer another snack option besides carboard flavored pretzels."

Cons: "Pushy crowd.."

Cons: "Kept the lights on for too long serving dinner. Forgot to serve the middle section beverages during breakfast."

Pros: "Nothing"
Cons: "Cancelled"

Pros: "Nothing"
Cons: "Incredibly uncomfortable. I even paid extra for more room. Meals were a joke"

Pros: "Great service"

Pros: "Amazing entertainment selection, comfortable."

Pros: "Almost empty in economy"
Cons: "I liked everything"

Cons: "For our delay with no information"

Pros: "Food was surprisingly good. Smooth ride could have been just good weather, but it was nice. We got in early!!!"
Cons: "Legroom was ok for me because I'm short. Others may have needed more."

Pros: "The airplale MD 80 are old"

Pros: "Excellent service. Loved the tv screens with the remote. Exclennt flignt"

Cons: "They were late because of bad scheduling and the gate agent was rude"

Cons: "I loved everything"

Pros: "was a pain checking extra baggage. No one seemed to know what to do.. Apart from that AA was good."

Pros: "Everything was great. Easy boarding great comfortable seating and friendly efficient stewardship"

Cons: "Boarding was a little chaotic. Could have been more organized."

Pros: "Everything was on time!"

Pros: "Extra blanket and pillow. Empty seat to sleep in. Fairly clean interior for the most part."

Pros: "All good! Nice staff. Easy travel."

Cons: "Three gate changes and 45 minute delay. Same happened two years ago"

Pros: "Free alcohol and good passenger friends and friendly service."
Cons: "No outlets for phones"

Pros: "All the movies"
Cons: "Legroom"

Cons: "Could not read paper when passenger in front reclined seat. No space between rows."

Pros: "Clean environment of the terminals and the speed of the shuttle."
Cons: "no comment."

Pros: "It took off on time and life was good."

Cons: "No complaints."

Pros: "Great service!"

Pros: "Everything"

Cons: "Requested for wheelchair assistance but none provided?!!"

Pros: "Timing and transit time was excellent"

Pros: "Everything."
Cons: "Nothing."

Pros: "Price space, time"
Cons: "Waiting.. but better to be early than late"

Cons: "Food was horribe and no dedicated tv per seat"

Pros: "Everything was pretty decent.. Best part was the price.. Boarding was good staff was good"
Cons: "Wasn't enough room.. kind of tight.. Couple more inches all around would have been perfect though"

Pros: "Ease of travel"

Pros: "All personnel where polite,helpful, and respectful. Greg to have wifi and power chargers."
Cons: "There was no real entertainment on the screens. No movies."

Pros: "On time."

Pros: "very good no problems.."
Cons: "all good thanks much"

Cons: "Always a problem with these guys"

Cons: "Delayed"

Pros: "Efficient"
Cons: "Free wifi"

Pros: "Everything"
Cons: "Perfect"

Pros: "Getting a meal and drink"

Pros: "One attendant did it all. And very well. Impressive."
Cons: "More snack options."

Pros: "Everything from ticketing to deplaning was smooth and professional."
Cons: "No problems at all."

Pros: "On time"

Pros: "Having about an hour and 20 minutes left me with enough time to explore the airport from one gate to the other without feeling terribly rushed."
Cons: "The ONLY thing negative that I can say is that the Chicago airport had no charging stations at my gate."

Cons: "No bags to go to overhead bin"

Pros: "Not much"
Cons: "The food not fit for human consumption"

Pros: "Quick boarding. Ontime departure."
Cons: "Very small servings of food."

Pros: "comfortable and on time"

Pros: "Happy people"

Pros: "Dr usus I"
Cons: "The keys"

Pros: "The seating was comfortable. On the Chicago keg I was seated in the middle and was not stuck with people who were too big for the seat. I noticed there was an overweight person in first class. Does United have strict policies on size?"
Cons: "Just the fourth seating group had trouble finding a place for my roller board carry on."

Pros: "boarding very easy"
Cons: "no drinks ir snacks offered"

Cons: "Very uncomfortable plane!"

Cons: "Lines"

Pros: "United payed for the room and 20 bucks for food."
Cons: "Late. Missed the connection to Gillette and had to stay overnight."

Pros: "We'll coordinated."

Cons: "See above comments."

Pros: "The service was good"

Pros: "Glad you didn't give priority to those with other designations like priority plus etc"

Cons: "Plane late leaving Chicago due to no pilot."

Pros: "Great"

Pros: "On time"
Cons: "Small plane"

Pros: "I got in my final destination"
Cons: "Everything"

Cons: "Long delay in chicago waiting for take off"

Cons: "More maintenance delays."

Cons: "Lost my luggage"

Pros: "Same as above"

Pros: "Everything was on time and went really smoothly."

Pros: "Every one was friendly. The plane was clean"

Cons: "They didn't have wifi"

Pros: "no complaints"

Pros: "Was never in Chicago."
Cons: "Was never in Chicago but my stuff was."

Pros: "Everything went well and was on time"

Pros: "Perfect, but I did upgrade to United's business plus."

Pros: "Aisle seat."
Cons: "They made my dad check his bag even though there was space."

Pros: "Worst flying experience ever"

Cons: "I was informed today that one of my checked bags was picked up by another customer who eventually realized it was not her bag. She brought it back to the airport and refused to turn over the bag until the airport compensated her. (How this happened I have no idea because I stood right by the entrance of the baggage claim and never saw the bag come out). The customer refused to return the bag until the police became involved at which point she agreed to write a note confirmed she did not steal anything. The bag then needs to be sent to me in 2 days and I'll have to verify myself that indeed nothing was taken from the bag. I'm very concerned how this individual came to be in possession of my bag considering, again, I stood right at the entrance of the baggage claim conveyor belt from the time it started to when it ended. As a result, this experience really made me feel frustrated and violated."

Pros: "on-time! Even a little early!"

Pros: "By bag was broken when I got to my final destination. It looked like they played football with it. I'm filing a claim with United Airlines"

Pros: "Please address the lax enforcement of one carry-on and one under-the-seat bag/passenger."
Cons: "Overhead compartments were full by the time I boarded so my bag was taken and tagged, as was several other passengers. I noticed upon arrival in Hartford that several passengers had 2 bags in the overhead compartment and their coats as well. If you have a policy of one carry-on and one under-the-seat/passenger, why isn't this enforced? It is not fair to the Group 4 and 5 passengers that there is no room in the overhead compartments and they are forced to relinquish their bags. Furthermore, this results in them having to go to the baggage claim area and wait for their carry-on. This added a half hour to my time and my ride had to circle the airport waiting for me to come out."

Pros: "Overall I arrived at my final destination in one piece. I'm satisfied :)"

Pros: ":("
Cons: ":("

Cons: "The airline checkin is terrible and time consuming!"

Cons: "Never made it because of stupid United"

Pros: "The pilot got us there safely. Good deal of turbulence."
Cons: "Stewardesses were rude to many. Chit chatted with each other whole way, ignored passengers. "Too turbulent" to serve us a beverage, which was okay. Except first class got full service. Wrong."

Pros: "I really loved the room on the ph"

Pros: "Smooth thru0"
Cons: "O"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Illinois to Trinidad and Tobago

Airlines flying from Illinois to Trinidad and Tobago have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Illinois to Trinidad and Tobago

Mandatory masks

Masks required on board, masks provided on flights from Illinois to Trinidad and Tobago

Social distancing seating

Middle seats unavailable to book on flights from Illinois to Trinidad and Tobago

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Illinois to Trinidad and Tobago

Book cheap flights from Illinois to Trinidad and Tobago

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