Cheap flights from Chicago (CHI) to Trinidad and Tobago from $216
Travelers have found it’s best to book a flight 61 days in advance to save up to 15% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 61 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Trinidad and Tobago 1-2 weeks in advance for as low as $672, or $828 for flights within the next 24 hours.
Flights from Chicago to Trinidad and Tobago lean towards being more expensive in February. Prices are generally better when you fly from Chicago to Trinidad and Tobago in January, with the cheapest ticket starting at $471.
When flying from Chicago to Trinidad and Tobago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Cheap flights from Chicago to Trinidad and Tobago in March, April 2023
The best prices found for CHI to Trinidad and Tobago flights for March, April
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 05mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
48h 05mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
13h 10mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
24h 05mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
19h 52mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
31h 04mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 05mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
16h 43mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
3 stops
29h 12mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
31h 04mMultiple Airlines
Chicago to Trinidad and Tobago 2023 flight deals
Cheap flights to Trinidad and Tobago from Chicago found for this year
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
9h 28mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
10h 37mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
25h 18mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
10h 37mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
25h 18mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
32h 15mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
25h 18mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
10h 37mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
25h 18mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
23h 22mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 35mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
10h 37mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 35mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
32h 15mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
25h 18mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
25h 00mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 35mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
25h 00mUnited Airlines
Cheap American Airlines flights from Chicago to Trinidad and Tobago
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
41h 53mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
18h 29mAmerican Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
41h 29mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
18h 15mAmerican Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
18h 53mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
20h 11mAmerican Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
41h 53mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
18h 15mAmerican Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
16h 18mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
17h 29mAmerican Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
18h 53mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
9h 50mAmerican Airlines
Cheap Copa Airlines flights from Chicago to Trinidad and Tobago
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
15h 22mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
16h 14mCopa Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
15h 22mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
15h 31mCopa Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
14h 50mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
15h 57mCopa Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
15h 06mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
15h 31mCopa Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
12h 54mPort of Spain Piarco Intl
Chicago O'Hare Intl
1 stop
10h 24mCopa Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
13h 32mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
15h 31mCopa Airlines
Last minute flights from Chicago to Trinidad and Tobago
Late deals on return flights to Trinidad and Tobago from Chicago, departing today and this week
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 05mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
48h 05mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
13h 10mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
24h 05mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
19h 52mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
31h 04mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
13h 05mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
16h 43mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
3 stops
29h 12mPort of Spain Piarco Intl
Chicago O'Hare Intl
2 stops
31h 04mMultiple Airlines
One-way flights to Trinidad and Tobago from Chicago
The cheapest one-way flights from Chicago to Trinidad and Tobago
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
16h 23mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
26h 45mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
30h 33mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
25h 18mUnited Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
27h 33mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
3 stops
26h 30mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
3 stops
26h 30mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
2 stops
19h 03mMultiple Airlines
Chicago O'Hare Intl
Port of Spain Piarco Intl
1 stop
16h 18mAmerican Airlines
Find flights from Chicago to Trinidad and Tobago within your budget
Use the slider to find flights from Chicago to Trinidad and Tobago that fit your budget.
Fly from
Fly to
Budget
$484 - $766
Route
Depart
Return
Price
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-06-07
1 stop9h 28m
Port of Spain Piarco Intl
2023-06-21
1 stop10h 37m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-06-04
1 stop25h 18m
Port of Spain Piarco Intl
2023-06-19
1 stop10h 37m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-06-04
1 stop25h 18m
Port of Spain Piarco Intl
2023-06-22
1 stop32h 15m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-06-10
1 stop25h 18m
Port of Spain Piarco Intl
2023-06-21
1 stop10h 37m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-06-04
1 stop25h 18m
Port of Spain Piarco Intl
2023-06-23
1 stop23h 22m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-05-15
2 stops41h 53m
Port of Spain Piarco Intl
2023-05-20
2 stops18h 29m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-05-05
2 stops41h 29m
Port of Spain Piarco Intl
2023-05-12
1 stop18h 15m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-05-15
1 stop15h 22m
Port of Spain Piarco Intl
2023-05-19
2 stops16h 14m
Chicago O'Hare IntlPort of Spain Piarco Intl
ORD - POS
ORDPOS
Chicago O'Hare Intl
2023-06-05
1 stop9h 25m
Port of Spain Piarco Intl
2023-06-18
1 stop21h 00m
Reviews of Airlines Servicing Trinidad and Tobago
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
I always buy through Kayak. I seem to get the best deals, and I always fly United. It seems to work really well with me. No comp,aints. Thank you.
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
I always buy through Kayak. I seem to get the best deals, and I always fly United. It seems to work really well with me. No comp,aints. Thank you.
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
I always buy through Kayak. I seem to get the best deals, and I always fly United. It seems to work really well with me. No comp,aints. Thank you.
Entertainment
Overall
Boarding
Food
Comfort
Crew
Reviews
I always buy through Kayak. I seem to get the best deals, and I always fly United. It seems to work really well with me. No comp,aints. Thank you.
Related info for your journey
Useful info, stats and facts about Chicago to Trinidad and Tobago flights.
Some of our airline partners flying from Chicago to Trinidad and Tobago have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and Copa Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.
Yes, there are multiple flights from Chicago to Trinidad and Tobago for under $500. The cheapest flight booked recently is on United Airlines for just $484, but on average you can expect to pay $610.
There are currently 5+ open flights from Chicago to Trinidad and Tobago within the next 7 days for less than $1,200.
Before booking your flight from Chicago to Trinidad and Tobago check out the most popular airlines for this route: American Airlines, Copa Airlines or United Airlines.
On average you can expect to pay $949 for a flight from Chicago to Trinidad and Tobago. The cheapest flight overall is $586 while the most popular route, (Chicago O'Hare Intl - Port of Spain Piarco Intl) is currently priced at $524.
These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport flight would often be abbreviated as a ORD to POS flight. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.