Cheap flights from Chicago to Port of Spain
Flights overview
Prices shown are for one adult in Economy class flights from Zürich to New York. This includes the cheapest Business class options where available.
Prices reflect the lowest available in the next three months, though they are subject to change and availability.
Last-minute deals apply to the cheapest weekend trips available in the next seven days, with weekend trips being flights departing between Thursday and Saturday and returning on Sunday or Monday.
Flight duration shown is based on nonstop flights or those with the fewest stops available.
Prices reflect the lowest available in the next three months, though they are subject to change and availability.
Last-minute deals apply to the cheapest weekend trips available in the next seven days, with weekend trips being flights departing between Thursday and Saturday and returning on Sunday or Monday.
Flight duration shown is based on nonstop flights or those with the fewest stops available.
Useful information for finding cheap flights from Chicago to Port of Spain and booking your next trip
| Cheapest round-trip flights | $576 |
Air Canada
1 stop
14 hr
Sun, May 3 — Sat, May 9
|
The cheapest round-trip flight from Chicago to Port of Spain is currently $576 | |
|---|---|---|---|---|
| Cheapest one-way flight | $249 |
Air Canada
1 stop
30 hr
Thu, Jun 4
|
The cheapest one-way flight from Chicago to Port of Spain is currently $249 | |
| Last-minute weekend getaway | $576 |
Air Canada
1 stop
32 hr
Thu, May 7 — Mon, May 11
|
The cheapest last-minute weekend getaway from Chicago to Port of Spain is currently $576 | |
| Cheapest business class flights | $922 |
United
1 stop
18 hr
Mon, Jul 13 — Wed, Jul 22
|
The cheapest business class round-trip flight from Chicago to Port of Spain is currently $922 | |
| Fastest flight | 8 hr 11 min | The fastest flight with stops from Chicago to Port of Spain takes 8 hr 11 min |
|---|---|---|
| Nonstop flights | None | There are no direct flights on this route. |
When is the cheapest time to fly?
Typical prices for the least expensive flights for 1-week trips from Chicago to Port of Spain per month. Insights are based on fares observed in the last 12 months. Current prices may differ.
The cheapest month to fly from Chicago to Port of Spain is typically April. The most expensive month to fly is typically August.
| April Cheapest
|
Typical prices: $380–630 |
|---|---|
| August Most expensive
|
Typical prices: $540–630 |
Popular airlines from Chicago to Port of Spain
Popularity is based on the number of weekly nonstop and connecting flights the airline operates. Connecting flights do not include interline routes.
Flight suggestions are based on an airline's cheapest round-trip fares from Chicago to Port of Spain in the next 3 months. Prices include required taxes + fees for one adult. Optional charges and bag fees may apply.
Typical prices are based on fares observed in the past year for one-week round trips with the same origin, destination, and airline.
- Americanfrom $662Typical price: $540–910143 weekly connecting flightsORD - POS Every day
- Unitedfrom $630Typical price: $540–83035 weekly connecting flightsORD - POS Every day
- JetBluefrom $626Typical price: $650–1,10021 weekly connecting flightsORD - POS Every day
- COPAfrom $618Typical price: $540–1,15021 weekly connecting flightsORD - POS Every day
- Air Canadafrom $546Typical price: $430–1,25018 weekly connecting flightsORD - POS Every Mon, Thu, Fri, Sat, Sun
Popular airports near Chicago
Distance and driving time are relative to the city center. Airports are listed based on distance from Chicago center and popularity with travelers.
- Chicago O'Hare International Airport (ORD)Chicago United States 26 min 16 mi
- Chicago Midway International Airport (MDW)Chicago United States 25 min 9 mi
- Milwaukee Mitchell International Airport (MKE)Milwaukee United States 1 hr 23 min 75 mi
- Indianapolis International Airport (IND)Indianapolis United States 2 hr 58 min 165 mi
Popular airports near Port of Spain
Distance and driving time are relative to the city center. Airports are listed based on distance from Port of Spain center and popularity with travelers.
- Piarco International Airport (POS)Port of Spain Trinidad & Tobago 29 min 12 mi
- ANR Robinson International Airport (TAB)Tobago Trinidad & Tobago 2 hr 59 min 57 mi
Frequently asked questions about flying from Chicago to Port of Spain
The cheapest flights from Chicago to Port of Spain are usually in April. Typical ticket prices in April range from $380 to $630.
The cheapest round-trip flight from Chicago to Port of Spain recently found on Google Flights was with Air Canada from $576. The cheapest one-way flight was with Air Canada from $249.
Some of the cheapest round-trip deals we found with different airlines:
Some of the cheapest round-trip deals we found with different airlines:
- The cheapest American flight from Chicago to Port of Spain is $662, flying from Jul 9 to Jul 15.
- The cheapest United flight from Chicago to Port of Spain is $630, flying from Jun 18 to Jun 24.
- The cheapest JetBlue flight from Chicago to Port of Spain is $626, flying from Jun 13 to Jun 19.
- The cheapest COPA flight from Chicago to Port of Spain is $618, flying from Jul 16 to Jul 22.
- The cheapest Air Canada flight from Chicago to Port of Spain is $546, flying from May 28 to Jun 6.
The cheapest round-trip flight from Chicago to Port of Spain starts at $576 from Sun, May 3 to Sat, May 9. The cheapest one-way flight starts at $249 and departs on Thu, Jun 4.
8 hr 11 min is the shortest flight time from Chicago to Port of Spain.
Port of Spain has a tropical climate with warm temperatures year-round. Mar–Apr are usually the driest months. The Trinidad and Tobago Carnival (Feb/Mar) attracts visitors with colorful street parades, steel drum orchestras, cultural shows and large outdoor parties known as “fetes.”
It's easy to use Google Flights to find the cheapest days to fly from Chicago to Port of Spain.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.
You can also turn on price tracking to get alerts if the price changes for a route or flight.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.
You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Chicago to Port of Spain really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Port of Spain.
In terms of flights, American is the most popular. American offers 143 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Piarco International Airport (POS) .
Other popular airlines flying from Chicago to Port of Spain are:
In terms of flights, American is the most popular. American offers 143 connecting flights per week. American flies from Chicago O'Hare International Airport (ORD) to Piarco International Airport (POS) .
Other popular airlines flying from Chicago to Port of Spain are:
- United offers 35 connecting flights per week. United flies from Chicago O'Hare International Airport (ORD) to Piarco International Airport (POS) .
- JetBlue offers 21 connecting flights per week. JetBlue flies from Chicago O'Hare International Airport (ORD) to Piarco International Airport (POS) .
- COPA offers 21 connecting flights per week. COPA flies from Chicago O'Hare International Airport (ORD) to Piarco International Airport (POS) .
- Air Canada offers 18 connecting flights per week. Air Canada flies from Chicago O'Hare International Airport (ORD) to Piarco International Airport (POS) .
The cheapest round-trip flight from Chicago to Port of Spain recently found on Google Flights was with Air Canada from $576. The cheapest one-way flight was with Air Canada from $249.
Some of the cheapest round-trip deals we found with different airlines:
Some of the cheapest round-trip deals we found with different airlines:
- The cheapest American flight from Chicago to Port of Spain is $662, flying from Jul 9 to Jul 15.
- The cheapest United flight from Chicago to Port of Spain is $630, flying from Jun 18 to Jun 24.
- The cheapest JetBlue flight from Chicago to Port of Spain is $626, flying from Jun 13 to Jun 19.
- The cheapest COPA flight from Chicago to Port of Spain is $618, flying from Jul 16 to Jul 22.
- The cheapest Air Canada flight from Chicago to Port of Spain is $546, flying from May 28 to Jun 6.
No airline flies direct from Chicago to Port of Spain.
- There are 143 American connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 35 United connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 21 JetBlue connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 21 COPA connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 18 Air Canada connecting flights from Chicago to Port of Spain per week. Flights are available on Monday, Thursday, Friday, Saturday and Sunday.
The cheapest last-minute deal between Chicago and Port of Spain at price $576 is offered by Air Canada from Thu, May 7 to Mon, May 11.
No airline flies direct from Chicago to Port of Spain.
- There are 143 American connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 35 United connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 21 JetBlue connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 21 COPA connecting flights from Chicago to Port of Spain per week. Flights are available every day.
- There are 18 Air Canada connecting flights from Chicago to Port of Spain per week. Flights are available on Monday, Thursday, Friday, Saturday and Sunday.
There are no direct flights from Chicago to Port of Spain.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Port of Spain, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Chicago and Port of Spain start at $922 from Mon, Jul 13 to Wed, Jul 22 with United.
The cheapest economy class round-trip flights between Chicago and Port of Spain start at $576 from Sun, May 3 to Sat, May 9.
To book business class trips from Chicago to Port of Spain, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.
You can also adjust the trip type to view one-way fares.
You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Chicago and Port of Spain starts at $576 from Thu, May 7 to Mon, May 11 with Air Canada.
The cheapest last-minute deal between Chicago and Port of Spain at price $576 is offered by Air Canada from Thu, May 7 to Mon, May 11.
To find last-minute flight deals from Chicago to Port of Spain, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.
You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.
You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.
Search more flights
Popular trips from Chicago
These suggestions are based on the cheapest fares to popular destinations in the next six months.
Prices include required taxes + fees for 1 adult. Optional charges and bag fees may apply.
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Miami$100Aug 6 — Aug 12Nonstop 3 hr 17 min Frontier
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Denver$158May 28 — Jun 3Nonstop 3 hr 7 min Frontier
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