Cheap flights from Port of Spain to Chicago

Flights overview

Useful information for finding cheap flights from Port of Spain to Chicago and booking your next trip
Cheapest one-way flight $357
Air Canada 1 stop 17 hr Thu, Jul 2
The cheapest one-way flight from Port of Spain to Chicago is currently $357
Fastest flight 9 hr 17 min The fastest flight with stops from Port of Spain to Chicago takes 9 hr 17 min
Nonstop flights None There are no direct flights on this route.

Popular airlines from Port of Spain to Chicago

  • American
    Typical price: $570–1,050
    76 weekly connecting flights
    POS - ORD Every day
  • United
    Typical price: $560–940
    60 weekly connecting flights
    POS - ORD Every day
  • JetBlue
    Typical price: $710–1,250
    21 weekly connecting flights
    POS - ORD Every day
  • COPA
    Typical price: $580–1,400
    18 weekly connecting flights
    POS - ORD Every day
  • Air Canada
    Typical price: $470–1,450
    12 weekly connecting flights
    POS - ORD Every Mon, Tue, Sat

Popular airports near Port of Spain

  • 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

Popular airports near Chicago

  • 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

Frequently asked questions about flying from Port of Spain to Chicago

The cheapest one-way flight was with Air Canada from $357.

Some of the cheapest round-trip deals we found with different airlines:
    The cheapest one-way flight starts at $357 and departs on Thu, Jul 2.
    9 hr 17 min is the shortest flight time from Port of Spain to Chicago.
    Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
    It's easy to use Google Flights to find the cheapest days to fly from Port of Spain to Chicago.
    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 Port of Spain to Chicago 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 Port of Spain to Chicago.

    In terms of flights, American is the most popular. American offers 76 connecting flights per week. American flies from Piarco International Airport (POS) to Chicago O'Hare International Airport (ORD) .

    Other popular airlines flying from Port of Spain to Chicago are:
    • United offers 60 connecting flights per week. United flies from Piarco International Airport (POS) to Chicago O'Hare International Airport (ORD) .
    • JetBlue offers 21 connecting flights per week. JetBlue flies from Piarco International Airport (POS) to Chicago O'Hare International Airport (ORD) .
    • COPA offers 18 connecting flights per week. COPA flies from Piarco International Airport (POS) to Chicago O'Hare International Airport (ORD) .
    • Air Canada offers 12 connecting flights per week. Air Canada flies from Piarco International Airport (POS) to Chicago O'Hare International Airport (ORD) .
    The number of connecting flights refers to distinct flights with at least one stop between Port of Spain and Chicago.
    The cheapest one-way flight was with Air Canada from $357.

    Some of the cheapest round-trip deals we found with different airlines:
      No airline flies direct from Port of Spain to Chicago.
      • There are 76 American connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 60 United connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 21 JetBlue connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 18 COPA connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 12 Air Canada connecting flights from Port of Spain to Chicago per week. Flights are available on Monday, Tuesday and Saturday.
      Use the Stops filter while searching for flights, to see only nonstop options in your results.
      The cheapest last-minute deal between Port of Spain and Chicago at price $633 is offered by Air Canada from Sat, May 9 to Sun, May 10.
      No airline flies direct from Port of Spain to Chicago.
      • There are 76 American connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 60 United connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 21 JetBlue connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 18 COPA connecting flights from Port of Spain to Chicago per week. Flights are available every day.
      • There are 12 Air Canada connecting flights from Port of Spain to Chicago per week. Flights are available on Monday, Tuesday and Saturday.
      Use the Stops filter while searching for flights, to see only nonstop options in your results.
      There are no direct flights from Port of Spain to Chicago.
      It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Port of Spain to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
      To book business class trips from Port of Spain to Chicago, 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.
      The best last-minute getaway deal for the next weekend between Port of Spain and Chicago starts at $633 from Sat, May 9 to Sun, May 10 with Air Canada.
      The cheapest last-minute deal between Port of Spain and Chicago at price $633 is offered by Air Canada from Sat, May 9 to Sun, May 10.
      To find last-minute flight deals from Port of Spain to Chicago, 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.

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      Popular trips from Port of Spain

      1. New York
        $364
        Jun 26 — Jul 9
        Nonstop 5 hr 24 min United
      2. London
        $861
        Jun 25 — Jul 9
        Nonstop 8 hr 40 min British Airways
      3. Paris
        $1,063
        Aug 24 — Sep 9
        2 stops 20 hr 45 min Air France, Caribbean Airlines, Virgin Atlantic
      4. Singapore
        May 3 — May 16

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