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Cheap flights from Port of Spain to Chicago from $275

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Port of Spain to Chicago departing on 2/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Port of Spain to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Port of Spain to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Port of Spain to Chicago.

Cheap last minute flights

Planning a quick getaway from Port of Spain to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Port of Spain to Chicago

Find recent round-trip train or bus tickets from Port of Spain to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
5:50 pm - 10:16 pmPOS-ORD
30h 26m2 stops
8:12 pm - 4:29 pmORD-POS
42h 17m2 stops
$335Frontier
Find Deal
dom., feb. 2 - vie., feb. 7
7:55 am - 5:42 pmPOS-ORD
10h 47m1 stop
10:10 am - 9:20 pmORD-POS
10h 10m1 stop
$561American Airlines
Find Deal
mar., may. 20 - mar., jun. 3
7:55 am - 9:37 pmPOS-ORD
14h 42m2 stops
7:30 am - 9:20 pmORD-POS
12h 50m2 stops
$566American Airlines
Find Deal
mar., may. 20 - mar., jun. 3
12:30 am - 12:10 amPOS-ORD
24h 40m1 stop
9:10 pm - 11:23 pmORD-POS
25h 13m1 stop
$666United Airlines
Find Deal
lun., may. 19 - mar., jun. 3
12:30 am - 9:25 amPOS-ORD
9h 55m1 stop
9:10 pm - 11:23 pmORD-POS
25h 13m1 stop
$667United Airlines
Find Deal
lun., may. 19 - mar., jun. 3
7:40 am - 11:58 pmPOS-ORD
18h 18m2 stops
1:44 pm - 4:30 pmORD-POS
24h 46m1 stop
sáb., ene. 4 - sáb., ene. 11
3:18 pm - 7:23 amPOS-ORD
17h 05m2 stops
8:25 pm - 2:03 pmORD-POS
16h 38m2 stops
$1,062American Airlines
Find Deal
jue., mar. 13 - vie., mar. 21
10:10 am - 8:37 amPOS-ORD
24h 27m2 stops
3:22 pm - 6:25 pmORD-POS
25h 03m2 stops
$1,074
Find Deal
sáb., ene. 4 - sáb., ene. 11
2:35 am - 8:00 amPOS-ORD
30h 25m2 stops
6:20 pm - 1:35 amORD-POS
54h 15m2 stops
$1,605Air Canada
Find Deal
lun., may. 19 - mar., jun. 3
2:35 am - 8:00 amPOS-ORD
30h 25m2 stops
6:20 pm - 1:35 amORD-POS
54h 15m2 stops
$1,670Air Canada
Find Deal
lun., may. 19 - mar., jun. 3
9:10 am - 4:56 pmPOS-ORD
33h 46m2 stops
lun., feb. 17
3:39 am - 1:11 pmPOS-ORD
10h 32m1 stop
$293Copa Airlines
Find Deal
sáb., mar. 15
1:30 am - 11:23 amPOS-ORD
11h 53m1 stop
$309United Airlines
Find Deal
dom., feb. 16
4:35 pm - 9:02 amPOS-ORD
18h 27m1 stop
$358American Airlines
Find Deal
lun., feb. 17
7:40 am - 8:44 pmPOS-ORD
15h 04m3 stops
lun., feb. 17
3:18 pm - 9:03 amPOS-ORD
18h 45m1 stop
$652American Airlines
Find Deal
dom., mar. 16
3:18 pm - 7:23 amPOS-ORD
17h 05m2 stops
$662American Airlines
Find Deal
dom., mar. 16
8:15 am - 7:46 amPOS-ORD
24h 31m3 stops
$1,383
Find Deal
dom., mar. 16
12:30 am - 6:50 pmPOS-ORD
19h 20m2 stops
$3,582United Airlines
Find Deal
sáb., mar. 15
2:20 am - 6:35 pmPOS-ORD
18h 15m2 stops
$4,514United Airlines
Find Deal
dom., feb. 16
1:30 am - 11:59 pmPOS-ORD
24h 29m1 stop
8:20 pm - 12:23 amORD-POS
26h 03m1 stop
$563United Airlines
Find Deal
dom., nov. 24 - mar., dic. 3
4:17 pm - 11:55 pmPOS-ORD
9h 38m1 stop
7:00 am - 10:48 pmORD-POS
13h 48m2 stops
$911American Airlines
Find Deal
lun., nov. 25 - mar., dic. 3
4:17 pm - 11:55 pmPOS-ORD
9h 38m1 stop
8:15 am - 10:48 pmORD-POS
12h 33m1 stop
$927American Airlines
Find Deal
lun., nov. 25 - mar., dic. 3
6:54 am - 7:17 pmPOS-ORD
14h 23m2 stops
7:00 am - 10:48 pmORD-POS
13h 48m2 stops
$1,047American Airlines
Find Deal
lun., nov. 25 - mar., dic. 3
7:55 am - 10:07 pmPOS-ORD
16h 12m2 stops
8:25 pm - 7:50 pmORD-POS
21h 25m3 stops
$1,537
Find Deal
lun., nov. 25 - mar., dic. 3

American Airlines flights from Port of Spain to Chicago

Our best American Airlines deals on Port of Spain to Chicago flight tickets
American Airlines
May 20
POS7:55 amPort of Spain Piarco Intl
10h 47m
1 stop
ORD5:42 pmChicago O'Hare Intl
Jun 3
ORD10:10 amChicago O'Hare Intl
10h 10m
1 stop
POS9:20 pmPort of Spain Piarco Intl
American Airlines
May 20
POS7:55 amPort of Spain Piarco Intl
14h 42m
2 stops
ORD9:37 pmChicago O'Hare Intl
Jun 3
ORD7:30 amChicago O'Hare Intl
12h 50m
2 stops
POS9:20 pmPort of Spain Piarco Intl
American Airlines
Nov 25
POS4:17 pmPort of Spain Piarco Intl
9h 38m
1 stop
ORD11:55 pmChicago O'Hare Intl
Dec 3
ORD7:00 amChicago O'Hare Intl
13h 48m
2 stops
POS10:48 pmPort of Spain Piarco Intl

United Airlines flights from Port of Spain to Chicago

Our best United Airlines deals on Port of Spain to Chicago flight tickets
United Airlines
Nov 24
POS1:30 amPort of Spain Piarco Intl
24h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
Dec 3
ORD8:20 pmChicago O'Hare Intl
26h 03m
1 stop
POS12:23 amPort of Spain Piarco Intl
United Airlines
May 19
POS12:30 amPort of Spain Piarco Intl
24h 40m
1 stop
ORD12:10 amChicago O'Hare Intl
Jun 3
ORD9:10 pmChicago O'Hare Intl
25h 13m
1 stop
POS11:23 pmPort of Spain Piarco Intl
United Airlines
May 19
POS12:30 amPort of Spain Piarco Intl
9h 55m
1 stop
ORD9:25 amChicago O'Hare Intl
Jun 3
ORD9:10 pmChicago O'Hare Intl
25h 13m
1 stop
POS11:23 pmPort of Spain Piarco Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Port of Spain to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $0. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Port of Spain to Chicago for around $1,058.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Port of Spain to Chicago during this time can be as low as $716. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $830.

When to book flights from Port of Spain to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Port of Spain to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Port of Spain to Chicago (POS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Port of Spain to Chicago

Best Price Found

$275

Fastest flight time

9h 41m

Direct flights

None

Airports in Chicago

1 airport
The best one-way flight to Chicago from Port of Spain in the past 72 hours is $275. The best round-trip flight deal from Port of Spain to Chicago found on momondo in the last 72 hours is $335.
The fastest flight from Port of Spain to Chicago takes 9h 41m
There are no direct flights from Port of Spain to Chicago. Popular non-direct route for this connection is Port of Spain Piarco Intl Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • How far is Port of Spain Piarco Intl to Chicago by plane?

    Port of Spain Piarco Intl and Chicago are 2671.5 mi apart from one another. A reasonable flight in good conditions will take 9h 41m.

  • When did momondo last update prices for flights from Port of Spain Piarco Intl Airport to Chicago?

    Prices for flights from Port of Spain Piarco Intl Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Port of Spain Piarco Intl Airport to Chicago?

  • How old do you have to be to fly from Port of Spain Piarco Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Port of Spain Piarco Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Port of Spain to Chicago?


Best airlines flying from Port of Spain to Chicago

Compare and see reviews for airlines that fly from Port of Spain to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $505Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
American AirlinesPriceFrom $556Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Port of Spain to Chicago?

Finding the right flight to Chicago from Port of Spain is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Port of Spain to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Port of Spain to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Port of Spain to Chicago?

momondo helps you find the best flight between Port of Spain and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Port of Spain to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Port of Spain to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago