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Cheap flights from Trinidad and Tobago to Chicago from $471

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Trinidad and Tobago to Chicago departing on 11/25. 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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0 bags

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Find the cheapest flights from Trinidad and Tobago to Chicago

Recent round-trip flight deals from Trinidad and Tobago to Chicago

Enter your travel dates to find the best prices.
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
$471Air Canada
Find Deal
mar., nov. 25 - lun., dic. 1
Air Canada Logo
2:15 am - 7:30 pmPOS-ORD
19h 15m1 stop
Air Canada Logo
3:55 pm - 1:10 amORD-POS
31h 15m1 stop
$483Air Canada
Find Deal
jue., nov. 13 - mié., nov. 26
Copa Airlines Logo
2:26 pm - 12:05 amPOS-ORD
11h 39m1 stop
Copa Airlines Logo
6:56 am - 1:48 amORD-POS
16h 52m1 stop
$562Copa Airlines
Find Deal
vie., nov. 14 - mié., nov. 26
United Airlines Logo
1:30 am - 10:58 amPOS-ORD
11h 28m1 stop
United Airlines Logo
5:49 am - 12:23 amORD-POS
16h 34m1 stop
$572United Airlines
Find Deal
sáb., dic. 20 - jue., ene. 1
United Airlines Logo
1:30 am - 10:56 amPOS-ORD
11h 26m1 stop
United Airlines Logo
10:36 am - 12:23 amORD-POS
11h 47m1 stop
$574United Airlines
Find Deal
sáb., nov. 22 - dom., nov. 30
American Airlines Logo
7:19 am - 6:17 pmPOS-ORD
12h 58m1 stop
American Airlines Logo
12:52 am - 3:30 pmORD-POS
12h 38m2 stops
$579American Airlines
Find Deal
mié., nov. 26 - dom., nov. 30
American Airlines Logo
4:30 pm - 9:05 amPOS-ORD
18h 35m1 stop
American Airlines Logo
7:17 pm - 3:30 pmORD-POS
18h 13m1 stop
$622American Airlines
Find Deal
dom., nov. 23 - dom., nov. 30
Multiple Airlines Logo
10:10 am - 6:39 pmPOS-ORD
10h 29m1 stop
Multiple Airlines Logo
5:45 am - 8:20 pmORD-POS
12h 35m2 stops
$649Multiple Airlines
Find Deal
sáb., dic. 20 - mié., dic. 31
Copa Airlines Logo
2:16 pm - 12:31 pmPOS-ORD
24h 15m1 stop
Copa Airlines Logo
7:34 am - 1:15 pmORD-POS
27h 41m1 stop
$653Copa Airlines
Find Deal
vie., feb. 27 - mar., mar. 3
Multiple Airlines Logo
10:10 am - 6:39 pmPOS-ORD
10h 29m1 stop
Multiple Airlines Logo
7:20 am - 1:11 pmORD-POS
27h 51m2 stops
$673Multiple Airlines
Find Deal
sáb., dic. 20 - jue., ene. 1

Air Canada flights from Trinidad and Tobago to Chicago

Our best Air Canada deals on Trinidad and Tobago to Chicago flight tickets
Air Canada
Nov 25
POS2:15 amPort of Spain Piarco Intl
12h 46m
1 stop
ORD1:01 pmChicago O'Hare Intl
Dec 1
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
$471
Find similar
Air Canada
Nov 13
POS2:15 amPort of Spain Piarco Intl
19h 15m
1 stop
ORD7:30 pmChicago O'Hare Intl
Nov 26
ORD3:55 pmChicago O'Hare Intl
31h 15m
1 stop
POS1:10 amPort of Spain Piarco Intl
$483
Find similar
Air Canada
Feb 26
POS2:15 amPort of Spain Piarco Intl
19h 15m
1 stop
ORD7:30 pmChicago O'Hare Intl
Mar 3
ORD2:00 pmChicago O'Hare Intl
9h 10m
1 stop
POS1:10 amPort of Spain Piarco Intl
$539
Find similar

Copa Airlines flights from Trinidad and Tobago to Chicago

Our best Copa Airlines deals on Trinidad and Tobago to Chicago flight tickets
Copa Airlines
Nov 14
POS2:26 pmPort of Spain Piarco Intl
11h 39m
1 stop
ORD12:05 amChicago O'Hare Intl
Nov 26
ORD6:56 amChicago O'Hare Intl
16h 52m
1 stop
POS1:48 amPort of Spain Piarco Intl
$562
Find similar
Copa Airlines
Feb 27
POS2:16 pmPort of Spain Piarco Intl
24h 15m
1 stop
ORD12:31 pmChicago O'Hare Intl
Mar 3
ORD7:34 amChicago O'Hare Intl
27h 41m
1 stop
POS1:15 pmPort of Spain Piarco Intl
$653
Find similar
Copa Airlines
Feb 27
POS2:16 pmPort of Spain Piarco Intl
24h 15m
1 stop
ORD12:31 pmChicago O'Hare Intl
Mar 3
ORD2:22 pmChicago O'Hare Intl
20h 53m
1 stop
POS1:15 pmPort of Spain Piarco Intl
$670
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated octubre 27, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 11/25

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

lun. 12/1

8:15 pm-1:10 am

1 stop26h 55m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

jue. 11/13

2:15 am-7:30 pm

1 stop19h 15m

Chicago O'Hare Intl

mié. 11/26

3:55 pm-1:10 am

1 stop31h 15m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

vie. 11/14

2:26 pm-12:05 am

1 stop11h 39m

Chicago O'Hare Intl

mié. 11/26

6:56 am-1:48 am

1 stop16h 52m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

sáb. 12/20

1:30 am-10:58 am

1 stop11h 28m

Chicago O'Hare Intl

jue. 1/1

5:49 am-12:23 am

1 stop16h 34m

$572

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

sáb. 11/22

1:30 am-10:56 am

1 stop11h 26m

Chicago O'Hare Intl

dom. 11/30

10:36 am-12:23 am

1 stop11h 47m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mié. 11/26

7:19 am-6:17 pm

1 stop12h 58m

Chicago O'Hare Intl

dom. 11/30

12:52 am-3:30 pm

2 stops12h 38m

$579

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

dom. 11/23

4:30 pm-9:05 am

1 stop18h 35m

Chicago O'Hare Intl

dom. 11/30

7:17 pm-3:30 pm

1 stop18h 13m

$622

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

sáb. 12/20

10:10 am-6:39 pm

1 stop10h 29m

Chicago O'Hare Intl

mié. 12/31

5:45 am-8:20 pm

2 stops12h 35m

$649

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

vie. 2/27

2:16 pm-12:31 pm

1 stop24h 15m

Chicago O'Hare Intl

mar. 3/3

7:34 am-1:15 pm

1 stop27h 41m

$653

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

sáb. 12/20

10:10 am-6:39 pm

1 stop10h 29m

Chicago O'Hare Intl

jue. 1/1

7:20 am-1:11 pm

2 stops27h 51m

$673

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Trinidad and Tobago 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 Tuesday when prices can be found for as low as $597. 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 Trinidad and Tobago 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 Trinidad and Tobago 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.

Cheap Trinidad and Tobago to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Trinidad and Tobago to Chicago

Direct flights

None
There are no direct flights from Trinidad and Tobago to Chicago. There are no popular flight routes from Trinidad and Tobago to Chicago.
Search flight deals

  • When did momondo last update prices for flights from Trinidad and Tobago to Chicago?

    Prices for flights from Trinidad and Tobago to Chicago refresh daily.

  • How many operators does momondo search for flights from Trinidad and Tobago to Chicago?

  • How old do you have to be to fly from Trinidad and Tobago to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Trinidad and Tobago to Chicago.

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Trinidad and Tobago to Chicago

Compare and see reviews for airlines that fly from Trinidad and Tobago to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $299Free CancellationRating
7.6
1,561 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
8,999 reviews
Search United Airlines flights
American AirlinesPriceFrom $561Free CancellationRating
7.2
11,031 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Trinidad and Tobago to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Trinidad and Tobago to Chicago for you.

Can I find flights from Trinidad and Tobago to Chicago with flexible booking policies on momondo?

All flight searches from Trinidad and Tobago to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Trinidad and Tobago to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Trinidad and Tobago.

I’m not ready to book a flight from Trinidad and Tobago to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Trinidad and Tobago to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport