Find cheap flights from Chicago to Trinidad and Tobago

Find cheap flights from Chicago to Trinidad and Tobago

Round-trip
Economy
Chicago (CHI)
Trinidad and Tobago
Wed 5/27
Wed 6/3
Any month
Compare vs. KAYAK |
Search hundreds of travel sites at once for deals on flights to Trinidad and Tobago

Good to know

Low season

May Best time to beat the crowds with an average 5% drop in price.

High season

December Most popular time to fly with an average 11% increase in price.

Average price of a round-trip

$739 (avg. price over the last 2 weeks)

Good deal for a round-trip

$463 or less

FAQs for booking Chicago to Trinidad and Tobago flights

Are flight prices cheaper from Chicago to Trinidad and Tobago because of coronavirus (COVID-19)?

How does KAYAK’s flight Price Forecast tool help me choose the right time to buy?

Book cheap flights from Chicago to Trinidad and Tobago (round-trip)

Airports
Origin
Chicago
$379
only
$379
Destination
Scarborough
$466
only
$466
Port of Spain
$379
only
$379
Mon, Oct 19
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Sun, Oct 25
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
10h 14m
Trip: 7 days
Based on 0 reviews
Mon, Sep 21
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
7h 19m
Fri, Sep 25
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
9h 08m
Trip: 5 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 19,142 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
POS
FLL
Excellent 10.0

Pros: Vegetarian meal was delicious

Cons: Would be great if WiFi was available

RDU
BOS
Okay 5.6

Pros: Great crew!

Cons: Very small tray table space. Carry on fee should have been easier to see during purchase. If I'd noticed, I would have planned differently.

SJU
DCA
Okay 5.6

Pros: Some of the crew was decent others seemed annoyed they were doing their job.

Cons: Some of the crew was decent others seemed annoyed they were doing their job. Two of the employees serving the cabin could use an attitude adjustment. The crew was late in getting food out but for a four hour flight there is no value in flying anymore. Airlines are just trying to rake in as much money as possible. When are they going to be responsible for everyone getting sick like cruise ships are? They should hand out masks and sanitizer because airlines are one of the dirtiest public spaces that there is! Show up late and barely clean the plane between its third or fourth leg of the day.

SXM
JFK
Okay 4.3

Cons: They shouldn't allow sick ppl on the plane

JFK
LGB
Excellent 10.0

Pros: Disregarding all that’s going on around the world in present time out experience was great

Mon, Sep 21
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Fri, Sep 25
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
10h 14m
Trip: 5 days
Based on 0 reviews
Sun, Oct 18
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Sun, Oct 25
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
10h 14m
Trip: 8 days
Based on 0 reviews
Mon, Oct 19
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Fri, Oct 30
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
29h 30m
Trip: 12 days
Based on 0 reviews
Thu, Oct 22
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Fri, Oct 23
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
29h 30m
Trip: 2 days
Based on 0 reviews
Sun, Oct 18
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Tue, Oct 27
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
17h 24m
Trip: 10 days
Based on 0 reviews
Sun, Oct 18
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Fri, Oct 30
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
29h 30m
Trip: 13 days
Based on 0 reviews
Sun, Oct 18
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Thu, Oct 29
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
10h 14m
Trip: 12 days
Based on 0 reviews
Tue, Nov 3
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
27h 59m
Tue, Nov 10
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
13h 54m
Trip: 8 days
Based on 0 reviews
Tue, Nov 10
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
27h 59m
Tue, Nov 17
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
13h 54m
Trip: 8 days
Based on 0 reviews
Sun, Oct 18
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
7h 19m
Fri, Oct 30
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
9h 17m
Trip: 13 days
8.2Excellent Show reviews
Overall 8.2 Excellent
Based on 19,142 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
SJU
JFK
Excellent 10.0

Cons: Todo fue Exelente...

JFK
NAS
Mediocre 2.6

Pros: Snacks

Cons: We boarded the plane and got settled only to be told we had to get off because the computer on the plane did not work. Then we had a 3 hour delay and upon landing we had to wait in the tarmac for an hour. We Are on an enjoyable vacation for a few amount of days and lost a whole day just with our flight

SJU
FLL
Excellent 10.0

Cons: .

EWR
FLL
Excellent 8.4

Cons: My tv didn’t work throughout the whole flight.

MCO
PVD
Excellent 9.2

Pros: The extra leg room was great!

Tue, Oct 20
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
28h 59m
Thu, Oct 22
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
10h 14m
Trip: 3 days
Based on 0 reviews
Tue, Nov 3
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
36h 15m
Tue, Nov 10
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
13h 54m
Trip: 8 days
Based on 0 reviews
Sun, Oct 18
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
9h 55m
Wed, Oct 28
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
18h 57m
Trip: 11 days
Based on 0 reviews
Tue, Oct 20
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
24h 28m
Tue, Oct 27
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
12h 54m
Trip: 8 days
Based on 0 reviews
Tue, Aug 11
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
24h 54m
Sat, Aug 15
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
22h 44m
Trip: 5 days
Based on 0 reviews
Tue, Oct 20
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
8h 24m
Thu, Oct 29
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
9h 17m
Trip: 10 days
Based on 0 reviews
Sat, Oct 24
ORD
Chicago O'Hare Airport
TAB
Scarborough ANR Robinson Intl
27h 34m
Wed, Oct 28
TAB
Scarborough ANR Robinson Intl
ORD
Chicago O'Hare Airport
20h 59m
Trip: 5 days
Based on 0 reviews
Tue, Oct 20
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
24h 28m
Mon, Oct 26
POS
Port of Spain Piarco Intl
ORD
Chicago O'Hare Airport
10h 14m
Trip: 7 days
Based on 0 reviews

Book cheap flights from Chicago to Trinidad and Tobago (one-way)

Airports
Origin
Chicago
$273
only
$273
Destination
Port of Spain
$273
only
$273
Sat, Jun 27
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
37h 19m
Based on 0 reviews
Sun, Jun 28
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
38h 44m
Based on 0 reviews
Wed, Jun 24
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
34h 10m
Based on 0 reviews
Thu, Jun 25
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
11h 25m
Based on 0 reviews
Mon, Jun 22
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
30h 55m
Based on 0 reviews
Tue, Jun 23
ORD
Chicago O'Hare Airport
POS
Port of Spain Piarco Intl
11h 25m
Based on 0 reviews
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First