$253 Find Cheap Flights from Chicago to the Turks and Caicos Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to the Turks and Caicos Islands departing on 9/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Chicago to the Turks and Caicos Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to the Turks and Caicos Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to the Turks and Caicos Islands

Sun, Oct 25 - Wed, Oct 28
Air Canada Logo
10:57 am - 1:15 pm
ORD
-
PLS
49h 18m
2 stops
Air Canada Logo
2:15 pm - 11:07 am
PLS
-
ORD
21h 52m
1 stop
$464Air Canada
Sun, Oct 25 - Thu, Oct 29
Air Canada Logo
10:57 am - 1:15 pm
ORD
-
PLS
49h 18m
2 stops
Air Canada Logo
1:20 pm - 6:20 pm
PLS
-
ORD
30h 00m
2 stops
$469Air Canada
Sun, Oct 25 - Fri, Oct 30
Air Canada Logo
9:21 pm - 12:25 pm
ORD
-
PLS
14h 04m
1 stop
Air Canada Logo
2:15 pm - 2:52 pm
PLS
-
ORD
25h 37m
1 stop
$470Air Canada
Sat, Dec 12 - Sat, Dec 19
Southwest Logo
3:05 pm - 1:45 pm
MDW
-
PLS
21h 40m
2 stops
Southwest Logo
12:20 pm - 6:30 pm
PLS
-
MDW
7h 10m
1 stop
$616Southwest
Sat, Dec 12 - Sat, Dec 19
Southwest Logo
2:50 pm - 1:45 pm
MDW
-
PLS
21h 55m
2 stops
Southwest Logo
12:20 pm - 8:10 pm
PLS
-
MDW
8h 50m
2 stops
$626Southwest
Fri, Aug 14 - Wed, Aug 19
Delta Logo
6:05 am - 12:40 pm
MDW
-
PLS
5h 35m
1 stop
Delta Logo
2:05 pm - 10:36 pm
PLS
-
MDW
9h 31m
1 stop
$657Delta
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
5:00 am - 11:55 am
MDW
-
PLS
5h 55m
1 stop
Southwest Logo
12:50 pm - 8:55 pm
PLS
-
MDW
9h 05m
1 stop
$661Southwest
Sat, Oct 24 - Fri, Oct 30
Delta Logo
1:00 pm - 12:45 pm
MDW
-
PLS
22h 45m
2 stops
Delta Logo
2:05 pm - 10:10 pm
PLS
-
MDW
9h 05m
1 stop
$662Delta
Tue, Aug 11 - Tue, Aug 18
Delta Logo
6:05 am - 12:40 pm
MDW
-
PLS
5h 35m
1 stop
Delta Logo
2:05 pm - 10:36 pm
PLS
-
MDW
9h 31m
1 stop
$696Delta
Sat, Jul 25 - Sat, Aug 1
Delta Logo
6:00 am - 12:40 pm
MDW
-
PLS
5h 40m
1 stop
Delta Logo
3:45 pm - 10:15 pm
PLS
-
MDW
7h 30m
1 stop
$697Delta
Booking Insights

KAYAK's insights & trends for Chicago to the Turks and Caicos Islands flights

Get data-powered insights and trends into flights from Chicago to the Turks and Caicos Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to the Turks and Caicos Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Turks and Caicos Islands from Chicago found in the last 5 days was to Providenciales, at $682 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Providenciales (PLS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $682.

What is the cheapest time of day to fly to the Turks and Caicos Islands?

The average price for all round-trip flights from Chicago to the Turks and Caicos Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Turks and Caicos Islands is generally in the morning, when round-trip flights cost $748 on average. The most expensive time of day to fly to the Turks and Caicos Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $748.

Can I save money by flying with a layover from Chicago to the Turks and Caicos Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $607 on average.

What is the cheapest month to fly from Chicago to the Turks and Caicos Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to the Turks and Caicos Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to the Turks and Caicos Islands is March, when tickets cost $214 (return) on average. On the other hand, the most expensive months are August and September, when the average cost of round-trip tickets is $587 and $531 respectively.

What’s the cheapest day of the week to fly from Chicago to Turks and Caicos Islands?

The average price of all round-trip flights from Chicago to the Turks and Caicos Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Turks and Caicos Islands on a Monday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Saturday, and avoid Fridays for better deals.

How far in advance should I book a flight from Chicago to the Turks and Caicos Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to the Turks and Caicos Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to the Turks and Caicos Islands, you should book around 4 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$253
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Chicago O'Hare Airport to Providenciales

FAQs - booking Turks and Caicos Islands flights

  • How does KAYAK find such low prices on flights from Chicago to the Turks and Caicos Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to the Turks and Caicos Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to the Turks and Caicos Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to the Turks and Caicos Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to the Turks and Caicos Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to the Turks and Caicos Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to the Turks and Caicos Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to the Turks and Caicos Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Chicago and Turks and Caicos Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in the Turks and Caicos Islands, with an average flight time of 4h 14m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 flights.

Reviews of the top 5 airlines serving from Chicago to the Turks and Caicos Islands

 
Need help choosing which airline to fly with from Chicago to the Turks and Caicos Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4244 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

I'm 6'8" (2.03m) so more legroom would alwqys be appreciated, especially on long international flights. The food choices were underwhelming.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Everything you need to know for your flight from Chicago to the Turks and Caicos Islands

Cabin class types available on flights to the Turks and Caicos Islands

Cabin classes available on flights to the Turks and Caicos Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.