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Cheap flights from Chicago Midway Airport to the Turks and Caicos Islands from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to the Turks and Caicos Islands departing on 1/23. 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 Chicago Midway Airport to the Turks and Caicos Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 3:48 pm
MDW
-
PLS
8h 48m1 stop
Frontier Logo
4:50 pm - 11:25 pm
PLS
-
MDW
7h 35m1 stop
$299Frontier
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
6:00 am - 1:33 pm
MDW
-
PLS
6h 33m1 stop
Frontier Logo
2:50 pm - 11:42 pm
PLS
-
MDW
9h 52m1 stop
$366Frontier
Sat, Mar 7 - Sat, Mar 14
Southwest Logo
6:05 am - 1:45 pm
MDW
-
PLS
6h 40m1 stop
Southwest Logo
2:40 pm - 9:50 pm
PLS
-
MDW
8h 10m1 stop
$486Southwest
Sun, Feb 22 - Sat, Feb 28
Southwest Logo
9:35 pm - 1:45 pm
MDW
-
PLS
15h 10m2 stops
Southwest Logo
2:40 pm - 9:50 pm
PLS
-
MDW
8h 10m1 stop
$491Southwest
Sun, Feb 22 - Sat, Feb 28
Southwest Logo
5:00 am - 1:45 pm
MDW
-
PLS
7h 45m1 stop
Southwest Logo
2:40 pm - 9:00 pm
PLS
-
MDW
7h 20m1 stop
$510Southwest
Wed, Jan 7 - Mon, Jan 12
Delta Logo
6:00 am - 12:50 pm
MDW
-
PLS
5h 50m1 stop
Delta Logo
2:10 pm - 10:42 pm
PLS
-
MDW
9h 32m1 stop
$528Delta
Tue, Feb 10 - Thu, Feb 19
Southwest Logo
5:00 am - 1:45 pm
MDW
-
PLS
7h 45m1 stop
Southwest Logo
2:40 pm - 9:00 pm
PLS
-
MDW
7h 20m1 stop
$550Southwest
Fri, Jan 30 - Mon, Feb 2
Southwest Logo
7:50 pm - 1:45 pm
MDW
-
PLS
16h 55m2 stops
Southwest Logo
2:40 pm - 9:00 pm
PLS
-
MDW
7h 20m1 stop
$555Southwest
Wed, Jan 7 - Mon, Jan 12
Delta Logo
6:00 am - 2:25 pm
MDW
-
PLS
7h 25m1 stop
Delta Logo
2:10 pm - 10:07 pm
PLS
-
MDW
8h 57m1 stop
$558Delta
Thu, Jan 1 - Tue, Jan 6
Delta Logo
6:00 am - 12:50 pm
MDW
-
PLS
5h 50m1 stop
Delta Logo
3:50 pm - 8:53 am
PLS
-
MDW
18h 03m2 stops
$563Delta
Tue, Feb 10 - Mon, Feb 16

Frontier flights from Chicago Midway Airport to Turks and Caicos Islands

Our best Frontier deals on Chicago Midway Airport to Turks and Caicos Islands flight tickets
Frontier
Feb 14
MDW6:00 amChicago Midway
8h 48m
1 stop
PLS3:48 pmProvidenciales
Feb 21
PLS4:50 pmProvidenciales
7h 35m
1 stop
MDW11:25 pmChicago Midway
$299
Find similar
Frontier
Mar 7
MDW6:00 amChicago Midway
6h 33m
1 stop
PLS1:33 pmProvidenciales
Mar 14
PLS2:50 pmProvidenciales
9h 52m
1 stop
MDW11:42 pmChicago Midway
$366
Find similar

Southwest flights from Chicago Midway Airport to Turks and Caicos Islands

Our best Southwest deals on Chicago Midway Airport to Turks and Caicos Islands flight tickets
Southwest
Feb 22
MDW6:05 amChicago Midway
6h 40m
1 stop
PLS1:45 pmProvidenciales
Feb 28
PLS2:40 pmProvidenciales
8h 10m
1 stop
MDW9:50 pmChicago Midway
$486
Find similar
Southwest
Feb 22
MDW9:35 pmChicago Midway
15h 10m
2 stops
PLS1:45 pmProvidenciales
Feb 28
PLS2:40 pmProvidenciales
8h 10m
1 stop
MDW9:50 pmChicago Midway
$491
Find similar
Southwest
Jan 7
MDW5:00 amChicago Midway
7h 45m
1 stop
PLS1:45 pmProvidenciales
Jan 12
PLS2:40 pmProvidenciales
7h 20m
1 stop
MDW9:00 pmChicago Midway
$510
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Turks and Caicos Islands 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 December 5, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to the Turks and Caicos Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Sat 2/14

6:00 am-3:48 pm

1 stop8h 48m

Providenciales

Sat 2/21

4:50 pm-11:25 pm

1 stop7h 35m

$299

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Sat 3/7

6:00 am-1:33 pm

1 stop6h 33m

Providenciales

Sat 3/14

2:50 pm-11:42 pm

1 stop9h 52m

$366

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Sun 2/22

6:05 am-1:45 pm

1 stop6h 40m

Providenciales

Sat 2/28

2:40 pm-9:50 pm

1 stop8h 10m

$486

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Sun 2/22

9:35 pm-1:45 pm

2 stops15h 10m

Providenciales

Sat 2/28

2:40 pm-9:50 pm

1 stop8h 10m

$491

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Wed 1/7

5:00 am-1:45 pm

1 stop7h 45m

Providenciales

Mon 1/12

2:40 pm-9:00 pm

1 stop7h 20m

$510

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Tue 2/10

6:00 am-12:50 pm

1 stop5h 50m

Providenciales

Thu 2/19

2:10 pm-10:42 pm

1 stop9h 32m

$528

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Fri 1/30

5:00 am-1:45 pm

1 stop7h 45m

Providenciales

Mon 2/2

2:40 pm-9:00 pm

1 stop7h 20m

$550

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Wed 1/7

7:50 pm-1:45 pm

2 stops16h 55m

Providenciales

Mon 1/12

2:40 pm-9:00 pm

1 stop7h 20m

$555

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Thu 1/1

6:00 am-2:25 pm

1 stop7h 25m

Providenciales

Tue 1/6

2:10 pm-10:07 pm

1 stop8h 57m

$558

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Tue 2/10

6:00 am-12:50 pm

1 stop5h 50m

Providenciales

Mon 2/16

3:50 pm-8:53 am

2 stops18h 03m

$563

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Turks and Caicos Islands from

How to get the cheapest flight ticket from Chicago Midway Airport to Turks and Caicos Islands

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 airline that flies from Chicago Midway to Turks and Caicos Islands?

Frontier, Southwest, and Delta are the most popular carriers operating from Chicago Midway to Turks and Caicos Islands

Cheap Chicago Midway Airport to Turks and Caicos Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Turks and Caicos Islands

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to Turks and Caicos Islands takes 5h 25m
There are no direct flights from Chicago Midway Airport to Turks and Caicos Islands. There are no popular flight routes from Chicago Midway Airport to Turks and Caicos Islands.
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Turks and Caicos Islands?

    Prices for flights from Chicago Midway Airport to Turks and Caicos Islands are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to Turks and Caicos Islands?

    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 Chicago Midway Airport to Turks and Caicos Islands.

  • What documentation or ID do you need to fly to Turks and Caicos Islands?

    The necessary travel and health documents for your Turks and Caicos Islands 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.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Turks and Caicos Islands?

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 Chicago to Turks and Caicos Islands for you.

Can I find flights from Chicago to Turks and Caicos Islands with flexible booking policies on momondo?

momondo does allow users to show only those flights to Turks and Caicos Islands from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Turks and Caicos Islands?

momondo provides multiple filters to help you find the best flight to Turks and Caicos Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Of course. momondo tracks the price of Chicago to Turks and Caicos Islands 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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