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Cheap flights from Caribbean to Chicago from $107

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Chicago departing on 4/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Caribbean to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:13 pm
MDW
-
SJU
7h 13m
1 stop
$202Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
3:19 pm - 4:13 pm
SJU
-
MDW
25h 54m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$213Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
$223Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
9:14 am - 2:01 am
MDW
-
SJU
15h 47m
1 stop
$234Frontier
Fri, Apr 24 - Mon, Apr 27
Delta Logo
7:30 am - 4:26 pm
SJU
-
MDW
9h 56m
1 stop
Delta Logo
10:41 am - 8:24 pm
MDW
-
SJU
8h 43m
1 stop
$246Delta
Sat, Apr 18 - Tue, Apr 21
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
7:30 am - 4:29 pm
MDW
-
SDQ
31h 59m
2 stops
$341Multiple Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
6:10 am - 1:00 pm
SDQ
-
MDW
7h 50m
1 stop
Multiple Airlines Logo
2:20 pm - 4:29 pm
MDW
-
SDQ
25h 09m
2 stops
$352Multiple Airlines
Tue, May 5 - Tue, May 12
Southwest Logo
2:35 pm - 6:40 pm
PUJ
-
MDW
5h 05mnonstop
Southwest Logo
9:15 am - 2:30 pm
MDW
-
PUJ
4h 15mnonstop
$450Southwest
Tue, Mar 24 - Tue, Mar 31
Delta Logo
6:10 pm - 10:31 pm
NAS
-
MDW
5h 21m
1 stop
Delta Logo
10:45 am - 4:45 pm
MDW
-
NAS
5h 00m
1 stop
$465Delta
Wed, Apr 1 - Tue, Apr 7
Southwest Logo
1:25 pm - 10:40 pm
PUJ
-
MDW
10h 15m
1 stop
Southwest Logo
9:15 am - 2:30 pm
MDW
-
PUJ
4h 15mnonstop
$467Southwest
Tue, Mar 24 - Tue, Mar 31

Frontier flights from Caribbean to Chicago Midway Airport

Our best Frontier deals on Caribbean to Chicago Midway Airport flight tickets
Frontier
May 1
SJU3:23 pmSan Juan Luis Munoz Marin Intl
8h 03m
1 stop
MDW10:26 pmChicago Midway
May 4
MDW6:00 amChicago Midway
7h 13m
1 stop
SJU2:13 pmSan Juan Luis Munoz Marin Intl
$202
Frontier
May 8
SJU3:19 pmSan Juan Luis Munoz Marin Intl
25h 54m
1 stop
MDW4:13 pmChicago Midway
May 11
MDW9:14 amChicago Midway
15h 47m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
$213
Frontier
May 7
SJU3:18 pmSan Juan Luis Munoz Marin Intl
8h 01m
1 stop
MDW10:19 pmChicago Midway
May 10
MDW9:14 amChicago Midway
12h 34m
1 stop
SJU10:48 pmSan Juan Luis Munoz Marin Intl
$223

Southwest flights from Caribbean to Chicago Midway Airport

Our best Southwest deals on Caribbean to Chicago Midway Airport flight tickets
Southwest
May 7
SJU1:00 pmSan Juan Luis Munoz Marin Intl
8h 50m
1 stop
MDW8:50 pmChicago Midway
May 10
MDW1:45 pmChicago Midway
9h 20m
2 stops
SJU12:05 amSan Juan Luis Munoz Marin Intl
$281
Southwest
Apr 17
SJU6:50 amSan Juan Luis Munoz Marin Intl
14h 45m
2 stops
MDW8:35 pmChicago Midway
Apr 20
MDW1:00 pmChicago Midway
9h 25m
1 stop
SJU11:25 pmSan Juan Luis Munoz Marin Intl
$311
Southwest
May 7
SJU5:35 amSan Juan Luis Munoz Marin Intl
8h 30m
2 stops
MDW1:05 pmChicago Midway
May 10
MDW1:45 pmChicago Midway
9h 20m
2 stops
SJU12:05 amSan Juan Luis Munoz Marin Intl
$346

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Chicago Midway Airport 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 February 26, 2026.
Use the filters below to find and compare flights from Caribbean to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/1

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 5/4

6:00 am-2:13 pm

1 stop7h 13m

$202

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 5/8

3:19 pm-4:13 pm

1 stop25h 54m

Chicago Midway

Mon 5/11

9:14 am-2:01 am

1 stop15h 47m

$213

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/7

3:18 pm-10:19 pm

1 stop8h 01m

Chicago Midway

Sun 5/10

9:14 am-10:48 pm

1 stop12h 34m

$223

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 4/24

3:23 pm-10:26 pm

1 stop8h 03m

Chicago Midway

Mon 4/27

9:14 am-2:01 am

1 stop15h 47m

$234

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Sat 4/18

7:30 am-4:26 pm

1 stop9h 56m

Chicago Midway

Tue 4/21

10:41 am-8:24 pm

1 stop8h 43m

$246

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 5/5

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Tue 5/12

7:30 am-4:29 pm

2 stops31h 59m

$341

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Tue 5/5

6:10 am-1:00 pm

1 stop7h 50m

Chicago Midway

Tue 5/12

2:20 pm-4:29 pm

2 stops25h 09m

$352

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 3/24

2:35 pm-6:40 pm

Nonstop5h 05m

Chicago Midway

Tue 3/31

9:15 am-2:30 pm

Nonstop4h 15m

$450

NassauChicago

NAS - MDW

NASMDW

Nassau Intl

Wed 4/1

6:10 pm-10:31 pm

1 stop5h 21m

Chicago Midway

Tue 4/7

10:45 am-4:45 pm

1 stop5h 00m

$465

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Tue 3/24

1:25 pm-10:40 pm

1 stop10h 15m

Chicago Midway

Tue 3/31

9:15 am-2:30 pm

Nonstop4h 15m

$467

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 Chicago from

How to get the cheapest flight ticket from Caribbean to Chicago Midway Airport

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 month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Caribbean, with most prices found around $302. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Caribbean during the month November is also very affordable. Most momondo users find prices during this month for around $336.

What is the cheapest Caribbean to Chicago Midway flight route?

Fly from Montego Bay Sangster Intl to Chicago Midway for the best Caribbean - Chicago Midway flight prices

What cabin class options are available on Caribbean to Chicago Midway flights?

There is only 1 cabin class available to choose from on Caribbean to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Caribbean to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Caribbean to Chicago Midway Airport.

Cheap Caribbean to Chicago Midway Airport flight deals and tips

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

Fastest flight time

4h 45m

Direct flights

Every day
The fastest flight from Caribbean to Chicago Midway Airport takes 4h 45m
Direct flights go from Caribbean to Chicago Midway Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Caribbean to Chicago Midway Airport?

    Prices for flights from Caribbean to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Caribbean to Chicago Midway Airport?

  • How old do you have to be to fly from Caribbean to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Caribbean to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport 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.

  • What is the most popular plane model from Caribbean to Chicago Midway Airport?

Best airlines flying from Caribbean to Chicago Midway Airport

Compare and see reviews for airlines that fly from Caribbean to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $392Free CancellationRating
8.0
4,299 reviews
Search Southwest 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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Caribbean 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 Caribbean to Chicago for you.

Can I find flights from Caribbean to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Caribbean on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Caribbean to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Caribbean to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Caribbean. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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