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Cheap flights from Caribbean to Chicago from $108

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 2/6. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
4:35 pm - 10:13 pm
SJU
-
MDW
7h 38m1 stop
Frontier Logo
6:10 am - 3:27 pm
MDW
-
SJU
7h 17m1 stop
$167Frontier
Sat, Jan 17 - Mon, Jan 19
Frontier Logo
4:11 pm - 11:25 pm
SJU
-
MDW
9h 14m1 stop
Frontier Logo
7:00 am - 7:32 pm
MDW
-
SJU
11h 32m1 stop
$180Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
10:47 pm - 2:06 pm
SJU
-
MDW
17h 19m1 stop
Frontier Logo
4:31 pm - 2:50 am
MDW
-
SJU
8h 19m1 stop
$181Frontier
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
5:47 pm - 12:05 pm
PUJ
-
MDW
20h 18m2 stops
Multiple Airlines Logo
1:00 pm - 6:00 pm
MDW
-
PUJ
27h 00m1 stop
$319Multiple Airlines
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
5:47 pm - 12:05 pm
PUJ
-
MDW
20h 18m2 stops
Multiple Airlines Logo
1:00 pm - 6:00 pm
MDW
-
PUJ
27h 00m1 stop
$321Multiple Airlines
Mon, Jan 26 - Mon, Feb 2
Delta Logo
12:38 pm - 10:22 pm
MBJ
-
MDW
10h 44m1 stop
Delta Logo
6:00 am - 12:54 pm
MDW
-
MBJ
5h 54m1 stop
$346Delta
Wed, Jan 21 - Wed, Jan 28
Delta Logo
7:30 am - 10:22 pm
SDQ
-
MDW
16h 52m2 stops
Delta Logo
6:00 am - 12:32 am
MDW
-
SDQ
16h 32m2 stops
$392Delta
Wed, Jan 28 - Wed, Feb 18
Southwest Logo
1:30 pm - 10:35 pm
GCM
-
MDW
10h 05m2 stops
Southwest Logo
9:40 pm - 12:35 pm
MDW
-
GCM
13h 55m2 stops
$851Southwest
Thu, Dec 25 - Mon, Dec 29
WestJet Logo
2:55 pm - 5:55 pm
MBJ
-
MDW
28h 00m2 stops
WestJet Logo
9:33 am - 7:23 pm
MDW
-
MBJ
32h 50m2 stops
$1,104WestJet
Thu, Jan 22 - Mon, Jan 26
WestJet Logo
1:55 pm - 6:05 pm
MBJ
-
MDW
28h 10m2 stops
WestJet Logo
10:35 am - 12:49 pm
MDW
-
MBJ
26h 14m2 stops
$1,186WestJet
Wed, Apr 15 - Tue, Apr 21

Frontier flights from Caribbean to Chicago Midway Airport

Our best Frontier deals on Caribbean to Chicago Midway Airport flight tickets
Frontier
Jan 17
SJU4:35 pmSan Juan Luis Munoz Marin Intl
7h 38m
1 stop
MDW10:13 pmChicago Midway
Jan 19
MDW6:10 amChicago Midway
7h 17m
1 stop
SJU3:27 pmSan Juan Luis Munoz Marin Intl
$167
Find similar
Frontier
Mar 5
SJU4:11 pmSan Juan Luis Munoz Marin Intl
9h 14m
1 stop
MDW11:25 pmChicago Midway
Mar 9
MDW7:00 amChicago Midway
11h 32m
1 stop
SJU7:32 pmSan Juan Luis Munoz Marin Intl
$180
Find similar
Frontier
Jan 8
SJU10:47 pmSan Juan Luis Munoz Marin Intl
17h 19m
1 stop
MDW2:06 pmChicago Midway
Jan 12
MDW4:31 pmChicago Midway
8h 19m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
$181
Find similar

Delta flights from Caribbean to Chicago Midway Airport

Our best Delta deals on Caribbean to Chicago Midway Airport flight tickets
Delta
Jan 21
MBJ12:38 pmMontego Bay Sangster Intl
10h 44m
1 stop
MDW10:22 pmChicago Midway
Jan 28
MDW6:00 amChicago Midway
5h 54m
1 stop
MBJ12:54 pmMontego Bay Sangster Intl
$346
Find similar
Delta
Jan 21
PUJ4:55 pmPunta Cana
17h 57m
2 stops
MDW8:52 amChicago Midway
Feb 4
MDW6:00 amChicago Midway
7h 30m
1 stop
PUJ3:30 pmPunta Cana
$362
Find similar
Delta
Jan 23
PUJ4:55 pmPunta Cana
7h 27m
1 stop
MDW10:22 pmChicago Midway
Jan 30
MDW6:00 amChicago Midway
7h 30m
1 stop
PUJ3:30 pmPunta Cana
$368
Find similar

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 December 9, 2025.
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

Sat 1/17

4:35 pm-10:13 pm

1 stop7h 38m

Chicago Midway

Mon 1/19

6:10 am-3:27 pm

1 stop7h 17m

$167

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-11:25 pm

1 stop9h 14m

Chicago Midway

Mon 3/9

7:00 am-7:32 pm

1 stop11h 32m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/8

10:47 pm-2:06 pm

1 stop17h 19m

Chicago Midway

Mon 1/12

4:31 pm-2:50 am

1 stop8h 19m

$181

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 1/26

5:47 pm-12:05 pm

2 stops20h 18m

Chicago Midway

Mon 2/2

1:00 pm-6:00 pm

1 stop27h 00m

$319

Punta CanaChicago

PUJ - MDW

PUJMDW

Punta Cana

Mon 1/26

5:47 pm-12:05 pm

2 stops20h 18m

Chicago Midway

Mon 2/2

1:00 pm-6:00 pm

1 stop27h 00m

$321

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 1/21

12:38 pm-10:22 pm

1 stop10h 44m

Chicago Midway

Wed 1/28

6:00 am-12:54 pm

1 stop5h 54m

$346

Santo DomingoChicago

SDQ - MDW

SDQMDW

Santo Domingo Las Americas

Wed 1/28

7:30 am-10:22 pm

2 stops16h 52m

Chicago Midway

Wed 2/18

6:00 am-12:32 am

2 stops16h 32m

$392

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/25

1:30 pm-10:35 pm

2 stops10h 05m

Chicago Midway

Mon 12/29

9:40 pm-12:35 pm

2 stops13h 55m

$851

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Thu 1/22

2:55 pm-5:55 pm

2 stops28h 00m

Chicago Midway

Mon 1/26

9:33 am-7:23 pm

2 stops32h 50m

$1,104

Montego BayChicago

MBJ - MDW

MBJMDW

Montego Bay Sangster Intl

Wed 4/15

1:55 pm-6:05 pm

2 stops28h 10m

Chicago Midway

Tue 4/21

10:35 am-12:49 pm

2 stops26h 14m

$1,186

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 $297. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Caribbean during the month February is also very affordable. Most momondo users find prices during this month for around $325.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Caribbean. The lowest ticket price found for a Friday departure recently was $154. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $610.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Caribbean in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $580. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Caribbean to Chicago Midway flight route?

Fly from San Juan Luis Munoz Marin 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

Mon, Thu, Fri, Sat and Sun
The fastest flight from Caribbean to Chicago Midway Airport takes 4h 45m
Direct flights go from Caribbean to Chicago Midway Airport on Monday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
4,254 reviews
Search Southwest flights
DeltaPriceFrom $505Free CancellationRating
7.9
8,011 reviews
Search Delta 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
Crown Point
Munster
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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