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Cheap flights from Chicago Midway Airport to Caribbean Islands 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 Chicago Midway Airport to Caribbean Islands departing on 5/11. 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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Find the cheapest flights from Chicago Midway Airport to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:14 am - 10:48 pm
MDW
-
SJU
12h 34m
1 stop
Frontier Logo
3:08 am - 4:00 pm
SJU
-
MDW
13h 52m
1 stop
$221Frontier
Fri, Apr 17 - Fri, Apr 17
Frontier Logo
11:33 am - 2:01 am
MDW
-
SJU
13h 28m
1 stop
Frontier Logo
3:03 am - 3:57 pm
SJU
-
MDW
13h 54m
1 stop
$223Frontier
Fri, May 1 - Thu, May 7
Frontier Logo
5:30 am - 8:00 pm
MDW
-
SJU
13h 30m
1 stop
Frontier Logo
3:19 pm - 4:00 pm
SJU
-
MDW
25h 41m
1 stop
$226Frontier
Mon, Apr 13 - Fri, Apr 17
Multiple Airlines Logo
6:30 am - 11:58 pm
MDW
-
SJU
16h 28m
1 stop
Multiple Airlines Logo
11:30 am - 6:37 pm
SJU
-
MDW
32h 07m
2 stops
$228Multiple Airlines
Mon, Apr 13 - Fri, Apr 17
Frontier Logo
6:00 am - 2:01 am
MDW
-
SJU
19h 01m
1 stop
Frontier Logo
3:08 am - 4:00 pm
SJU
-
MDW
13h 52m
1 stop
$230Frontier
Sat, Apr 11 - Fri, Apr 17
Multiple Airlines Logo
6:30 am - 11:58 pm
MDW
-
SJU
16h 28m
1 stop
Multiple Airlines Logo
11:02 am - 10:26 pm
SJU
-
MDW
12h 24m
1 stop
$242Multiple Airlines
Mon, Apr 13 - Fri, Apr 17
Southwest Logo
10:05 am - 1:55 pm
MDW
-
MBJ
3h 50mnonstop
Southwest Logo
1:50 pm - 5:50 pm
MBJ
-
MDW
4h 00mnonstop
$318Southwest
Fri, Jul 3 - Tue, Jul 7
Southwest Logo
5:15 am - 2:20 pm
MDW
-
MBJ
9h 05m
1 stop
Southwest Logo
12:15 pm - 8:15 pm
MBJ
-
MDW
8h 00m
2 stops
$367Southwest
Sun, May 3 - Thu, May 7
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:37 pm - 10:28 pm
SDQ
-
MDW
8h 51m
1 stop
$481Delta
Sat, Apr 25 - Sat, May 2
Delta Logo
6:00 am - 1:12 pm
MDW
-
SDQ
6h 12m
1 stop
Delta Logo
2:37 pm - 10:28 pm
SDQ
-
MDW
8h 51m
1 stop
$482Delta
Sat, Apr 25 - Sat, May 2

Frontier flights from Chicago Midway Airport to Caribbean Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier
Apr 10
MDW2:56 pmChicago Midway
8h 56m
1 stop
SJU12:52 amSan Juan Luis Munoz Marin Intl
Apr 17
SJU3:08 amSan Juan Luis Munoz Marin Intl
13h 52m
1 stop
MDW4:00 pmChicago Midway
$220
Frontier
Apr 17
MDW9:14 amChicago Midway
12h 34m
1 stop
SJU10:48 pmSan Juan Luis Munoz Marin Intl
Apr 17
SJU3:08 amSan Juan Luis Munoz Marin Intl
13h 52m
1 stop
MDW4:00 pmChicago Midway
$221
Frontier
May 1
MDW11:33 amChicago Midway
13h 28m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
May 7
SJU3:03 amSan Juan Luis Munoz Marin Intl
13h 54m
1 stop
MDW3:57 pmChicago Midway
$223

Southwest flights from Chicago Midway Airport to Caribbean Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest
Jul 3
MDW10:05 amChicago Midway
3h 50m
MBJ1:55 pmMontego Bay Sangster Intl
Jul 7
MBJ1:50 pmMontego Bay Sangster Intl
4h 00m
MDW5:50 pmChicago Midway
$318
Southwest
Apr 12
MDW7:35 amChicago Midway
6h 05m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
May 12
SJU5:05 amSan Juan Luis Munoz Marin Intl
12h 10m
1 stop
MDW4:15 pmChicago Midway
$346
Southwest
May 3
MDW5:15 amChicago Midway
9h 05m
1 stop
MBJ2:20 pmMontego Bay Sangster Intl
May 7
MBJ12:15 pmMontego Bay Sangster Intl
8h 00m
2 stops
MDW8:15 pmChicago Midway
$367

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Caribbean 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 April 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/17

9:14 am-10:48 pm

1 stop12h 34m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:08 am-4:00 pm

1 stop13h 52m

$221

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/1

11:33 am-2:01 am

1 stop13h 28m

San Juan Luis Munoz Marin Intl

Thu 5/7

3:03 am-3:57 pm

1 stop13h 54m

$223

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/13

5:30 am-8:00 pm

1 stop13h 30m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:19 pm-4:00 pm

1 stop25h 41m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/13

6:30 am-11:58 pm

1 stop16h 28m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:30 am-6:37 pm

2 stops32h 07m

$228

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 4/11

6:00 am-2:01 am

1 stop19h 01m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:08 am-4:00 pm

1 stop13h 52m

$230

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 4/13

6:30 am-11:58 pm

1 stop16h 28m

San Juan Luis Munoz Marin Intl

Fri 4/17

11:02 am-10:26 pm

1 stop12h 24m

$242
Quickest round-trip

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Fri 7/3

10:05 am-1:55 pm

Nonstop3h 50m

Montego Bay Sangster Intl

Tue 7/7

1:50 pm-5:50 pm

Nonstop4h 00m

$318

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 5/3

5:15 am-2:20 pm

1 stop9h 05m

Montego Bay Sangster Intl

Thu 5/7

12:15 pm-8:15 pm

2 stops8h 00m

$367

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 4/25

6:00 am-1:12 pm

1 stop6h 12m

Santo Domingo Las Americas

Sat 5/2

2:37 pm-10:28 pm

1 stop8h 51m

$481

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Sat 4/25

6:00 am-1:12 pm

1 stop6h 12m

Santo Domingo Las Americas

Sat 5/2

2:37 pm-10:28 pm

1 stop8h 51m

$482

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 Caribbean Islands from

How to get the cheapest flight ticket from Chicago Midway Airport to Caribbean 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 month to fly to Caribbean Islands?

The month of February is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $271. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $304.

What is the cheapest Chicago Midway to Caribbean Islands flight route?

Fly from Chicago Midway to San Juan Luis Munoz Marin Intl for the best Chicago Midway - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $384 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Chicago Midway Airport for as low as $262 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway to Caribbean Islands 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 Chicago Midway Airport to Caribbean Islands flights?

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

Cheap Chicago Midway Airport to Caribbean Islands flight deals and tips

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

Fastest flight time

3h 50m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 3h 50m
Direct flights go from Chicago Midway Airport to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Chicago Midway Airport there are direct flights to Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Caribbean Islands

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

    Prices for flights from Chicago Midway Airport to Caribbean Islands were last updated today.

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

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

    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 Chicago Midway Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The necessary travel and health documents for your Caribbean 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.

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

Best airlines flying from Chicago Midway Airport to Caribbean Islands

Compare and see reviews for airlines that fly from Chicago Midway Airport to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $132Free CancellationRating
7.9
8,366 reviews
Search Delta flights
FrontierPriceFrom $142Free CancellationRating
5.7
3,004 reviews
Search Frontier flights
SouthwestPriceFrom $377Free CancellationRating
8.0
4,337 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean Islands?

Finding the right flight to Caribbean Islands from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

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

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

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

momondo provides multiple filters to help you find the best flight to Caribbean 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 Caribbean Islands right now. Can momondo alert me if prices change?

Price alerts on flights to Caribbean Islands from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Caribbean Islands trip

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