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Cheap flights from Chicago Midway Airport to Caribbean Islands from $113

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 8/11. 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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Find the cheapest flights from Chicago Midway Airport to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
1:45 pm - 9:00 pm
SJU
-
MDW
8h 15m
1 stop
$236Southwest
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
7:15 am - 4:55 pm
MDW
-
SJU
8h 40m
1 stop
Southwest Logo
5:55 am - 4:40 pm
SJU
-
MDW
11h 45m
1 stop
$246Southwest
Thu, Aug 20 - Sat, Aug 29
Delta Logo
10:54 am - 10:29 pm
MDW
-
SJU
10h 35m
1 stop
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
$256Delta
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
5:05 am - 1:10 pm
SJU
-
MDW
9h 05m
2 stops
$266Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
Southwest Logo
8:55 pm - 8:45 am
SJU
-
MDW
12h 50m
1 stop
$276Southwest
Thu, Aug 27 - Thu, Sep 3
Frontier Logo
6:00 am - 2:29 pm
MDW
-
PUJ
7h 29m
1 stop
Frontier Logo
3:39 pm - 11:09 am
PUJ
-
MDW
20h 30m
1 stop
$443Frontier
Tue, Aug 25 - Tue, Sep 1
Delta Logo
6:05 am - 3:34 pm
MDW
-
MBJ
9h 29m
1 stop
Delta Logo
1:09 pm - 10:36 pm
MBJ
-
MDW
9h 27m
1 stop
$452Delta
Sun, Aug 16 - Wed, Aug 26
Frontier Logo
6:00 am - 2:24 pm
MDW
-
PUJ
7h 24m
1 stop
Frontier Logo
11:42 am - 10:11 pm
PUJ
-
MDW
11h 29m
2 stops
$454Frontier
Sat, Jun 6 - Wed, Jun 10
Multiple Airlines Logo
6:00 am - 2:29 pm
MDW
-
PUJ
7h 29m
1 stop
Multiple Airlines Logo
1:01 pm - 10:58 am
PUJ
-
MDW
22h 57m
2 stops
$478Multiple Airlines
Tue, Sep 8 - Fri, Sep 11
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
7:00 am - 10:11 pm
GCM
-
MDW
15h 11m
2 stops
$565Multiple Airlines
Thu, Jun 4 - Thu, Jun 11

Southwest flights from Chicago Midway Airport to Caribbean Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest
Aug 19
MDW12:45 pmChicago Midway
8h 15m
2 stops
SJU10:00 pmSan Juan Luis Munoz Marin Intl
Aug 26
SJU1:45 pmSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
MDW9:00 pmChicago Midway
$236
Southwest
Aug 20
MDW7:15 amChicago Midway
8h 40m
1 stop
SJU4:55 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU5:55 amSan Juan Luis Munoz Marin Intl
11h 45m
1 stop
MDW4:40 pmChicago Midway
$246
Southwest
Aug 19
MDW12:45 pmChicago Midway
8h 15m
1 stop
SJU10:00 pmSan Juan Luis Munoz Marin Intl
Aug 22
SJU5:05 amSan Juan Luis Munoz Marin Intl
9h 05m
2 stops
MDW1:10 pmChicago Midway
$266

Delta flights from Chicago Midway Airport to Caribbean Islands

Our best Delta deals on Chicago Midway Airport to Caribbean Islands flight tickets
Delta
Aug 12
MDW10:54 amChicago Midway
10h 35m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 19
SJU12:56 pmSan Juan Luis Munoz Marin Intl
10h 40m
1 stop
MDW10:36 pmChicago Midway
$256
Delta
Aug 25
MDW6:05 amChicago Midway
9h 32m
1 stop
SJU4:37 pmSan Juan Luis Munoz Marin Intl
Aug 29
SJU12:56 pmSan Juan Luis Munoz Marin Intl
10h 40m
1 stop
MDW10:36 pmChicago Midway
$326
Delta
Aug 20
MDW12:46 pmChicago Midway
8h 43m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 24
SJU12:56 pmSan Juan Luis Munoz Marin Intl
10h 40m
1 stop
MDW10:36 pmChicago Midway
$341

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 May 18, 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
Quickest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/19

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Wed 8/26

1:45 pm-9:00 pm

1 stop8h 15m

$236

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/20

7:15 am-4:55 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Sat 8/29

5:55 am-4:40 pm

1 stop11h 45m

$246

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/12

10:54 am-10:29 pm

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Wed 8/19

12:56 pm-10:36 pm

1 stop10h 40m

$256

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/19

12:45 pm-10:00 pm

2 stops8h 15m

San Juan Luis Munoz Marin Intl

Sat 8/22

5:05 am-1:10 pm

2 stops9h 05m

$266

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/27

3:15 pm-11:05 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Thu 9/3

8:55 pm-8:45 am

1 stop12h 50m

$276

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 8/25

6:00 am-2:29 pm

1 stop7h 29m

Punta Cana

Tue 9/1

3:39 pm-11:09 am

1 stop20h 30m

$443

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 8/16

6:05 am-3:34 pm

1 stop9h 29m

Montego Bay Sangster Intl

Wed 8/26

1:09 pm-10:36 pm

1 stop9h 27m

$452

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 6/6

6:00 am-2:24 pm

1 stop7h 24m

Punta Cana

Wed 6/10

11:42 am-10:11 pm

2 stops11h 29m

$454

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Tue 9/8

6:00 am-2:29 pm

1 stop7h 29m

Punta Cana

Fri 9/11

1:01 pm-10:58 am

2 stops22h 57m

$478

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/4

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Thu 6/11

7:00 am-10:11 pm

2 stops15h 11m

$565

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 May is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $172. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $190.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Chicago Midway Airport to Caribbean Islands is on a Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $499. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $581. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

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

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

How far in advance should I book a flight from Chicago Midway Airport 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 $386 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 $274 on momondo.

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
8,447 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.6
2,946 reviews
Search Frontier flights
SouthwestPriceFrom $352Free CancellationRating
7.9
4,288 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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