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Cheap flights from Chicago Midway Airport to Caribbean Islands from $100

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 2/21. 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.
Frontier Logo
3:10 pm - 11:16 am
MDW
-
SJU
18h 06m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$201Frontier
Mon, Jan 5 - Mon, Jan 12
Frontier Logo
6:15 am - 12:39 pm
MDW
-
SJU
28h 24m1 stop
Frontier Logo
11:05 am - 8:32 pm
SJU
-
MDW
11h 27m1 stop
$202Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
3:01 pm - 12:35 pm
MDW
-
SJU
19h 34m1 stop
Frontier Logo
5:45 am - 2:06 pm
SJU
-
MDW
10h 21m1 stop
$203Frontier
Wed, Jan 7 - Fri, Jan 9
Frontier Logo
6:15 am - 2:35 am
MDW
-
SJU
18h 20m1 stop
Frontier Logo
5:30 pm - 8:32 pm
SJU
-
MDW
29h 02m1 stop
$204Frontier
Thu, Feb 19 - Sun, Mar 1
Multiple Airlines Logo
5:01 pm - 2:52 pm
MDW
-
STT
19h 51m2 stops
Multiple Airlines Logo
3:57 pm - 7:52 pm
STT
-
MDW
29h 55m1 stop
$303Multiple Airlines
Fri, Jan 30 - Sat, Feb 7
Multiple Airlines Logo
5:01 pm - 2:52 pm
MDW
-
STT
19h 51m2 stops
Multiple Airlines Logo
3:57 pm - 7:52 pm
STT
-
MDW
29h 55m1 stop
$304Multiple Airlines
Fri, Jan 30 - Sat, Feb 7
Delta Logo
6:00 am - 2:21 pm
MDW
-
SDQ
6h 21m1 stop
Delta Logo
3:46 pm - 10:22 pm
SDQ
-
MDW
8h 36m1 stop
$390Delta
Fri, Jan 30 - Wed, Feb 4
Delta Logo
6:00 am - 12:54 pm
MDW
-
MBJ
5h 54m1 stop
Delta Logo
4:45 pm - 10:22 pm
MBJ
-
MDW
6h 37m1 stop
$391Delta
Mon, Feb 2 - Fri, Feb 6
Southwest Logo
5:30 am - 1:45 pm
MDW
-
PLS
7h 15m1 stop
Southwest Logo
2:40 pm - 9:00 pm
PLS
-
MDW
7h 20m1 stop
$410Southwest
Mon, Jan 19 - Fri, Jan 23
Southwest Logo
7:50 pm - 12:55 pm
MDW
-
GCM
16h 05m2 stops
Southwest Logo
1:50 pm - 10:05 pm
GCM
-
MDW
9h 15m2 stops
$411Southwest
Mon, Jan 26 - Fri, Jan 30

Frontier flights from Chicago Midway Airport to Caribbean Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier
Jan 5
MDW3:10 pmChicago Midway
18h 06m
1 stop
SJU11:16 amSan Juan Luis Munoz Marin Intl
Jan 12
SJU5:45 amSan Juan Luis Munoz Marin Intl
10h 21m
1 stop
MDW2:06 pmChicago Midway
$201
Find similar
Frontier
Feb 26
MDW6:15 amChicago Midway
28h 24m
1 stop
SJU12:39 pmSan Juan Luis Munoz Marin Intl
Mar 2
SJU11:05 amSan Juan Luis Munoz Marin Intl
11h 27m
1 stop
MDW8:32 pmChicago Midway
$202
Find similar
Frontier
Jan 7
MDW3:01 pmChicago Midway
19h 34m
1 stop
SJU12:35 pmSan Juan Luis Munoz Marin Intl
Jan 9
SJU5:45 amSan Juan Luis Munoz Marin Intl
10h 21m
1 stop
MDW2:06 pmChicago Midway
$203
Find similar

Southwest flights from Chicago Midway Airport to Caribbean Islands

Our best Southwest deals on Chicago Midway Airport to Caribbean Islands flight tickets
Southwest
Jan 25
MDW3:15 pmChicago Midway
7h 25m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU6:10 amSan Juan Luis Munoz Marin Intl
7h 25m
1 stop
MDW11:35 amChicago Midway
$225
Find similar
Southwest
Jan 26
MDW1:55 pmChicago Midway
8h 40m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU6:10 amSan Juan Luis Munoz Marin Intl
9h 45m
2 stops
MDW1:55 pmChicago Midway
$245
Find similar
Southwest
Jan 31
MDW8:15 amChicago Midway
4h 20m
PUJ2:35 pmPunta Cana
Feb 4
PUJ2:40 pmPunta Cana
8h 20m
1 stop
MDW9:00 pmChicago Midway
$391
Find similar

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 December 11, 2025.
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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/5

3:10 pm-11:16 am

1 stop18h 06m

San Juan Luis Munoz Marin Intl

Mon 1/12

5:45 am-2:06 pm

1 stop10h 21m

$201

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/26

6:15 am-12:39 pm

1 stop28h 24m

San Juan Luis Munoz Marin Intl

Mon 3/2

11:05 am-8:32 pm

1 stop11h 27m

$202

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 1/7

3:01 pm-12:35 pm

1 stop19h 34m

San Juan Luis Munoz Marin Intl

Fri 1/9

5:45 am-2:06 pm

1 stop10h 21m

$203

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 2/19

6:15 am-2:35 am

1 stop18h 20m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:30 pm-8:32 pm

1 stop29h 02m

$204

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 1/30

5:01 pm-2:52 pm

2 stops19h 51m

Saint Thomas Island Cyril E King

Sat 2/7

3:57 pm-7:52 pm

1 stop29h 55m

$303

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

Fri 1/30

5:01 pm-2:52 pm

2 stops19h 51m

Saint Thomas Island Cyril E King

Sat 2/7

3:57 pm-7:52 pm

1 stop29h 55m

$304

ChicagoSanto Domingo

MDW - SDQ

MDWSDQ

Chicago Midway

Fri 1/30

6:00 am-2:21 pm

1 stop6h 21m

Santo Domingo Las Americas

Wed 2/4

3:46 pm-10:22 pm

1 stop8h 36m

$390

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 2/2

6:00 am-12:54 pm

1 stop5h 54m

Montego Bay Sangster Intl

Fri 2/6

4:45 pm-10:22 pm

1 stop6h 37m

$391

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Mon 1/19

5:30 am-1:45 pm

1 stop7h 15m

Providenciales

Fri 1/23

2:40 pm-9:00 pm

1 stop7h 20m

$410

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/26

7:50 pm-12:55 pm

2 stops16h 05m

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-10:05 pm

2 stops9h 15m

$411

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 $328. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $339.

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 Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $59. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $526. 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 time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Chicago Midway Airport to Caribbean Islands in the evening for as low as $324. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $530. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 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 $424 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 $336 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

  • 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
FrontierPriceFrom $142Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
DeltaPriceFrom $325Free CancellationRating
7.9
8,008 reviews
Search Delta flights
SouthwestPriceFrom $381Free CancellationRating
7.9
4,252 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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