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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 9/6. 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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Find the cheapest flights from Chicago Midway Airport to Caribbean Islands

Cheap round-trip flights

Frontier Logo
10:51 am - 7:18 pmMDW-SJU
7h 27m1 stop
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
$235Frontier
Find Deal
sáb., ago. 30 - vie., sep. 5
Frontier Logo
10:51 am - 11:59 pmMDW-SJU
12h 08m1 stop
Frontier Logo
3:39 am - 9:51 amSJU-MDW
7h 12m1 stop
$238Frontier
Find Deal
sáb., sep. 6 - vie., sep. 19
Southwest Logo
5:10 am - 2:05 pmMDW-PUJ
7h 55m1 stop
Southwest Logo
3:05 pm - 9:35 pmPUJ-MDW
7h 30m1 stop
$343Southwest
Find Deal
lun., sep. 1 - vie., sep. 5
Southwest Logo
11:40 am - 10:40 pmMDW-SJU
10h 00m1 stop
Southwest Logo
7:45 am - 3:35 pmSJU-MDW
8h 50m2 stops
$351Southwest
Find Deal
sáb., sep. 6 - sáb., sep. 13
Delta Logo
6:00 am - 2:31 pmMDW-PUJ
7h 31m1 stop
Delta Logo
4:56 pm - 10:14 pmPUJ-MDW
7h 18m1 stop
$376Delta
Find Deal
dom., oct. 26 - dom., nov. 2
Delta Logo
6:00 am - 3:34 pmMDW-MBJ
9h 34m1 stop
Delta Logo
4:59 pm - 12:28 pmMBJ-MDW
19h 29m2 stops
$389Delta
Find Deal
dom., sep. 21 - vie., sep. 26
Logo
4:56 pm - 9:44 amMDW-STT
15h 48m2 stops
Logo
10:49 am - 11:20 pmSTT-MDW
13h 31m2 stops
$586
Find Deal
jue., sep. 18 - dom., sep. 21
Logo
8:39 am - 4:25 pmMDW-NAS
6h 46m1 stop
Logo
12:00 pm - 12:11 amNAS-MDW
13h 11m2 stops
$672
Find Deal
jue., oct. 9 - lun., oct. 13
WestJet Logo
5:04 pm - 3:21 pmMDW-SXM
20h 17m2 stops
WestJet Logo
4:20 pm - 10:59 amSXM-MDW
20h 39m2 stops
$3,259WestJet
Find Deal
mar., dic. 23 - lun., dic. 29
WestJet Logo
12:48 pm - 2:19 pmMDW-SXM
24h 31m2 stops
WestJet Logo
2:10 pm - 10:14 pmSXM-MDW
33h 04m2 stops
$3,261WestJet
Find Deal
mié., oct. 8 - dom., oct. 12

Frontier flights from Chicago Midway Airport to Caribbean Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier
Aug 30
MDW10:51 amChicago Midway
7h 27m
1 stop
SJU7:18 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU3:39 amSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
MDW9:51 amChicago Midway
$235
Find similar
Frontier
Sep 6
MDW10:51 amChicago Midway
12h 08m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
Sep 19
SJU3:39 amSan Juan Luis Munoz Marin Intl
7h 12m
1 stop
MDW9:51 amChicago Midway
$238
Find similar
Frontier
Aug 30
MDW10:51 amChicago Midway
21h 08m
1 stop
SJU8:59 amSan Juan Luis Munoz Marin Intl
Sep 6
SJU4:42 pmSan Juan Luis Munoz Marin Intl
17h 36m
1 stop
MDW9:18 amChicago Midway
$239
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
Sep 1
MDW5:10 amChicago Midway
7h 55m
1 stop
PUJ2:05 pmPunta Cana
Sep 5
PUJ3:05 pmPunta Cana
7h 30m
1 stop
MDW9:35 pmChicago Midway
$343
Find similar
Southwest
Sep 6
MDW11:40 amChicago Midway
10h 00m
1 stop
SJU10:40 pmSan Juan Luis Munoz Marin Intl
Sep 13
SJU7:45 amSan Juan Luis Munoz Marin Intl
8h 50m
2 stops
MDW3:35 pmChicago Midway
$351
Find similar
Southwest
Oct 9
MDW6:35 amChicago Midway
9h 05m
1 stop
SJU4:40 pmSan Juan Luis Munoz Marin Intl
Oct 13
SJU5:50 amSan Juan Luis Munoz Marin Intl
8h 30m
2 stops
MDW1:20 pmChicago Midway
$357
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 julio 31, 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

sáb. 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

vie. 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

sáb. 9/6

10:51 am-11:59 pm

1 stop12h 08m

San Juan Luis Munoz Marin Intl

vie. 9/19

3:39 am-9:51 am

1 stop7h 12m

$238

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

lun. 9/1

5:10 am-2:05 pm

1 stop7h 55m

Punta Cana

vie. 9/5

3:05 pm-9:35 pm

1 stop7h 30m

$343

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

sáb. 9/6

11:40 am-10:40 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

sáb. 9/13

7:45 am-3:35 pm

2 stops8h 50m

$351

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

dom. 10/26

6:00 am-2:31 pm

1 stop7h 31m

Punta Cana

dom. 11/2

4:56 pm-10:14 pm

1 stop7h 18m

$376

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 9/21

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

vie. 9/26

4:59 pm-12:28 pm

2 stops19h 29m

$389

ChicagoSaint Thomas Island

MDW - STT

MDWSTT

Chicago Midway

jue. 9/18

4:56 pm-9:44 am

2 stops15h 48m

Saint Thomas Island Cyril E King

dom. 9/21

10:49 am-11:20 pm

2 stops13h 31m

$586

ChicagoNassau

MDW - NAS

MDWNAS

Chicago Midway

jue. 10/9

8:39 am-4:25 pm

1 stop6h 46m

Nassau Intl

lun. 10/13

12:00 pm-12:11 am

2 stops13h 11m

$672

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mar. 12/23

5:04 pm-3:21 pm

2 stops20h 17m

Simpson Bay Princess Juliana

lun. 12/29

4:20 pm-10:59 am

2 stops20h 39m

$3,259

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 10/8

12:48 pm-2:19 pm

2 stops24h 31m

Simpson Bay Princess Juliana

dom. 10/12

2:10 pm-10:14 pm

2 stops33h 04m

$3,261

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 November is, on average, the cheapest month to fly to Caribbean Islands from Chicago Midway Airport, with most prices found around $318. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $328.

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 $456. 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 $456. 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 Punta Cana 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 $414 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 $304 on momondo.

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

There are 1 cabin classes 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

Best Price Found

$108

Fastest flight time

3h 55m

Direct flights

Sun

Airports in Caribbean Islands

10 airports
The best one-way flight to Caribbean Islands from Chicago Midway Airport in the past 72 hours is $108. The best round-trip flight deal from Chicago Midway Airport to Caribbean Islands found on momondo in the last 72 hours is $235.
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 3h 55m
Direct flights go from Chicago Midway Airport to Caribbean Islands on Sunday. The only airline offering direct flights is Southwest.
There are 10 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Santo Domingo Las Americas (SDQ), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), Simpson Bay Princess Juliana (SXM), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)
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  • 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 $133Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $149Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
DeltaPriceFrom $325Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $352Free CancellationRating
8.0
4,246 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.

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