Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Caribbean Islands from $94

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 3/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
Multiple Airlines Logo
11:52 am - 1:56 pm
SJU
-
MDW
28h 04m
1 stop
$186Multiple Airlines
Sun, Mar 1 - Wed, Mar 4
Frontier Logo
9:22 pm - 12:43 am
MDW
-
SJU
25h 21m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$188Frontier
Mon, Mar 2 - Wed, Mar 4
Multiple Airlines Logo
2:19 pm - 6:58 pm
MDW
-
SJU
26h 39m
2 stops
Multiple Airlines Logo
6:50 pm - 1:41 pm
SJU
-
MDW
20h 51m
1 stop
$189Multiple Airlines
Mon, Mar 2 - Fri, Mar 6
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
Multiple Airlines Logo
11:52 am - 1:41 pm
SJU
-
MDW
27h 49m
1 stop
$191Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Frontier Logo
9:22 pm - 9:54 am
MDW
-
SJU
10h 32m
1 stop
Frontier Logo
5:25 pm - 2:26 pm
SJU
-
MDW
23h 01m
1 stop
$194Frontier
Mon, Feb 23 - Wed, Mar 4
Frontier Logo
8:00 am - 12:43 am
MDW
-
SJU
14h 43m
1 stop
Frontier Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
$197Frontier
Sat, Feb 28 - Thu, Mar 5
Southwest Logo
7:55 pm - 12:55 pm
MDW
-
GCM
16h 00m
2 stops
Southwest Logo
12:40 pm - 9:55 pm
GCM
-
MDW
9h 15m
2 stops
$364Southwest
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
9:15 pm - 2:55 pm
MDW
-
PLS
16h 40m
2 stops
Southwest Logo
3:50 pm - 7:35 am
PLS
-
MDW
16h 45m
2 stops
$368Southwest
Mon, Apr 27 - Tue, May 5
Delta Logo
6:00 am - 3:28 pm
MDW
-
MBJ
9h 28m
1 stop
Delta Logo
1:38 pm - 10:31 pm
MBJ
-
MDW
8h 53m
1 stop
$374Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
6:40 pm - 11:10 am
MDW
-
MBJ
15h 30m
1 stop
Delta Logo
2:42 pm - 8:50 am
MBJ
-
MDW
18h 08m
1 stop
$378Delta
Sun, Mar 1 - Wed, Apr 8

Frontier flights from Chicago Midway Airport to Caribbean Islands

Our best Frontier deals on Chicago Midway Airport to Caribbean Islands flight tickets
Frontier
Mar 2
MDW9:22 pmChicago Midway
25h 21m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
Mar 4
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$188
Frontier
Feb 23
MDW9:22 pmChicago Midway
10h 32m
1 stop
SJU9:54 amSan Juan Luis Munoz Marin Intl
Mar 4
SJU5:25 pmSan Juan Luis Munoz Marin Intl
23h 01m
1 stop
MDW2:26 pmChicago Midway
$194
Frontier
Feb 28
MDW8:00 amChicago Midway
14h 43m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
Mar 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 56m
1 stop
MDW1:56 pmChicago Midway
$197

Delta flights from Chicago Midway Airport to Caribbean Islands

Our best Delta deals on Chicago Midway Airport to Caribbean Islands flight tickets
Delta
Apr 21
MDW12:53 pmChicago Midway
6h 31m
1 stop
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Apr 25
SJU6:15 amSan Juan Luis Munoz Marin Intl
11h 14m
1 stop
MDW4:29 pmChicago Midway
$246
Delta
Feb 18
MDW12:45 pmChicago Midway
6h 27m
1 stop
SJU9:12 pmSan Juan Luis Munoz Marin Intl
Feb 26
SJU6:15 amSan Juan Luis Munoz Marin Intl
7h 44m
1 stop
MDW11:59 amChicago Midway
$284
Delta
Feb 18
MDW10:49 amChicago Midway
11h 09m
1 stop
SJU11:58 pmSan Juan Luis Munoz Marin Intl
Feb 25
SJU7:30 amSan Juan Luis Munoz Marin Intl
6h 29m
1 stop
MDW11:59 amChicago Midway
$286

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 February 8, 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

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 3/1

6:15 am-2:09 am

1 stop17h 54m

San Juan Luis Munoz Marin Intl

Wed 3/4

11:52 am-1:56 pm

1 stop28h 04m

$186

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

9:22 pm-12:43 am

1 stop25h 21m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:26 pm

1 stop23h 01m

$188

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 3/2

2:19 pm-6:58 pm

2 stops26h 39m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:50 pm-1:41 pm

1 stop20h 51m

$189

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 3/1

6:15 am-2:09 am

1 stop17h 54m

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-1:41 pm

1 stop27h 49m

$191

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

9:22 pm-9:54 am

1 stop10h 32m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:26 pm

1 stop23h 01m

$194

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/28

8:00 am-12:43 am

1 stop14h 43m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:00 am-1:56 pm

1 stop9h 56m

$197

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/3

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

Tue 3/10

12:40 pm-9:55 pm

2 stops9h 15m

$364

ChicagoProvidenciales

MDW - PLS

MDWPLS

Chicago Midway

Mon 4/27

9:15 pm-2:55 pm

2 stops16h 40m

Providenciales

Tue 5/5

3:50 pm-7:35 am

2 stops16h 45m

$368

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Tue 3/10

6:00 am-3:28 pm

1 stop9h 28m

Montego Bay Sangster Intl

Tue 3/17

1:38 pm-10:31 pm

1 stop8h 53m

$374

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:40 pm-11:10 am

1 stop15h 30m

Montego Bay Sangster Intl

Wed 4/8

2:42 pm-8:50 am

1 stop18h 08m

$378

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $330. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Chicago Midway Airport averaging around $331.

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 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 $402 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 $286 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 45m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Chicago Midway Airport to Caribbean Islands takes 3h 45m
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).
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
DeltaPriceFrom $132Free CancellationRating
7.9
8,172 reviews
Search Delta flights
FrontierPriceFrom $138Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
SouthwestPriceFrom $379Free CancellationRating
8.0
4,280 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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 3/10
Tue 3/17
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Londonfrom $344
Flights to Bangkokfrom $508
Flights to Tokyofrom $397
Flights to Los Angelesfrom $49
Flights to Parisfrom $304
Flights to Copenhagenfrom $372
Flights to Istanbulfrom $477
Flights to Manilafrom $498
Flights to Romefrom $342
Flights to Miamifrom $27
Flights to Chicagofrom $50