$100+ Cheap flights from Midway (MDW) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJU
Jan 11 — Jan 181
1 adult, Economy
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Cheapest flights from Midway to CaribbeanExplore the most affordable flight options available from Midway to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.
Explore the most affordable flight options available from Midway to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.
This CheapOair deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/153:10 pmMDW - SJU
1 stop9h 40mFrontier
Mon 12/224:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 12/10![Frontier logo]()
$246
This Frontier deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/142:59 pmMDW - SJU
1 stop6h 51mFrontier
Mon 12/224:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 12/11![Frontier logo]()
$259
This Priceline deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - SJU
1 stop18h 16mFrontier
Thu 12/186:00 amSJU - MDW
1 stop17h 58mFrontier
Deal found 12/10![Frontier logo]()
$263
This CheapOair deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/153:10 pmMDW - SJU
1 stop9h 40mFrontier
Fri 12/195:09 pmSJU - MDW
1 stop29h 55mFrontier
Deal found 12/11![Frontier logo]()
$271
This CheapOair deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:10 pmMDW - SJU
1 stop20h 24mFrontier
Thu 1/89:23 pmSJU - MDW
1 stop27h 46mFrontier
Deal found 12/10![Frontier logo]()
$285
This CheapOair deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:32 pmMDW - SJU
1 stop9h 07mFrontier
Thu 1/89:23 pmSJU - MDW
1 stop27h 46mFrontier
Deal found 12/11![Frontier logo]()
$289
This CheapOair deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 amMDW - SJU
1 stop24h 24mFrontier
Mon 12/294:21 pmSJU - MDW
1 stop7h 51mFrontier
Deal found 12/9![Frontier logo]()
$300
This CheapOair deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/142:59 pmMDW - SJU
1 stop6h 51mFrontier
Thu 12/1810:33 amSJU - MDW
1 stop13h 25mFrontier
Deal found 12/11![Frontier logo]()
$301
This CheapOair deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/112:16 pmMDW - SJU
1 stop18h 16mFrontier
Mon 12/154:31 pmSJU - MDW
1 stop7h 41mFrontier
Deal found 12/10![Frontier logo]()
$303
This CheapOair deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 amMDW - SJU
1 stop24h 24mFrontier
Fri 1/95:45 amSJU - MDW
1 stop10h 21mFrontier
Deal found 12/11![Frontier logo]()
$304
This Delta deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:00 amMDW - PUJ
1 stop6h 25mDelta
Wed 12/173:50 pmPUJ - MDW
1 stop9h 57mDelta
Deal found 12/10![Delta logo]()
$366
This CheapOair deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:12 amMDW - PUJ
1 stop6h 57mFrontier
Tue 12/3011:37 amPUJ - MDW
1 stop12h 35mFrontier
Deal found 12/10![Frontier logo]()
$380
Find flight deals from Midway to Caribbean
Keep the following information in mind while searching for Midway to Caribbean flight deals. Data was last updated December 12, 2025.
Round-trip from | $199 (Priceline) |
|---|---|
One-way from | $100 (Frontier) |
Popular in | December |
Cheapest in | April |
Average price | $592 |
Good round-trip deal | $381 or less |
Good one-way deal | $292 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Caribbean 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, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean that are best for you.
Fly from
Midway
Fly to
Caribbean
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 2/28
8:00 am-2:53 am
1 stop16h 53m
San Juan Luis Munoz Marin Intl
Sat 3/7
12:07 pm-11:32 pm
1 stop13h 25m
$201
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 2/6
1:00 pm-3:26 pm
1 stop24h 26m
San Juan Luis Munoz Marin Intl
Sat 2/14
8:02 pm-2:26 pm
1 stop20h 24m
$215
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/25
3:15 pm-12:40 am
1 stop7h 25m
San Juan Luis Munoz Marin Intl
Fri 1/30
6:10 am-11:35 am
1 stop7h 25m
$225
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 2/19
6:15 am-12:39 pm
1 stop28h 24m
San Juan Luis Munoz Marin Intl
Sun 2/22
3:53 am-8:32 pm
1 stop18h 39m
$231
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sat 2/14
6:00 am-3:20 pm
1 stop7h 20m
Simpson Bay Princess Juliana
Sat 2/28
4:30 pm-11:25 pm
1 stop8h 55m
$308
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
$310
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
$310
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/24
9:45 am-9:30 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Thu 2/26
5:30 am-1:30 pm
2 stops10h 00m
$320
ChicagoSaint Thomas Island
MDW - STT
MDWSTT
Chicago Midway
Sun 1/11
4:21 pm-2:52 pm
1 stop20h 31m
Saint Thomas Island Cyril E King
Thu 1/15
3:57 pm-9:09 am
1 stop19h 12m
$324
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 12/15
7:10 am-9:30 pm
1 stop12h 20m
San Juan Luis Munoz Marin Intl
Wed 12/17
8:55 am-4:35 pm
1 stop9h 40m
$325
Showing 1-10 of 60 results
Best time to book a flight from Midway to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Caribbean
What is the cheapest month to book a flight from Chicago Midway Airport to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $131). Flying from Chicago Midway Airport to Caribbean in June is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to CB?
Find hourly flight availability from Midway to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.
It’s typically best to fly out from Chicago Midway Airport to Caribbean in the evening. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.
What is the cheapest day to fly from Chicago Midway Airport to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Midway to Caribbean. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago Midway Airport to Caribbean flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated December 12, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Spirit Airlines from Chicago Midway Airport to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Midway to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Midway to Caribbean
Discover the top 4 airlines that operate flights from Midway to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$375 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$271 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$325 | Average$665 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$381 | Average$688 | FlexibilityNo cancel fee | On-time63% |