$114+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Midway to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Caribbean
Keep the following information in mind while searching for Midway to Caribbean flight deals. Data was last updated June 12, 2025.
Round-trip from | $212 (Priceline) |
|---|---|
One-way from | $114 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $417 |
Good round-trip deal | $523 or less |
Good one-way deal | $238 or less |
Find flight deals from Midway to Caribbean
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 June 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 June 12, 2025.
This Priceline deal was found by Cheapflights users on 6/10. 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.
This Priceline deal was found by Cheapflights users on 6/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Priceline deal was found by Cheapflights users on 6/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/12. 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.
This Frontier deal was found by Cheapflights users on 6/12. 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.
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 June 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/29
2:05 pm-11:54 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
Fri 9/5
4:42 pm-11:56 am
1 stop20h 14m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 9/5
8:34 am-12:25 pm
1 stop26h 51m
Simpson Bay Princess Juliana
Sat 9/13
1:58 pm-7:39 am
1 stop18h 41m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 11/4
10:35 am-11:21 pm
1 stop10h 46m
San Juan Luis Munoz Marin Intl
Wed 11/12
3:30 pm-9:44 pm
1 stop8h 14m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Tue 9/2
6:00 am-2:34 pm
1 stop7h 34m
Punta Cana
Wed 9/24
2:42 pm-9:44 pm
1 stop8h 02m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 7/21
9:55 am-3:25 pm
Nonstop4h 30m
Punta Cana
Thu 7/24
4:05 pm-7:55 pm
Nonstop4h 50m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Thu 8/21
6:15 am-2:23 pm
1 stop7h 08m
Punta Cana
Sun 8/24
3:38 pm-11:27 pm
1 stop8h 49m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/10
2:55 pm-11:15 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 7/15
3:45 pm-10:20 pm
1 stop7h 35m
ChicagoOranjestad
MDW - AUA
MDWAUA
Chicago Midway
Sat 7/12
6:20 am-2:29 pm
1 stop7h 09m
Oranjestad Reina Beatrix
Sat 7/19
3:35 pm-10:35 pm
1 stop8h 00m
ChicagoSaint Thomas Island
MDW - STT
MDWSTT
Chicago Midway
Fri 7/18
10:31 am-9:48 am
2 stops22h 17m
Saint Thomas Island Cyril E King
Sun 7/20
4:05 pm-2:04 pm
2 stops22h 59m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 9/8
6:00 am-3:36 pm
1 stop9h 36m
Montego Bay Sangster Intl
Sat 9/13
2:23 pm-9:44 pm
1 stop7h 21m
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.
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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean (average of $254). Flying from Chicago Midway Airport to Caribbean in June is currently the most expensive (average of $339). 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 June 12, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Caribbean as you normally would.
Rainfall in Caribbean by month
Plan your trip to Caribbean by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.
Temperature in Caribbean by month
Plan your trip to Caribbean by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
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 June 12, 2025.
Boarding
Food
Crew
Comfort
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Boarding
Food
Crew
Comfort
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Boarding
Food
Crew
Comfort
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Boarding
Food
Crew
Comfort
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Boarding
Food
Crew
Comfort
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
Boarding
Food
Crew
Comfort
Overall
Entertainment
Reviews
John,May 2025
PVD - BNA
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.
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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 5 airlines flying from Midway to Caribbean
Discover the top 5 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$366 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$293 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$299 | Average$443 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$325 | Average$663 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$354 | Average$688 | FlexibilityNo cancel fee | On-time63% |