$116+ Cheap flights from Midway (MDW) to Caribbean Islands
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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Midway to Caribbean Islands 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 Islands
Keep the following information in mind while searching for Midway to Caribbean Islands flight deals. Data was last updated June 18, 2025.
Round-trip from | $221 (Priceline) |
|---|---|
One-way from | $116 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $413 |
Find flight deals from Midway to Caribbean Islands
Cheapest flights from Midway to Caribbean IslandsExplore the most affordable flight options available from Midway to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.
Explore the most affordable flight options available from Midway to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.
This Priceline deal was found by Cheapflights users on 6/16. 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 6/16. 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 Southwest deal was found by Cheapflights users on 6/16. 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 Delta deal was found by Cheapflights users on 6/17. 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 6/16. 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 Priceline deal was found by Cheapflights users on 6/17. 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 6/17. 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 Booking.com deal was found by Cheapflights users on 6/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 6/17. 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 Booking.com 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 6/17. 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 6/16. 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 6/15. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated June 18, 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
Sun 6/29
9:12 pm-12:28 am
1 stop26h 16m
San Juan Luis Munoz Marin Intl
Fri 7/4
10:59 am-11:51 pm
1 stop13h 52m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Mon 9/22
6:35 am-1:55 pm
1 stop6h 20m
Punta Cana
Fri 9/26
3:05 pm-10:00 pm
1 stop7h 55m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 7/7
5:15 pm-12:55 am
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Fri 7/11
11:25 am-7:20 pm
2 stops8h 55m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sat 8/9
6:00 am-2:51 pm
1 stop7h 51m
Punta Cana
Thu 8/14
2:40 pm-9:49 pm
1 stop8h 09m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 8/12
6:04 am-4:36 pm
1 stop9h 32m
San Juan Luis Munoz Marin Intl
Sat 8/16
7:30 am-3:28 pm
1 stop8h 58m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Fri 7/11
6:40 pm-10:55 am
1 stop15h 15m
Punta Cana
Mon 7/14
11:20 am-11:51 pm
1 stop13h 31m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sun 9/14
6:00 am-3:33 pm
1 stop9h 33m
Montego Bay Sangster Intl
Wed 9/24
1:12 pm-9:44 pm
1 stop8h 32m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Sat 6/28
6:20 am-2:43 pm
1 stop8h 23m
Montego Bay Sangster Intl
Wed 7/2
9:18 am-1:49 pm
1 stop28h 31m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Thu 7/3
2:55 pm-12:19 am
1 stop8h 24m
Santo Domingo Las Americas
Sun 7/6
1:48 am-11:17 pm
1 stop22h 29m
ChicagoOranjestad
MDW - AUA
MDWAUA
Chicago Midway
Sat 7/26
6:20 am-2:29 pm
1 stop7h 09m
Oranjestad Reina Beatrix
Sat 8/2
3:35 pm-10:35 pm
1 stop8h 00m
Best time to book a flight from Midway to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Midway with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Caribbean Islands
What is the cheapest month to book a flight from Chicago Midway Airport to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Caribbean Islands (average of $254). Flying from Chicago Midway Airport to Caribbean Islands 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 EPX?
Find hourly flight availability from Midway to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 18, 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 Islands as you normally would.
Rainfall in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.
Temperature in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean Islands, 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 Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated June 18, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Air Transat from Chicago to Caribbean Islands to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Entertainment
Food
Overall
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Boarding
Entertainment
Food
Overall
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Boarding
Entertainment
Food
Overall
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Boarding
Entertainment
Food
Overall
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Boarding
Entertainment
Food
Overall
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Boarding
Entertainment
Food
Overall
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Midway to Caribbean Islands. 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 Islands
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Midway to Caribbean Islands
Discover the top 5 airlines that operate flights from Midway to Caribbean Islands. 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 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$368 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$309 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$299 | Average$443 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$325 | Average$661 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$354 | Average$686 | FlexibilityNo cancel fee | On-time63% |