$115+ Cheap flights from Caribbean to Midway (MDW)
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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Caribbean to Midway 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 Caribbean to Midway
Keep the following information in mind while searching for Caribbean to Midway flight deals. Data was last updated June 12, 2025.
Round-trip from | $203 (Priceline) |
|---|---|
One-way from | $115 (Frontier) |
Popular in | March |
Cheapest in | January |
Average price | $298 |
Good one-way deal | $232 or less |
Find flight deals from Caribbean to Midway
Cheapest flights from Caribbean to MidwayExplore the most affordable flight options available from Caribbean to Midway. 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 Caribbean to Midway. 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 6/12. 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 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 6/12. 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 Delta 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 6/11. 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.
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.
This SmartFares 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 SmartFares 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 Trip.com 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 Trip.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 6/10. 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 Booking.com 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 6/9. 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 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 6/10. 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.
This Southwest 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 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 Caribbean to Midway 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 Caribbean to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/11
1:11 am-7:20 am
1 stop7h 09m
Chicago Midway
Sun 9/21
8:15 am-11:58 pm
1 stop14h 43m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 6/26
6:30 am-1:15 pm
1 stop7h 45m
Chicago Midway
Wed 7/2
11:15 am-7:05 pm
1 stop6h 50m
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 9/11
12:55 pm-9:44 pm
1 stop9h 49m
Chicago Midway
Tue 9/16
10:35 am-10:08 pm
1 stop10h 33m
OranjestadChicago
AUA - MDW
AUAMDW
Oranjestad Reina Beatrix
Sat 8/2
3:35 pm-10:35 pm
1 stop8h 00m
Chicago Midway
Sat 8/9
6:20 am-2:29 pm
1 stop7h 09m
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Sun 6/15
9:18 am-11:18 pm
1 stop14h 00m
Chicago Midway
Sat 6/21
6:20 am-2:43 pm
1 stop8h 23m
Santo DomingoChicago
SDQ - MDW
SDQMDW
Santo Domingo Las Americas
Thu 10/9
3:11 pm-11:25 pm
1 stop9h 14m
Chicago Midway
Sun 10/19
6:15 am-1:51 pm
1 stop6h 36m
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Tue 7/15
3:24 pm-10:40 am
1 stop20h 16m
Chicago Midway
Tue 8/5
11:39 am-2:10 pm
1 stop25h 31m
Santo DomingoChicago
SDQ - MDW
SDQMDW
Santo Domingo Las Americas
Mon 10/27
7:00 am-6:36 pm
2 stops12h 36m
Chicago Midway
Thu 10/30
9:30 am-11:29 pm
2 stops12h 59m
Punta CanaChicago
PUJ - MDW
PUJMDW
Punta Cana
Tue 8/19
2:40 pm-9:49 pm
1 stop8h 09m
Chicago Midway
Tue 8/26
6:00 am-1:15 pm
1 stop6h 15m
Montego BayChicago
MBJ - MDW
MBJMDW
Montego Bay Sangster Intl
Wed 6/18
2:55 pm-11:45 pm
1 stop8h 50m
Chicago Midway
Mon 6/23
7:45 am-1:20 pm
1 stop5h 35m
Best time to book a flight from Caribbean to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Caribbean with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Chicago Midway Airport
What is the cheapest month to book a flight from Caribbean to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Caribbean to Chicago Midway Airport (average of $160). Flying from Caribbean to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 CB to MDW?
Find hourly flight availability from Caribbean to Midway. 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 Caribbean to Chicago Midway Airport as you normally would.
Rainfall in Midway by month
Plan your trip to Midway by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.
Temperature in Midway by month
Plan your trip to Midway by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated June 12, 2025.
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
John,May 2025
PVD - BNA
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Midway. 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 Caribbean to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Caribbean to Midway
Discover the top 3 airlines that operate flights from Caribbean to Midway. 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$148 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$527 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$332 | Average$332 | FlexibilityNo cancel fee | On-timeN/A |