$132+ 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 4/8. 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 March 28, 2025.
Round-trip from | $296 (Frontier) |
|---|---|
One-way from | $132 (Trip.com) |
Popular in | December |
Cheapest in | August |
Average price | $430 |
Good round-trip deal | $408 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 March 28, 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 March 28, 2025.
This Frontier deal was found by Cheapflights users on 3/27. 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 Delta deal was found by Cheapflights users on 3/27. 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 3/26. 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 3/27. 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 Kiwi.com deal was found by Cheapflights users on 3/27. 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 Kiwi.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 3/28. 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 Flightnetwork deal was found by Cheapflights users on 3/27. 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 Flightnetwork 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 3/27. 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 3/28. 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 CheapOair deal was found by Cheapflights users on 3/27. 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.
This Southwest deal was found by Cheapflights users on 3/27. 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 3/27. 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 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 March 28, 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 4/25
6:15 am-3:22 pm
1 stop8h 07m
San Juan Luis Munoz Marin Intl
Fri 5/2
6:00 am-5:28 pm
1 stop12h 28m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 4/20
6:04 am-1:15 pm
1 stop6h 11m
Punta Cana
Thu 4/24
12:55 pm-10:22 pm
1 stop10h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/26
6:04 am-2:19 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 5/3
3:34 pm-10:22 pm
1 stop7h 48m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 4/26
6:35 am-6:50 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Sat 5/3
1:00 pm-5:20 pm
Nonstop5h 20m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Sat 5/3
9:52 am-12:50 am
2 stops13h 58m
Santo Domingo Las Americas
Sat 5/10
7:05 am-9:14 pm
2 stops15h 09m
ChicagoPunta Cana
MDW - PUJ
MDWPUJ
Chicago Midway
Sun 5/11
8:30 am-1:34 pm
1 stop28h 04m
Punta Cana
Thu 5/15
2:59 pm-11:39 pm
1 stop9h 40m
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 5/30
9:12 pm-11:24 am
1 stop13h 12m
Simpson Bay Princess Juliana
Sat 6/14
12:36 pm-8:17 pm
1 stop8h 41m
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Mon 5/12
6:15 am-11:55 pm
2 stops16h 40m
Santo Domingo Las Americas
Mon 5/19
8:00 am-11:47 pm
2 stops16h 47m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Thu 5/1
6:30 pm-1:08 pm
1 stop18h 38m
Montego Bay Sangster Intl
Sun 5/4
2:28 pm-1:34 pm
1 stop23h 06m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 4/28
5:45 am-2:35 pm
1 stop8h 50m
Montego Bay Sangster Intl
Wed 5/7
12:35 pm-10:05 pm
1 stop9h 30m
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 December is currently the most expensive (average of $336). 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 March 28, 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 March 28, 2025.
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Crew
Boarding
Food
Entertainment
Comfort
Overall
Reviews
Ila,Mar 2025
HOU - DAL
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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 March 28, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$377 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$174 | Average$278 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$325 | Average$752 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$342 | Average$728 | FlexibilityNo cancel fee | On-time63% |