$118+ Cheap flights from Midway (MDW) to Puerto Rico
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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Midway to Puerto Rico 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
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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 Puerto Rico
Cheapest flights from Midway to Puerto RicoExplore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on dezembro 3, 2025.
Explore the most affordable flight options available from Midway to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on dezembro 3, 2025.
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Priceline deal was found by Cheapflights users on 12/1. 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 Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com deal was found by Cheapflights users on 12/1. 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 CheapOair deal was found by Cheapflights users on 12/3. 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 Kiwi.com deal was found by Cheapflights users on 12/2. 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 Kiwi.com deal was found by Cheapflights users on 12/1. 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 Frontier deal was found by Cheapflights users on 12/1. 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 12/1. 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 Frontier deal was found by Cheapflights users on 12/1. 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 12/2. 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 Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Find flight deals from Midway to Puerto Rico
Keep the following information in mind while searching for Midway to Puerto Rico flight deals. Data was last updated dezembro 3, 2025.
Round-trip from | $208 (Kiwi.com) |
|---|---|
One-way from | $118 (Kiwi.com) |
Popular in | December |
Cheapest in | April |
Average price | $567 |
Good one-way deal | $292 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Chicago Midway Airport to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 1/19
10:46 am-11:45 pm
1 stop10h 59m
San Juan Luis Munoz Marin Intl
sex 1/23
3:55 pm-10:22 pm
1 stop8h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 1/12
11:21 am-11:45 pm
1 stop10h 24m
San Juan Luis Munoz Marin Intl
sex 1/16
2:15 pm-10:07 pm
1 stop9h 52m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
ter 1/20
6:00 am-2:31 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
sex 1/23
3:55 pm-10:22 pm
1 stop8h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 1/26
9:50 am-11:10 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
ter 2/3
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 2/2
3:15 pm-12:35 am
1 stop7h 20m
San Juan Luis Munoz Marin Intl
sex 2/6
7:00 am-6:30 pm
1 stop13h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
ter 2/3
10:48 am-8:58 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
qui 2/5
7:30 am-11:59 am
1 stop6h 29m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
qui 2/19
6:10 am-9:50 pm
1 stop13h 40m
San Juan Luis Munoz Marin Intl
ter 2/24
9:05 am-2:45 pm
1 stop7h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
seg 2/9
1:35 pm-12:05 am
2 stops8h 30m
San Juan Luis Munoz Marin Intl
qua 2/18
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
ter 1/13
8:30 am-5:05 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
qua 1/21
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
qua 2/11
8:25 am-5:05 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
qua 2/18
9:05 am-6:35 pm
1 stop11h 30m
Best time to book a flight from Midway to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Midway with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Puerto Rico
What is the cheapest month to book a flight from Chicago Midway Airport to Puerto Rico?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Puerto Rico (average of $128). Flying from Chicago Midway Airport to Puerto Rico 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 PR?
Find hourly flight availability from Midway to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated dezembro 3, 2025.
Unlike at noon, when flights are generally more expensive, you can save up to 55% on flights from Chicago Midway Airport to Puerto Rico by exploring options for tickets in the evening.
What is the cheapest day to fly from Chicago Midway Airport to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Midway to Puerto Rico. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago Midway Airport to Puerto Rico 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.
How often are flights from Chicago to Puerto Rico delayed?
About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 96 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 22% of flights being delayed.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated dezembro 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Spirit Airlines from Chicago Midway Airport to Puerto Rico 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.
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Crew
Overall
Entertainment
Comfort
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to Puerto Rico. 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 Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Midway to Puerto Rico
Discover the top 4 airlines that operate flights from Midway to Puerto Rico. 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 dezembro 3, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$271 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$325 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$379 | Average$495 | FlexibilityNo cancel fee | On-time63% |