$117+ Cheap flights from Midway (MDW) to San Juan
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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Midway to San Juan 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.Cheapflights Tip: The best prices from Chicago Midway to San Juan are usually found in May or February, booked 29 days in advance, depart on a Monday or Tuesday and return on a Tuesday
Cheap flight deals from Midway to San Juan
Cheapest flights from Midway to San JuanExplore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.
Explore the most affordable flight options available from Midway to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.
This CheapOair deal was found by Cheapflights users on 12/10. 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 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 12/11. 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 Priceline deal was found by Cheapflights users on 12/10. 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 CheapOair deal was found by Cheapflights users on 12/11. 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 CheapOair 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 12/10. 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 CheapOair 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 12/11. 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 CheapOair 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 12/9. 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 CheapOair 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 12/11. 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 CheapOair 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 12/10. 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 CheapOair 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 12/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Find flight deals from Midway to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.
Round-trip from | $199 (Priceline) |
|---|---|
One-way from | $117 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $590 |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Chicago Midway Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 2/28
8:00 am-2:53 am
1 stop16h 53m
San Juan Luis Munoz Marin Intl
Sat 3/7
12:07 pm-11:32 pm
1 stop13h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 2/6
1:00 pm-3:26 pm
1 stop24h 26m
San Juan Luis Munoz Marin Intl
Sat 2/14
8:02 pm-2:26 pm
1 stop20h 24m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 1/25
3:15 pm-12:40 am
1 stop7h 25m
San Juan Luis Munoz Marin Intl
Fri 1/30
6:10 am-11:35 am
1 stop7h 25m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 2/19
6:15 am-12:39 pm
1 stop28h 24m
San Juan Luis Munoz Marin Intl
Sun 2/22
3:53 am-8:32 pm
1 stop18h 39m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/26
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:15 pm-10:22 pm
1 stop10h 07m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/24
9:45 am-9:30 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Thu 2/26
5:30 am-1:30 pm
2 stops10h 00m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 12/15
7:10 am-9:30 pm
1 stop12h 20m
San Juan Luis Munoz Marin Intl
Wed 12/17
8:55 am-4:35 pm
1 stop9h 40m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/28
1:50 pm-12:35 am
2 stops8h 45m
San Juan Luis Munoz Marin Intl
Tue 2/3
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 1/20
5:00 am-2:55 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 1/26
9:05 am-6:35 pm
1 stop11h 30m
Best time to book a flight from Midway to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Midway with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to San Juan
How far ahead should I book a flight from Chicago Midway Airport to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from Midway to San Juan. Price data was last updated on December 5, 2025.
The best time to book flights from Chicago Midway Airport to San Juan is 29 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago Midway Airport to San Juan?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $131). Flying from Chicago Midway Airport to San Juan 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 SJU?
Find hourly flight availability from Midway to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.
It’s typically best to fly out from Chicago Midway Airport to San Juan in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying at noon, which is usually more expensive.
What is the cheapest day to fly from Chicago Midway Airport to San Juan?
Use this chart to determine the cheapest time to fly round-trip from Midway to San Juan. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago Midway Airport to San Juan 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 San Juan delayed?
About 23% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 97 minutes.
What is the most punctual flight time for Chicago to San Juan 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 San Juan flights?
Over the last year, Southwest have had the lowest number of delays on this route, with just 23% of flights being delayed.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated December 12, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest, Delta, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Crew
Overall
Entertainment
Food
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Midway to San Juan. 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 San Juan
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Midway to San Juan
Discover the top 4 airlines that operate flights from Midway to San Juan. 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 December 12, 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$381 | Average$496 | FlexibilityNo cancel fee | On-time63% |