$97+ 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 2/19. 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.Cheap 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 January 14, 2026.
Round-trip from | $199 (CheapOair) |
|---|---|
One-way from | $97 (Priceline) |
Popular in | July |
Cheapest in | May |
Average price | $357 |
Find 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 January 14, 2026.
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 January 14, 2026.
This CheapOair deal was found by Cheapflights users on 1/12. 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 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 1/13. 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 1/12. 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 CheapOair 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 1/13. 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 Priceline deal was found by Cheapflights users on 1/12. 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 Frontier deal was found by Cheapflights users on 1/12. 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 CheapOair deal was found by Cheapflights users on 1/12. 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 CheapOair 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 1/12. 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 CheapOair deal was found by Cheapflights users on 1/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Expedia deal was found by Cheapflights users on 1/11. 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 Expedia 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 1/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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
Mon 1/26
7:35 am-8:55 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Fri 1/30
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/19
9:50 am-10:25 pm
2 stops10h 35m
San Juan Luis Munoz Marin Intl
Fri 1/23
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/24
10:46 am-11:45 pm
1 stop10h 59m
San Juan Luis Munoz Marin Intl
Tue 1/27
3:55 pm-10:22 pm
1 stop8h 27m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 1/21
6:00 am-5:17 pm
1 stop9h 17m
San Juan Luis Munoz Marin Intl
Wed 1/28
7:30 am-11:59 am
1 stop6h 29m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 1/24
9:50 am-9:30 pm
2 stops9h 40m
San Juan Luis Munoz Marin Intl
Thu 1/29
6:10 am-1:55 pm
2 stops9h 45m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 1/19
6:00 am-2:31 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
Fri 1/23
6:09 am-11:59 am
1 stop7h 50m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/13
10:49 am-8:06 pm
1 stop8h 17m
San Juan Luis Munoz Marin Intl
Fri 4/17
6:15 am-4:36 pm
1 stop11h 21m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 4/10
9:15 pm-10:25 am
1 stop12h 10m
San Juan Luis Munoz Marin Intl
Tue 4/14
5:35 am-12:10 pm
1 stop7h 35m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 1/29
3:15 pm-12:35 am
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Mon 2/2
2:35 pm-10:05 pm
2 stops9h 30m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 1/27
9:50 am-7:05 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 1/31
3:00 pm-6:20 pm
Nonstop5h 20m
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 January 9, 2026.
The best time to book flights from Chicago Midway Airport to San Juan is 25 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 $137). 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 January 14, 2026.
When flying from Chicago Midway Airport to San Juan, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 January 14, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to San Juan, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Comfort
Overall
Crew
Boarding
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Entertainment
Comfort
Overall
Crew
Boarding
Food
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 3 airlines flying from Midway to San Juan
Discover the top 3 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 January 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$294 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$325 | Average$405 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$381 | Average$489 | FlexibilityNo cancel fee | On-time63% |