$114+ 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 10/17. 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 August or November, booked 29 days in advance, depart on a Monday or Tuesday and return on a Tuesday
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 June 12, 2025.
Round-trip from | $212 (Priceline) |
|---|---|
One-way from | $114 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $461 |
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 June 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 June 12, 2025.
This Priceline 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 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 6/10. 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 6/12. 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 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 Midway to San Juan 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 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
Fri 8/29
2:05 pm-11:54 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
Fri 9/5
4:42 pm-11:56 am
1 stop20h 14m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 11/4
10:35 am-11:21 pm
1 stop10h 46m
San Juan Luis Munoz Marin Intl
Wed 11/12
3:30 pm-9:44 pm
1 stop8h 14m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 7/10
2:55 pm-11:15 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 7/15
3:45 pm-10:20 pm
1 stop7h 35m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 10/17
6:15 am-2:15 pm
1 stop7h 00m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/11
1:11 pm-3:30 pm
2 stops25h 19m
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 7/15
4:05 pm-11:55 pm
1 stop6h 50m
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 June 9, 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San Juan (average of $254). Flying from Chicago Midway Airport to San Juan in June is currently the most expensive (average of $339). 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 June 12, 2025.
It’s typically best to fly out from Chicago Midway Airport to San Juan in the evening. Doing so could potentially save you 34% on the flight price compared to flying in the morning, 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. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Rainfall in San Juan by month
Plan your trip to San Juan by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in San Juan 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 San Juan when rainfall is around 2.2 in.
Temperature in San Juan by month
Plan your trip to San Juan by taking into account the average temperature totals by month.
If weather is an important factor for your trip to San Juan, 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 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 June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and Frontier from Chicago to San Juan. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
Food
Boarding
Crew
Entertainment
Comfort
Overall
Reviews
John,May 2025
PVD - BNA
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 5 airlines flying from Midway to San Juan
Discover the top 5 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 June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$133 | Average$275 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$293 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$299 | Average$443 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$325 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$354 | Average$488 | FlexibilityNo cancel fee | On-time63% |