$142 Cheap Flights from Chicago (MDW) to San Juan (SJU)

View $142 flight on Thu, Sep 11, 2025Opens in a new window
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Cheap Flights from Chicago to San Juan (MDW-SJU)

Prices were available within the past 7 days and start at $142 for one-way flights and $302 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Sep 30 - Wed, Oct 1
MDW
Chicago
SJU
San Juan
$302 Roundtrip, found 1 day ago
$302
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 30 from Chicago to San Juan, returning Wed, Oct 1, priced at $302 found 1 day ago
Frontier Airlines
Thu, May 1 - Fri, May 2
MDW
Chicago
SJU
San Juan
$303 Roundtrip, found 1 hour ago
$303
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, May 1 from Chicago to San Juan, returning Fri, May 2, priced at $303 found 1 hour ago
Delta
Sat, Sep 27 - Wed, Oct 1
MDW
Chicago
SJU
San Juan
$307 Roundtrip, found 12 hours ago
$307
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, Sep 27 from Chicago to San Juan, returning Wed, Oct 1, priced at $307 found 12 hours ago
Frontier Airlines
Thu, May 8 - Sun, May 11
MDW
Chicago
SJU
San Juan
$308 Roundtrip, just found
$308
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to San Juan, returning Sun, May 11, priced at $308 just found
Frontier Airlines
Thu, May 8 - Fri, May 9
MDW
Chicago
SJU
San Juan
$313 Roundtrip, found 7 hours ago
$313
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to San Juan, returning Fri, May 9, priced at $313 found 7 hours ago
Frontier Airlines
Fri, May 9 - Wed, May 21
MDW
Chicago
SJU
San Juan
$318 Roundtrip, found 10 hours ago
$318
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, May 9 from Chicago to San Juan, returning Wed, May 21, priced at $318 found 10 hours ago
Frontier Airlines
Thu, May 8 - Sun, May 11
MDW
Chicago
SJU
San Juan
$318 Roundtrip, just found
$318
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, May 8 from Chicago to San Juan, returning Sun, May 11, priced at $318 just found
Frontier Airlines
Thu, Jun 5 - Fri, Jun 6
MDW
Chicago
SJU
San Juan
$323 Roundtrip, found 12 hours ago
$323
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Jun 5 from Chicago to San Juan, returning Fri, Jun 6, priced at $323 found 12 hours ago
Frontier Airlines
Sun, May 18 - Fri, May 23
MDW
Chicago
SJU
San Juan
$328 Roundtrip, found 8 hours ago
$328
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, May 18 from Chicago to San Juan, returning Fri, May 23, priced at $328 found 8 hours ago
Southwest Airlines
Thu, Sep 18 - Wed, Sep 24
MDW
Chicago
SJU
San Juan
$335 Roundtrip, found 3 hours ago
$335
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Chicago to San Juan, returning Wed, Sep 24, priced at $335 found 3 hours ago
Flights from Chicago (MDW) to San Juan (SJU)
Origin airport
Midway Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$301
Distance
2058 mi

Chicago to San Juan Flights

The cheapest times to fly from Chicago to San Juan

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Juan are during the month of September. You can find some of the cheapest flights from Chicago to San Juan with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to San Juan

Sunday is one of the best days to book for cheap flights from Chicago to San Juan: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to San Juan

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Juan in 2025. You can also book with separate airlines for your outbound and return journeys, from $142 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Juan flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Juan airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU) cost?
Book cheap return fares starting at $327 from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving MDW on May 3 2025 and touching down at SJU. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from MDW to SJU?
The cheapest flights from MDW to SJU are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
Jump on a nonstop flight with Southwest Airlines and go straight from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU).
What is the cheapest airline that flies from MDW to SJU?
With fares starting at $206 for a one-way flight from MDW to SJU, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on July 5 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
On average you can take your pick of 1 direct flights per week from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU). For greater flexibility, consider flights with layovers. Simply enter your details on Expedia and then filter your search to include one stop or more.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
The 8 AM departures from MDW to SJU see the highest demand. These flights can come with a higher price due to their popularity. If you want to save on your fare, choose a less crowded time to fly.
What day of the week has the most flights from MDW to SJU?
If you travel on a Saturday, you’ll get the widest range of choices for flights from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU).
What is the earliest flight from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
Midway Intl. Airport (MDW)’s first flight to Luis Munoz Marin Intl. Airport (SJU) is at approximately 8:55AM UTC-6. With a total travel time of 4h 35m, you’ll touch down at around 3:30PM UTC-4.
How long does it take to fly from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
The average flight time from MDW to SJU is 4 hours and 35 minutes, covering a total distance of 2,100 mi.
What airline has the least delays from MDW to SJU?
Consider booking with Southwest Airlines if you’d like to go straight from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU) without any delays. This airline has the best track record for punctuality, with an on-time performance of 100%. Want to be updated if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
Opt for a flight from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for San Juan from Midway Intl. Airport (MDW)?
If you’re on a direct flight from Midway Intl. Airport (MDW) to San Juan, Luis Munoz Marin Intl. Airport (SJU) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU) last-minute?
Holding off until just before your trip to book your flight from MDW to SJU often results in higher prices. While it’s possible to find some last-minute discounts, they aren’t always guaranteed. Allow some flexibility in your schedule for the best chance of snagging a bargain.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
If you reserved your MDW to SJU flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

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*Available to One Key members.