$134 Cheap Flights from Chicago (MDW) to San Juan (SJU)

View $134 flight on Tue, Nov 18, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)

Cheap Flights from Chicago to San Juan (MDW-SJU)

Prices were available within the past 7 days and start at $134 for one-way flights and $215 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Sep 15 - Sun, Sep 28
MDW
Chicago
SJU
San Juan
$215 Roundtrip, found 4 days ago
$215
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Chicago to San Juan, returning Sun, Sep 28, priced at $215 found 4 days ago
Frontier Airlines
Mon, Oct 27 - Sun, Nov 2
MDW
Chicago
SJU
San Juan
$225 Roundtrip, found 11 hours ago
$225
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Oct 27 from Chicago to San Juan, returning Sun, Nov 2, priced at $225 found 11 hours ago
Frontier Airlines
Sat, Oct 25 - Sun, Nov 2
MDW
Chicago
SJU
San Juan
$228 Roundtrip, found 4 days ago
$228
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to San Juan, returning Sun, Nov 2, priced at $228 found 4 days ago
Frontier Airlines
Sun, Sep 21 - Sat, Sep 27
MDW
Chicago
SJU
San Juan
$234 Roundtrip, found 12 hours ago
$234
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Sep 21 from Chicago to San Juan, returning Sat, Sep 27, priced at $234 found 12 hours ago
Frontier Airlines
Thu, Nov 6 - Mon, Nov 10
MDW
Chicago
SJU
San Juan
$235 Roundtrip, found 10 hours ago
$235
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Chicago to San Juan, returning Mon, Nov 10, priced at $235 found 10 hours ago
Frontier Airlines
Sat, Sep 20 - Sat, Sep 27
MDW
Chicago
SJU
San Juan
$237 Roundtrip, found 20 hours ago
$237
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Sep 20 from Chicago to San Juan, returning Sat, Sep 27, priced at $237 found 20 hours ago
Frontier Airlines
Mon, Sep 22 - Sat, Sep 27
MDW
Chicago
SJU
San Juan
$238 Roundtrip, found 23 hours ago
$238
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Sep 22 from Chicago to San Juan, returning Sat, Sep 27, priced at $238 found 23 hours ago
Frontier Airlines
Thu, Oct 30 - Sun, Nov 2
MDW
Chicago
SJU
San Juan
$238 Roundtrip, found 1 hour ago
$238
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Chicago to San Juan, returning Sun, Nov 2, priced at $238 found 1 hour ago
Southwest Airlines
Tue, Nov 4 - Wed, Nov 5
MDW
Chicago
SJU
San Juan
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Chicago to San Juan, returning Wed, Nov 5, priced at $278 found 1 day ago
Delta
Tue, Dec 16 - Tue, Dec 30
MDW
Chicago
SJU
San Juan
$391 Roundtrip, just found
$391
Roundtrip
just found
Select Delta flight, departing Tue, Dec 16 from Chicago to San Juan, returning Tue, Dec 30, priced at $391 just found

Find the cheapest month to fly from Chicago (MDW) to San Juan (SJU)

November is typically the cheapest month to fly

From $138 - $639 per traveler.

Graph displaying average flight prices per month

Alternative airports near San Juan

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Luis Munoz Marin Intl. SJU. Cheapest option available. Average driving time to city center is 16 minutes. Flights from $304
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city center16 min
Flights from $304
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
$214
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 $134 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?
Secure a cheap one-way flight from $134 or cheap return flight from $215 from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
The cheapest month to fly from MDW to SJU is September, when demand is low. Off-peak season is often when airlines offer lower prices between these airports.
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 Midway Intl. Airport (MDW) to Luis Munoz Marin Intl. Airport (SJU)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest MDW to SJU flight.
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.

Explore a world of travel with Expedia

*Available to One Key members.