$74 Cheap Flights from Chicago (MDW) to San Juan (SJU)

View $74 flight on Mon, Jan 26, 2026Opens 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 $74 for one-way flights and $138 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jan 24 - Sat, Jan 31
MDW
Chicago
SJU
San Juan
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Chicago to San Juan, returning Sat, Jan 31, priced at $138 found 1 day ago
Frontier Airlines
Wed, Jan 7 - Thu, Jan 15
MDW
Chicago
SJU
San Juan
$148 Roundtrip, found 1 hour ago
$148
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Jan 7 from Chicago to San Juan, returning Thu, Jan 15, priced at $148 found 1 hour ago
Frontier Airlines
Fri, Jan 30 - Thu, Feb 5
MDW
Chicago
SJU
San Juan
$155 Roundtrip, found 18 hours ago
$155
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Jan 30 from Chicago to San Juan, returning Thu, Feb 5, priced at $155 found 18 hours ago
Frontier Airlines
Thu, Dec 4 - Thu, Jan 15
MDW
Chicago
SJU
San Juan
$155 Roundtrip, found 2 hours ago
$155
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Chicago to San Juan, returning Thu, Jan 15, priced at $155 found 2 hours ago
Frontier Airlines
Wed, Nov 19 - Thu, Dec 4
MDW
Chicago
SJU
San Juan
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Nov 19 from Chicago to San Juan, returning Thu, Dec 4, priced at $161 found 4 days ago
Frontier Airlines
Wed, Jan 7 - Sat, Jan 31
MDW
Chicago
SJU
San Juan
$163 Roundtrip, found 4 days ago
$163
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Jan 7 from Chicago to San Juan, returning Sat, Jan 31, priced at $163 found 4 days ago
Frontier Airlines
Fri, Feb 6 - Thu, Feb 12
MDW
Chicago
SJU
San Juan
$170 Roundtrip, found 1 hour ago
$170
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Feb 6 from Chicago to San Juan, returning Thu, Feb 12, priced at $170 found 1 hour ago
Frontier Airlines
Mon, Feb 9 - Fri, Feb 27
MDW
Chicago
SJU
San Juan
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Feb 9 from Chicago to San Juan, returning Fri, Feb 27, priced at $170 found 3 days ago
Southwest Airlines
Thu, Feb 5 - Mon, Feb 9
MDW
Chicago
SJU
San Juan
$203 Roundtrip, just found
$203
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Feb 5 from Chicago to San Juan, returning Mon, Feb 9, priced at $203 just found
Delta
Mon, Jan 19 - Fri, Jan 23
MDW
Chicago
SJU
San Juan
$227 Roundtrip, just found
$227
Roundtrip
just found
Select Delta flight, departing Mon, Jan 19 from Chicago to San Juan, returning Fri, Jan 23, priced at $227 just found

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

February is typically the cheapest month to fly

From $154 - $639 per traveler.

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 $485
SJU
Luis Munoz Marin Intl.
Cheapest
Average driving time to city center16 min
Flights from $485

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 $74 or cheap return flight from $138 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 January, 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.

Travel information

Origin airport
Midway Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$138
Distance
2058 mi
Average flight time
4 hours 40 mins

Book with confidence

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 January. 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 $74 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.

 

Chicago to San Juan Flights

Explore a world of travel with Expedia

San Juan nearby Airports

Ponce

Chicago to Mercedita
$329.07

Culebra

Chicago to Benjamin Rivera Noriega
$837.90

Vieques

Chicago to Antonio Rivera Rodriguez
$907.90
Chicago nearby Airports

Chicago

O'Hare Intl. to San Juan
$136.16
*Available to One Key members.