$114 Cheap Flights from Chicago (MDW) to San Juan (SJU)

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

Prices were available within the past 7 days and start at $114 for one-way flights and $153 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, May 10 - Sat, May 11
MDW
Chicago
SJU
San Juan
$153 Roundtrip, found 5 days ago
$153
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 10 from Chicago to San Juan, returning Sat, May 11, priced at $153 found 5 days ago
Frontier Airlines
Fri, May 10 - Sat, May 11
MDW
Chicago
SJU
San Juan
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 10 from Chicago to San Juan, returning Sat, May 11, priced at $191 found 5 days ago
Frontier Airlines
Sat, May 11 - Sun, May 12
MDW
Chicago
SJU
San Juan
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 11 from Chicago to San Juan, returning Sun, May 12, priced at $201 found 6 days ago
Frontier Airlines
Fri, May 10 - Sat, May 11
MDW
Chicago
SJU
San Juan
$213 Roundtrip, found 5 days ago
$213
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 10 from Chicago to San Juan, returning Sat, May 11, priced at $213 found 5 days ago
Frontier Airlines
Tue, May 14 - Wed, May 15
MDW
Chicago
SJU
San Juan
$223 Roundtrip, found 2 hours ago
$223
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, May 14 from Chicago to San Juan, returning Wed, May 15, priced at $223 found 2 hours ago
Frontier Airlines
Tue, May 14 - Tue, May 21
MDW
Chicago
SJU
San Juan
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, May 14 from Chicago to San Juan, returning Tue, May 21, priced at $228 just found
Frontier Airlines
Sat, May 18 - Sun, May 19
MDW
Chicago
SJU
San Juan
$233 Roundtrip, found 5 days ago
$233
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Chicago to San Juan, returning Sun, May 19, priced at $233 found 5 days ago
Frontier Airlines
Sun, May 12 - Thu, Jun 13
MDW
Chicago
SJU
San Juan
$234 Roundtrip, found 5 days ago
$234
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, May 12 from Chicago to San Juan, returning Thu, Jun 13, priced at $234 found 5 days ago
Frontier Airlines
Tue, May 14 - Tue, May 21
MDW
Chicago
SJU
San Juan
$236 Roundtrip, just found
$236
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, May 14 from Chicago to San Juan, returning Tue, May 21, priced at $236 just found
Frontier Airlines
Fri, May 17 - Fri, May 31
MDW
Chicago
SJU
San Juan
$238 Roundtrip, found 5 days ago
$238
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, May 17 from Chicago to San Juan, returning Fri, May 31, priced at $238 found 5 days ago
Flights from Chicago (MDW) to San Juan (SJU)
Origin airport
Midway Intl.
Destination airport
Luis Munoz Marin Intl.
Airlines serving
Delta, Frontier Airlines
Roundtrip price
$152
Distance
2058 mi
Average flight time
3 hours 40 mins

Chicago to San Juan Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to San Juan offer the perfect respite. Not only does exploring San Juan provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to San Juan may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of San Juan are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to San Juan more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to San Juan is $114 now!

Frequently asked questions

How much is a one-way flight from Chicago Airport to SJU?
Get set to snap up a bargain, because one-way Chicago flights to San Juan start from only $124. This is based on the cheapest price found on Expedia for this route departing within the next three months. This airfare is for an Frontier Airlines flight, departing from Midway Intl. Airport (MDW) on May 22 2024 and landing at SJU. The price was updated on May 1 2024 and has not changed since.
How long does it take to fly from Midway Intl. Airport (MDW) to Isla Verde Intl. Airport?
With Frontier Airlines, a direct flight takes approximately 4 hours and 39 minutes. Hop on the 10:31AM flight from Midway Intl. Airport (MDW) and reach Luis Munoz Marin Intl. Airport (SJU) at 4:10PM. Snap up a fantastic deal on this and many other routes when you purchase your ticket with Expedia.
Is it cheaper to buy a plane ticket from Midway Airport to SJU last minute?
Booking your trip from Midway Airport to Isla Verde Intl. Airport last minute could save you money if you’re lucky enough to find an amazing deal. However, fares don’t typically get cheaper closer to the departure date. If you choose to wait, flights could also be booked solid or the best seats taken. If you don’t want to hedge your bets, book well in advance of your departure date. It’s worth noting that some of the best deals can be found up to a year in advance. If your favorite airline hasn’t released tickets yet, check back regularly as offers are updated on Expedia constantly.
What is the cheapest airline flying from MDW to Isla Verde Intl. Airport in the next 90 days?
With ticket prices starting at $124 for a flight from Chicago to San Juan, Frontier Airlines is the cheapest airline found on Expedia. This price is based on airfares found on Expedia departing within the next 90 days and was updated on May 1 2024 and has not changed since. The flight jets off from Midway Intl. Airport (MDW) on May 22 2024 and arrives at SJU.
What's the cheapest price for a flight from MDW to Isla Verde Intl. Airport next month?
With a one-way flight from Chicago to San Juan on sale for $124, you’ll have more dough left over for awesome adventures. This airfare was found after searching through all available flights on Expedia within the next 30 days. This particular service sets off from Chicago Airport on May 22 2024, touches down at SJU and is operated by Frontier Airlines. The price of this flight was last updated on May 1 2024 and has not changed since.
What airports do you fly into for San Juan from Chicago?
From Chicago, you can journey to San Juan via Luis Munoz Marin Intl. Airport (SJU), Antonio Rivera Rodriguez Airport (VQS) and Mercedita Airport (PSE). Be sure to check which terminal is the most convenient for you before you make a decision. If you decide on Luis Munoz Marin Intl. Airport (SJU), it’s approximately 7 mi east of the city center. Use the dough you save when booking your seat with Expedia to visit the city’s popular attractions, such as San Juan Gate and La Fortaleza.
What are the most popular departure times for flights from MDW to Isla Verde Intl. Airport?
For Frontier Airlines flights heading from Midway Airport to Luis Munoz Marin Intl. Airport (SJU), the most popular departure times are between 10:00 AM - 11:00 AM. If you’d like to avoid any delays, travel in the morning. This way you’re more likely to dodge the heavy air traffic that builds up in the skyways in the afternoon.
Can I change the date of my flight from MDW to Luis Munoz Marin Intl. Airport (SJU)?
It’s a cinch to make changes to your Midway Airport to Luis Munoz Marin Intl. Airport (SJU) journey yourself. Just go to the Expedia Trips portal and choose “change flight.” Search for new flights and choose the one that fits your new plans. You’ll see an estimate of applicable flight change costs. You can also visit our Customer Service portal to chat to our Virtual Agent and get answers to all your questions.
Chicago nearby Airports

Chicago

O'Hare Intl. to San Juan
$107.56
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