MDW - SJU

$98 Find Cheap Flights from Chicago Midway Airport to San Juan

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Juan departing on 4/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Juan Luis Munoz Marin Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$205
Typical prices: $253-$451
Frontier
Mon 4/27Thu 4/30
MDW - SJU • 1 stop
Cheapest non-stop
$437
Southwest
Sat 5/16Sat 5/23
MDW - SJU • Non-stop
Nonstop flights
Sat, Sun
You can fly direct with Southwest. Average duration is 4h 37m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $399 (round-trip)
Shortest trip • 6h 23m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 71% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Juan!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Juan that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Juan

Mon, Apr 27 - Thu, Apr 30
Frontier Logo
9:14 am - 9:54 am
MDW
-
SJU
23h 40m
1 stop
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
$205Frontier
Sun, Apr 12 - Sat, Apr 18
Frontier Logo
5:05 am - 11:18 am
MDW
-
SJU
29h 13m
1 stop
Frontier Logo
3:21 am - 8:04 am
SJU
-
MDW
29h 43m
1 stop
$211Frontier
Fri, Apr 17 - Fri, Apr 24
Frontier Logo
9:14 am - 9:54 am
MDW
-
SJU
23h 40m
1 stop
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
$214Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
6:00 am - 6:49 pm
MDW
-
SJU
11h 49m
1 stop
Frontier Logo
8:00 am - 4:00 pm
SJU
-
MDW
9h 00m
1 stop
$221Frontier
Mon, Apr 13 - Tue, Apr 14
Frontier Logo
6:30 am - 11:53 pm
MDW
-
SJU
16h 23m
1 stop
Frontier Logo
3:08 am - 8:04 am
SJU
-
MDW
29h 56m
1 stop
$222Frontier
Fri, Apr 3 - Thu, Apr 9
Frontier Logo
5:30 am - 1:26 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
9:01 am - 9:21 pm
SJU
-
MDW
13h 20m
1 stop
$226Frontier
Thu, Apr 23 - Tue, Apr 28
Frontier Logo
8:26 am - 2:01 am
MDW
-
SJU
16h 35m
1 stop
Frontier Logo
3:08 am - 7:21 am
SJU
-
MDW
29h 13m
1 stop
$229Frontier
Wed, Apr 8 - Sat, Apr 18
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
8:00 am - 4:00 pm
SJU
-
MDW
9h 00m
1 stop
$231Frontier
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
6:30 am - 9:33 pm
MDW
-
SJU
14h 03m
1 stop
Frontier Logo
8:00 am - 4:00 pm
SJU
-
MDW
9h 00m
1 stop
$232Frontier
Tue, Apr 7 - Fri, Apr 10
Frontier Logo
2:56 pm - 12:52 am
MDW
-
SJU
8h 56m
1 stop
Frontier Logo
3:16 am - 11:05 pm
SJU
-
MDW
20h 49m
1 stop
$236Frontier
Booking Insights

KAYAK's insights & trends for Midway to San Juan flights

Get data-powered insights and trends into flights from Midway to San Juan to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport departing in April.

What is the cheapest month to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport is February, where tickets cost $271 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $475 and $470 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$98
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Chicago Midway Airport to San Juan

When to book flights from Midway to San Juan

Are your dates flexible? Find out the best times to travel from Midway to San Juan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Juan flights

  • What is the cheapest flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport was $98 for a one-way ticket and $205 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Juan?

    A passport is required to fly from Chicago Midway Airport to San Juan.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Juan?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to San Juan flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Juan?

    The Airbus A321-100/200 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Juan flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to San Juan?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and San Juan.

  • On which days can I fly direct from Chicago Midway Airport to San Juan?

    You can catch a nonstop flight from Chicago Midway Airport to San Juan on Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to San Juan, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Southwest and Delta. With an average price for the route of $491 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $500 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Juan?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to San Juan.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Juan?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Juan from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to San Juan?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Juan with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJU can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Juan?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Juan from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago Midway Airport to San Juan?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Juan Luis Munoz Marin Intl.
Find which airlines fly direct from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Juan Luis Munoz Marin Intl

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago Midway

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top 3 airlines serving from Midway to San Juan

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Juan. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Juan? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4325 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Everything you need to know for your flight from Midway to San Juan

Information on your arrival and departure airports