$98 Find Cheap Flights from Chicago Midway Airport to Puerto Rico

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 Puerto Rico 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

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Flight Deals

Book Cheap Midway to Puerto Rico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Puerto Rico 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 Puerto Rico

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 Puerto Rico flights

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

What is the cheapest Chicago Midway Airport to Puerto Rico flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Puerto Rico from Chicago Midway Airport found in the last 72 hours was to San Juan, at $487 round-trip. The most popular route is from Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $487.

What is the cheapest time of day to fly to Puerto Rico?

The average price for all round-trip flights from Chicago Midway Airport to Puerto Rico depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Puerto Rico is generally in the morning, when round-trip flights cost $574 on average. The most expensive time of day to fly to Puerto Rico is generally in the morning, which is peak travel time and where the average cost of a ticket is $574.

What is the cheapest month to fly from Chicago Midway Airport to Puerto Rico?

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 Puerto Rico, 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 Puerto Rico is February, when tickets cost $271 (return) on average. On the other hand, the most expensive months are June and December, when 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 Puerto Rico?

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 Puerto Rico, 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 Puerto Rico, 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

FAQs - booking Puerto Rico flights

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

    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 Puerto Rico.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Puerto Rico 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 Puerto Rico?

    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 from Chicago Midway Airport to Puerto Rico with an airline and back with another airline.

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

    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 from Chicago Midway Airport to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Midway to Puerto Rico

 
Need help choosing which airline to fly with from Midway to Puerto Rico? 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
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
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 Puerto Rico

Information on your arrival and departure airports