$114 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 10/17. 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.
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1 adult, Economy

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Cheap Flights from Midway to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla1 stop$278
Aguadilla
Aguadilla1 stop$278

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

Fri, Oct 17 - Tue, Oct 21
Southwest Logo
5:50 pm - 9:50 amMDW-SJU
15h 00m2 stops
Southwest Logo
2:45 pm - 10:45 pmSJU-MDW
9h 00m1 stop
$227Southwest
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
1:37 pm - 2:19 pmMDW-SJU
23h 42m1 stop
Frontier Logo
4:24 pm - 11:38 amSJU-MDW
21h 14m1 stop
$233Frontier
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Fri, Nov 14 - Sun, Nov 16
Frontier Logo
9:15 am - 12:41 amMDW-SJU
13h 26m1 stop
Frontier Logo
2:11 am - 2:33 pmSJU-MDW
14h 22m1 stop
$237Frontier
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Thu, Oct 30 - Sun, Nov 2
Frontier Logo
9:15 am - 12:29 amMDW-SJU
14h 14m1 stop
Frontier Logo
2:03 am - 2:33 pmSJU-MDW
14h 30m1 stop
$240Frontier
Find Deal
Thu, Oct 23 - Wed, Oct 29
Frontier Logo
8:25 am - 12:29 amMDW-SJU
15h 04m1 stop
Frontier Logo
1:59 am - 2:33 pmSJU-MDW
13h 34m1 stop
$243Frontier
Find Deal
Mon, Oct 20 - Sat, Oct 25
Frontier Logo
10:33 am - 7:56 pmMDW-SJU
8h 23m1 stop
Frontier Logo
6:22 am - 10:47 pmSJU-MDW
17h 25m2 stops
$244Frontier
Find Deal
Fri, Oct 17 - Sun, Oct 19
Frontier Logo
10:33 am - 7:56 pmMDW-SJU
8h 23m1 stop
Frontier Logo
5:30 am - 9:33 amSJU-MDW
29h 03m1 stop
$247Frontier
Find Deal
Sat, Sep 27 - Wed, Oct 1
Frontier Logo
6:15 am - 2:11 pmMDW-SJU
6h 56m1 stop
Frontier Logo
9:26 pm - 3:58 pmSJU-MDW
19h 32m2 stops
$251Frontier
Find Deal
Tue, Jan 27 - Wed, Feb 4
Delta Logo
10:35 am - 8:30 pmMDW-SJU
7h 55m1 stop
Delta Logo
7:30 am - 4:25 pmSJU-MDW
10h 55m1 stop
$267Delta
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Tue, Nov 11 - Fri, Nov 14
Southwest Logo
10:40 am - 10:05 pmMDW-SJU
9h 25m1 stop
Southwest Logo
6:40 am - 11:25 amSJU-MDW
6h 45m1 stop
$292Southwest
Find Deal
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 $658 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 $658.

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 November, when tickets cost $295 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $593 and $499 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Puerto Rico?

The average price of all round-trip flights from Chicago Midway Airport to Puerto Rico clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Puerto Rico, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.

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 2 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$114
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 23% 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.

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

    The cheapest time of day to fly to Puerto Rico is generally at night, when round-trip flights cost $324 on average. Morning departures are around 42% more expensive than evening flights, 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 $510.

Reviews of the top 5 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 4242 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

No Tumberlence smooth flight. Try to change the menu on Snacks.

It was a good an early bird pleasant and quiet

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The spirit flight was on time. The airplane itself was surprisingly very nice. We had great seats. Seems like there's more room. Only complaint is that I didn't get a full refund for my mistakenly buying the baggage twice.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Everything you need to know for your flight from Midway to Puerto Rico

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