$93 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 8/23. 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

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Best Puerto Rico Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla1 stop$212
Aguadilla
Aguadilla1 stop$212

Cheap Flights from Midway to Puerto Rico

 
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

Sat, Aug 30 - Fri, Sep 5
Frontier Logo
10:51 am - 8:59 amMDW-SJU
21h 08m1 stop
Frontier Logo
3:40 am - 11:56 amSJU-MDW
9h 16m1 stop
$185Frontier
Find Deal
Sat, Oct 18 - Sun, Oct 26
Frontier Logo
11:21 am - 2:34 amMDW-SJU
14h 13m1 stop
Frontier Logo
9:07 am - 7:44 amSJU-MDW
23h 37m1 stop
$194Frontier
Find Deal
Thu, Oct 30 - Sat, Nov 1
Frontier Logo
6:15 am - 2:15 pmMDW-SJU
7h 00m1 stop
Frontier Logo
1:11 am - 8:20 amSJU-MDW
8h 09m1 stop
$203Frontier
Find Deal
Fri, Aug 29 - Thu, Sep 4
Frontier Logo
2:05 pm - 11:54 pmMDW-SJU
8h 49m1 stop
Frontier Logo
3:21 pm - 11:25 pmSJU-MDW
9h 04m1 stop
$212Frontier
Find Deal
Sat, Jul 12 - Sat, Jul 19
Frontier Logo
9:12 pm - 9:04 amMDW-SJU
10h 52m1 stop
Frontier Logo
3:08 pm - 10:35 pmSJU-MDW
8h 27m1 stop
$213Frontier
Find Deal
Tue, Nov 4 - Fri, Nov 14
Delta Logo
10:35 am - 11:21 pmMDW-SJU
10h 46m1 stop
Delta Logo
3:30 pm - 9:44 pmSJU-MDW
8h 14m1 stop
$331Delta
Find Deal
Thu, Jul 10 - Tue, Jul 15
Southwest Logo
2:55 pm - 11:15 pmMDW-SJU
7h 20m1 stop
Southwest Logo
3:45 pm - 10:20 pmSJU-MDW
7h 35m1 stop
$357Southwest
Find Deal
Fri, Aug 15 - Fri, Sep 12
Southwest Logo
1:45 pm - 11:30 pmMDW-SJU
8h 45m2 stops
Southwest Logo
5:50 am - 1:30 pmSJU-MDW
8h 40m2 stops
$361Southwest
Find Deal
Wed, Jul 16 - Wed, Jul 23
Southwest Logo
11:20 am - 11:25 pmMDW-SJU
11h 05m1 stop
Southwest Logo
7:30 am - 3:50 pmSJU-MDW
9h 20m1 stop
$364Southwest
Find Deal
Sat, Jul 26 - Thu, Jul 31
Southwest Logo
8:50 am - 2:35 pmMDW-SJU
4h 45mnonstop
Southwest Logo
5:50 pm - 1:05 amSJU-MDW
8h 15m1 stop
$375Southwest
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Puerto Rico.

The cheapest ticket to Puerto Rico from Chicago Midway Airport found in the last 72 hours was to San Juan, at $424 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 $424.

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 August, when tickets cost $307 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $599 and $500 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 seasonNovember
High seasonMay
Cheapest flight$93
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 20% 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 35% 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 $484.

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 4287 reviews
7.1Food
7.6Entertainment
8.2Boarding
8.0Comfort
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

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!!!

Amazing flying experience, even in not the best of weather. The staff made us comfortable and the flight was actually pretty smooth.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

It wasn’t a bad flight just very uncomfortable seating wise.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

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