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Find cheap flights from Chicago Midway Airport to Puerto Rico from $135

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 6/4. 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
0 bags
jue. 6/27
jue. 7/4

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Best Puerto Rico Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Aguadilla
Aguadilla1 stop$292

Good to know

Low season

April

High season

December

Cheapest flight

$135
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 27% increase in price.
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 to Puerto Rico 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 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 to Puerto Rico with an airline and back to Chicago Midway Airport 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 to Puerto Rico from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Puerto Rico

  • Morning departure is around 9% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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
DeltaOverall score based on 10502 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
8.6Crew
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Didn’t happen. They stranded us in Orlando and had to book a flight on frontier to get to our destination.

Flight was delayed 2+ hours missed a concert because of it…

Flight left very close to original projected time. Paid for checked bag weight overage (my fault). Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

Flight left very close to original projected time. Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

I particularly did not have no problem with my backpack, but a few people in front of me did. The chairs were really uncomfortable. Unless is a super short flight for over a weekend I wouldn't take this airline.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Book cheap flights from Chicago to Puerto Rico

Recent round-trip flight deals

9/16lun.
1 stopFrontier
10h 47mMDW-SJU
10/3jue.
1 stopFrontier
13h 08mSJU-MDW
$258
9/5jue.
1 stopFrontier
10h 47mMDW-SJU
9/9lun.
1 stopFrontier
13h 08mSJU-MDW
$264
9/20vie.
1 stopFrontier
10h 47mMDW-SJU
10/5sáb.
1 stopFrontier
13h 37mSJU-MDW
$268
6/8sáb.
1 stopFrontier
16h 37mMDW-SJU
6/12mié.
1 stopFrontier
7h 23mSJU-MDW
$270
8/30vie.
1 stopFrontier
8h 57mMDW-SJU
9/6vie.
1 stopFrontier
9h 44mSJU-MDW
$274
6/7vie.
1 stopFrontier
14h 11mMDW-SJU
6/14vie.
1 stopFrontier
12h 58mSJU-MDW
$276
8/26lun.
1 stopDelta
8h 32mMDW-SJU
8/28mié.
1 stopDelta
9h 50mSJU-MDW
$359
10/19sáb.
1 stopDelta
10h 52mMDW-SJU
10/27dom.
1 stopDelta
8h 19mSJU-MDW
$419
9/2lun.
1 stopDelta
8h 32mMDW-SJU
9/8dom.
1 stopDelta
8h 27mSJU-MDW
$443
7/1lun.
2 stops
10h 31mMDW-SJU
7/8lun.
2 stops
16h 27mSJU-MDW
$492

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Recent one-way flight deals

6/4mar.
1 stopFrontier
12h 38mMDW-SJU
$135
6/19mié.
1 stopFrontier
17h 41mMDW-SJU
$138
8/23vie.
1 stopFrontier
8h 57mMDW-SJU
$139
8/7mié.
1 stopFrontier
16h 41mMDW-SJU
$140
6/16dom.
1 stopFrontier
16h 43mMDW-SJU
$143
6/7vie.
2 stops
16h 51mMDW-SJU
$152
10/31jue.
1 stopDelta
6h 27mMDW-SJU
$172
6/7vie.
2 stops
10h 07mMDW-SJU
$195
6/14vie.
1 stopAvelo Airlines
13h 45mMDW-SJU
$427
10/11vie.
1 stopDelta
6h 27mMDW-SJU
$1,247

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Last minute flights from Midway to Puerto Rico

Last minute flight, train and bus deals

5/30jue.
multi-stopFrontier
8h 31mMDW-SJU
6/5mié.
multi-stopFrontier
7h 23mSJU-MDW
$289
6/1sáb.
multi-stopFrontier
8h 24mMDW-SJU
6/4mar.
multi-stopFrontier
13h 28mSJU-MDW
$295
6/2dom.
multi-stopFrontier
13h 59mMDW-SJU
6/8sáb.
multi-stopFrontier
14h 26mSJU-MDW
$296
5/30jue.
multi-stopFrontier
8h 31mMDW-SJU
6/6jue.
multi-stopFrontier
11h 26mSJU-MDW
$297
6/1sáb.
multi-stopFrontier
8h 24mMDW-SJU
6/7vie.
multi-stopFrontier
12h 45mSJU-MDW
$298
5/29mié.
multi-stopFrontier
9h 13mMDW-SJU
6/2dom.
multi-stopFrontier
21h 08mSJU-MDW
$303
6/1sáb.
multi-stopFrontier
14h 05mMDW-SJU
6/8sáb.
multi-stopFrontier
19h 45mSJU-MDW
$308
6/1sáb.
multi-stopFrontier
8h 24mMDW-SJU
6/3lun.
multi-stopFrontier
9h 22mSJU-MDW
$309
5/31vie.
multi-stop
35h 43mMDW-SJU
6/6jue.
multi-stop
17h 11mSJU-MDW
$523
5/31vie.
multi-stop
15h 25mMDW-SJU
6/2dom.
multi-stop
21h 36mSJU-MDW
$544

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Chicago Midway Airport - Puerto Rico Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Puerto Rico - Chicago Midway Airport

Cabin classes:

$59

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