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Find cheap flights from Chicago Midway Airport to Puerto Rico from $69

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 5/18. 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
Tue 6/4
Tue 6/11

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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$314

Good to know

Low season

April

High season

December

Cheapest flight

$69
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 26% 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 15% 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 10838 reviews
7.4Food
7.9Comfort
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

10.0 ExcellentBranton, May 2024AVL - ATL
Read more about Delta reviews

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

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.

Do I need to call them or will you handle my complaint ? I paid for one carry-on bag. my email said up to 50 pounds when I got to the counter they charged me $79 more for my 48 pound bag!!! they said nope only 40 pounds. My email says 50 pounds. !!! I’m out another $79!!!

Flight attendant very friendly. Seats not adjustable like before. I was in the middle seat and two big guys next to me isn’t to pleasant. No used to have delays in the past and now is too often.

Seats could use more padding. Kind of hard on the tush.

Amazed that Spirit can even get planes in the air, would never use again.

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to Puerto Rico

Recent round-trip flight deals

5/18Sat
1 stopFrontier
10h 15mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$137
5/21Tue
1 stopFrontier
12h 38mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$138
5/20Mon
1 stopFrontier
6h 28mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$139
5/19Sun
1 stopFrontier
12h 07mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$147
5/17Fri
1 stopFrontier
15h 38mMDW-SJU
5/18Sat
1 stopFrontier
9h 36mSJU-MDW
$173
5/14Tue
1 stopFrontier
11h 39mMDW-SJU
5/18Sat
1 stopFrontier
9h 36mSJU-MDW
$175
5/15Wed
1 stopFrontier
9h 38mMDW-SJU
5/18Sat
1 stopFrontier
9h 36mSJU-MDW
$176
5/16Thu
1 stopFrontier
17h 25mMDW-SJU
5/18Sat
1 stopFrontier
9h 36mSJU-MDW
$177
5/14Tue
1 stopFrontier
11h 39mMDW-SJU
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$188
5/18Sat
1 stopFrontier
8h 35mMDW-SJU
5/20Mon
1 stopFrontier
10h 03mSJU-MDW
$198

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Recent one-way flight deals

5/18Sat
1 stopFrontier
10h 15mMDW-SJU
$69
5/13Mon
1 stopFrontier
12h 17mMDW-SJU
$109
5/16Thu
1 stopFrontier
17h 25mMDW-SJU
$113
5/17Fri
1 stopFrontier
15h 38mMDW-SJU
$114
5/16Thu
1 stopFrontier
14h 03mMDW-SJU
$117
9/3Tue
1 stopFrontier
20h 11mMDW-SJU
$128
10/5Sat
1 stopFrontier
10h 18mMDW-SJU
$129
8/6Tue
1 stopFrontier
11h 34mMDW-SJU
$135
5/20Mon
3 stops
24h 28mMDW-SJU
$176
6/3Mon
2 stops
9h 41mMDW-SJU
$199

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Last minute flights from Midway to Puerto Rico

Last minute flight, train and bus deals

5/8Wed
multi-stopFrontier
12h 17mMDW-SJU
5/17Fri
multi-stopFrontier
10h 03mSJU-MDW
$278
5/7Tue
multi-stopFrontier
11h 39mMDW-SJU
5/17Fri
multi-stopFrontier
15h 48mSJU-MDW
$279
5/9Thu
multi-stopFrontier
7h 36mMDW-SJU
5/11Sat
multi-stopFrontier
14h 57mSJU-MDW
$280
5/8Wed
multi-stopFrontier
12h 31mMDW-SJU
5/16Thu
multi-stopFrontier
29h 30mSJU-MDW
$284
5/7Tue
multi-stopFrontier
12h 21mMDW-SJU
5/16Thu
multi-stopFrontier
29h 30mSJU-MDW
$285
5/8Wed
multi-stopFrontier
12h 17mMDW-SJU
5/14Tue
multi-stopFrontier
28h 46mSJU-MDW
$296
5/6Mon
multi-stop
10h 04mMDW-SJU
5/12Sun
multi-stop
23h 20mSJU-MDW
$698
5/5Sun
multi-stopDelta
6h 18mMDW-SJU
5/14Tue
multi-stopDelta
15h 01mSJU-MDW
$3,300
5/7Tue
multi-stopDelta
13h 20mMDW-SJU
5/14Tue
multi-stopDelta
9h 20mSJU-MDW
$3,957
5/8Wed
multi-stopDelta
11h 24mMDW-SJU
5/15Wed
multi-stopDelta
7h 06mSJU-MDW
$4,091

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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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