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MDW - SJU

$135 Find cheap flights from Chicago Midway Airport to San Juan

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 San Juan 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
qui 6/27
qui 7/4

Search hundreds of travel sites at once for deals on flights to San Juan

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to San Juan (MDW-SJU)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Juan 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 and deals for you by selecting your travel dates.
Choose your dates
10:00 am - 9:47 pmMDW-SJU
10h 47m1 stop
10:47 pm - 10:55 amSJU-MDW
13h 08m1 stop
$258Frontier
Find Deal
seg, set 16 - qui, out 3
10:00 am - 9:47 pmMDW-SJU
10h 47m1 stop
10:47 pm - 10:55 amSJU-MDW
13h 08m1 stop
$264Frontier
Find Deal
qui, set 5 - seg, set 9
10:00 am - 9:47 pmMDW-SJU
10h 47m1 stop
10:18 pm - 10:55 amSJU-MDW
13h 37m1 stop
$268Frontier
Find Deal
sex, set 20 - sáb, out 5
9:31 am - 3:08 amMDW-SJU
16h 37m1 stop
3:08 am - 9:31 amSJU-MDW
7h 23m1 stop
$270Frontier
Find Deal
sáb, jun 8 - qua, jun 12
3:28 pm - 1:25 amMDW-SJU
8h 57m1 stop
1:25 am - 10:09 amSJU-MDW
9h 44m1 stop
$274Frontier
Find Deal
sex, ago 30 - sex, set 6
2:32 pm - 5:43 amMDW-SJU
14h 11m1 stop
11:00 am - 10:58 pmSJU-MDW
12h 58m1 stop
$276Frontier
Find Deal
sex, jun 7 - sex, jun 14
12:35 pm - 10:07 pmMDW-SJU
8h 32m1 stop
12:56 pm - 9:46 pmSJU-MDW
9h 50m1 stop
$359Delta
Find Deal
seg, ago 26 - qua, ago 28
10:11 am - 10:03 pmMDW-SJU
10h 52m1 stop
2:25 pm - 9:44 pmSJU-MDW
8h 19m1 stop
$419Delta
Find Deal
sáb, out 19 - dom, out 27
12:35 pm - 10:07 pmMDW-SJU
8h 32m1 stop
7:30 am - 2:57 pmSJU-MDW
8h 27m1 stop
$443Delta
Find Deal
seg, set 2 - dom, set 8
2:14 pm - 1:45 amMDW-SJU
10h 31m2 stops
4:50 am - 8:17 pmSJU-MDW
16h 27m2 stops
seg, jul 1 - seg, jul 8

Flights from Midway to San Juan - Travel Insights & Trends

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

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Juan?

The average price of all flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport clicked on KAYAK for each day over the last 12 months.
When flying from Chicago Midway Airport to San Juan, you should consider leaving on a Sunday and avoid Thursdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, 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 San Juan Luis Munoz Marin Intl Airport is October, where tickets cost $242 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $511 and $411 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 56 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to San Juan?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago Midway Airport to San Juan were found on Frontier ($258) and Delta ($359). Frontier proposed the cheapest one-way flight at $135.

How many flights are there between Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in San Juan Luis Munoz Marin Intl Airport, with an average flight time of 4h 47m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 2 flights.

Which cabin class options are there for flights between Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Chicago Midway Airport to San Juan?

Early birds can take the earliest flight from Chicago Midway Airport at 8:05 am and will be landing in San Juan Luis Munoz Marin Intl Airport at 1:55 pm.

What’s the latest departure time from Chicago Midway Airport to San Juan?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport jets off at 8:35 am and lands at 2:20 pm.

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

When to book flights from Midway to San Juan

Are your dates flexible? Find out the best times to travel from Midway to San Juan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Juan flights

  • What is the cheapest flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport was $135 for a one-way ticket and $258 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Juan?

    A passport is required to fly from Chicago Midway Airport to San Juan.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Juan?

    American Airlines, and Delta offer inflight Wi-Fi service on the Chicago Midway Airport to San Juan flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Juan?

    The Airbus A320neo is the aircraft model that flies most regularly on the Chicago Midway Airport to San Juan flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Juan?

    You can catch a nonstop flight from Chicago Midway Airport to San Juan on Saturday, and Sunday.

  • Which is the best airline for flights from Chicago to San Juan, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Delta and Frontier. With an average price for the route of $754 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $247 and an overall rating of 6.2.

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

    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 San Juan.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Juan 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 San Juan?

    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 San Juan with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SJU can sometimes prove cheaper using this method.

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

    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 San Juan 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

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $63 or less one-way and $144 or less round-trip.

Prefer to fly non-stop from Chicago Midway Airport to San Juan?

Find which airlines fly direct from Midway to Luis Munoz Marin Intl, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to San Juan Luis Munoz Marin Intl

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

San Juan Luis Munoz Marin Intl to Chicago Midway

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Midway to San Juan

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Juan. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Juan? 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
7.9Comfort
8.0Entertainment
8.6Crew
8.2Boarding
7.4Food
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 San Juan

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Juan found on KAYAK in the last 72 hours.
6/4ter
1 stopFrontier
12h 38mMDW-SJU
$135
6/19qua
1 stopFrontier
17h 41mMDW-SJU
$138
8/23sex
1 stopFrontier
8h 57mMDW-SJU
$139
8/7qua
1 stopFrontier
16h 41mMDW-SJU
$140
6/16dom
1 stopFrontier
16h 43mMDW-SJU
$143
6/7sex
2 stops
16h 51mMDW-SJU
$152
10/31qui
1 stopDelta
6h 27mMDW-SJU
$172
6/7sex
2 stops
10h 07mMDW-SJU
$195
6/14sex
1 stopAvelo Airlines
13h 45mMDW-SJU
$427
10/11sex
1 stopDelta
6h 27mMDW-SJU
$1,247

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Last minute flights from Midway to San Juan

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San Juan that are departing in the next 10 days.
5/30qui
multi-stopFrontier
8h 31mMDW-SJU
6/5qua
multi-stopFrontier
7h 23mSJU-MDW
$289
6/1sáb
multi-stopFrontier
8h 24mMDW-SJU
6/4ter
multi-stopFrontier
13h 28mSJU-MDW
$295
6/2dom
multi-stopFrontier
13h 59mMDW-SJU
6/8sáb
multi-stopFrontier
14h 26mSJU-MDW
$296
5/30qui
multi-stopFrontier
8h 31mMDW-SJU
6/6qui
multi-stopFrontier
11h 26mSJU-MDW
$297
6/1sáb
multi-stopFrontier
8h 24mMDW-SJU
6/7sex
multi-stopFrontier
12h 45mSJU-MDW
$298
5/29qua
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
6/3seg
multi-stopFrontier
9h 22mSJU-MDW
$309
5/31sex
multi-stop
35h 43mMDW-SJU
6/6qui
multi-stop
17h 11mSJU-MDW
$523
5/31sex
multi-stop
15h 25mMDW-SJU
6/2dom
multi-stop
21h 36mSJU-MDW
$544

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Chicago Midway Airport - San Juan Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

San Juan (SJU)Puerto Rico

Return flight deals:

San Juan - Chicago Midway Airport

Cabin classes:

$59