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MDW - SJU

Find cheap flights from Chicago Midway Airport to San Juan 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 San Juan departing on 5/9. 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
Sat 5/25
Sat 6/1

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 44,979,812 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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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
12:28 pm - 11:06 pmMDW-SJU
9h 38m1 stop
10:15 pm - 6:54 amSJU-MDW
9h 39m1 stop
$136Frontier
Find Deal
Wed, May 15 - Wed, May 22
10:37 am - 3:23 amMDW-SJU
15h 46m1 stop
6:48 am - 9:53 pmSJU-MDW
16h 05m1 stop
$137Frontier
Find Deal
Mon, May 13 - Wed, May 22
7:17 pm - 8:34 amMDW-SJU
12h 17m1 stop
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
$138Frontier
Find Deal
Mon, May 13 - Wed, May 15
2:44 pm - 3:23 amMDW-SJU
11h 39m1 stop
10:35 am - 12:46 amSJU-MDW
15h 11m1 stop
$140Frontier
Find Deal
Tue, May 14 - Thu, May 16
3:44 pm - 10:38 amMDW-SJU
17h 54m1 stop
3:08 am - 6:54 amSJU-MDW
28h 46m1 stop
$143Frontier
Find Deal
Mon, May 13 - Tue, May 14
10:37 am - 3:23 amMDW-SJU
15h 46m1 stop
8:33 pm - 12:09 amSJU-MDW
28h 36m1 stop
$146Frontier
Find Deal
Mon, May 13 - Fri, May 17
1:15 pm - 2:00 amMDW-SJU
11h 45m1 stop
6:48 am - 9:53 pmSJU-MDW
16h 05m1 stop
$147Frontier
Find Deal
Fri, May 17 - Wed, May 22
5:56 pm - 2:15 amMDW-SJU
7h 19m1 stop
2:50 am - 11:52 amSJU-MDW
10h 02m1 stop
$148Frontier
Find Deal
Thu, May 9 - Sat, May 11
8:17 pm - 1:56 amMDW-SJU
28h 39m1 stop
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
$155Frontier
Find Deal
Sat, May 11 - Wed, May 15
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
8:33 pm - 12:09 amSJU-MDW
28h 36m1 stop
$156Frontier
Find Deal
Sun, May 12 - Fri, May 17

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 Tuesday 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 Thursdays and the most expensive ones on Saturdays.

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 September, where tickets cost $238 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $556 and $523 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 70 days before departure.

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 40m. 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 8:50 am and will be landing in San Juan Luis Munoz Marin Intl Airport at 2:30 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 8:50 am and lands at 2:30 pm.

Good to know

Low season

April

High season

May

Cheapest flight

$69
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 9% lower on average.
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 $69 for a one-way ticket and $136 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.

  • 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

Top tips for finding a cheap flight from MDW to San Juan

  • 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 10975 reviews
7.4food
8.6crew
8.0entertainment
8.2boarding
7.9comfort
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

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.

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.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

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.
5/9Thu
1 stopFrontier
7h 19mMDW-SJU
$69
5/13Mon
1 stopFrontier
12h 17mMDW-SJU
$71
5/20Mon
1 stopFrontier
12h 21mMDW-SJU
$74
5/21Tue
1 stopFrontier
11h 49mMDW-SJU
$89
8/21Wed
1 stopFrontier
13h 20mMDW-SJU
$109
5/8Wed
1 stopFrontier
12h 31mMDW-SJU
$114
5/6Mon
1 stopFrontier
9h 38mMDW-SJU
$117
5/10Fri
1 stopFrontier
15h 46mMDW-SJU
$121
6/11Tue
3 stops
18h 06mMDW-SJU
$344
5/27Mon
2 stops
18h 05mMDW-SJU
$392

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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.
4/29Mon
multi-stopFrontier
9h 38mMDW-SJU
5/8Wed
multi-stopFrontier
9h 44mSJU-MDW
$197
4/30Tue
multi-stopFrontier
11h 39mMDW-SJU
5/14Tue
multi-stopFrontier
9h 49mSJU-MDW
$238
4/30Tue
multi-stopFrontier
11h 39mMDW-SJU
5/1Wed
multi-stopFrontier
9h 53mSJU-MDW
$241
4/29Mon
multi-stopFrontier
9h 38mMDW-SJU
5/2Thu
multi-stopFrontier
20h 23mSJU-MDW
$245
4/30Tue
multi-stopFrontier
12h 21mMDW-SJU
5/2Thu
multi-stopFrontier
9h 49mSJU-MDW
$246
4/29Mon
multi-stopSouthwest
8h 15mMDW-SJU
5/3Fri
multi-stopSouthwest
8h 20mSJU-MDW
$335
4/29Mon
multi-stopSouthwest
8h 15mMDW-SJU
5/3Fri
multi-stopSouthwest
11h 00mSJU-MDW
$449
4/26Fri
multi-stopDelta
10h 59mMDW-SJU
5/1Wed
multi-stopDelta
15h 09mSJU-MDW
$3,232
4/26Fri
multi-stopDelta
10h 29mMDW-SJU
4/29Mon
multi-stopDelta
8h 23mSJU-MDW
$3,396
4/26Fri
multi-stopDelta
8h 14mMDW-SJU
4/28Sun
multi-stopDelta
15h 09mSJU-MDW
$3,446

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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