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SJU - MDW

Find cheap flights from San Juan to Chicago Midway Airport from $109

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Juan to Midway departing on 5/14. 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
Sun 5/26
Sun 6/2

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Juan to Chicago, 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 San Juan to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,335,567 times on KAYAK, and here is why:

Save 22% 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.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Juan to Midway 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
3:08 am - 11:52 amSJU-MDW
9h 44m1 stop
10:37 am - 3:23 amMDW-SJU
15h 46m1 stop
$136Frontier
Find Deal
Wed, May 8 - Mon, May 13
3:41 pm - 11:31 pmSJU-MDW
8h 50m1 stop
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
$137Frontier
Find Deal
Sat, May 11 - Tue, May 14
3:08 am - 11:52 amSJU-MDW
9h 44m1 stop
7:49 am - 1:55 pmMDW-SJU
29h 06m1 stop
$138Frontier
Find Deal
Wed, May 8 - Thu, May 16
10:00 am - 7:27 pmSJU-MDW
10h 27m1 stop
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
$140Frontier
Find Deal
Sat, May 11 - Tue, May 14
3:08 am - 11:52 amSJU-MDW
9h 44m1 stop
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
$147Frontier
Find Deal
Wed, May 8 - Sun, May 12
2:50 am - 11:52 amSJU-MDW
10h 02m1 stop
7:17 pm - 8:34 amMDW-SJU
12h 17m1 stop
$148Frontier
Find Deal
Sat, May 11 - Mon, May 13
12:54 pm - 9:44 pmSJU-MDW
9h 50m1 stop
2:05 pm - 10:03 pmMDW-SJU
6h 58m1 stop
$428Delta
Find Deal
Tue, Oct 22 - Sat, Oct 26
12:54 pm - 9:44 pmSJU-MDW
9h 50m1 stop
6:00 am - 4:04 pmMDW-SJU
9h 04m1 stop
$599Delta
Find Deal
Thu, Oct 17 - Sun, Oct 20
5:40 am - 10:07 amSJU-MDW
29h 27m2 stops
8:00 am - 3:10 amMDW-SJU
18h 10m2 stops
Mon, Jun 17 - Thu, Jun 20
6:10 am - 5:04 pmSJU-MDW
11h 54m2 stops
6:00 am - 4:32 pmMDW-SJU
9h 32m1 stop
$3,137Delta
Find Deal
Sun, Jun 30 - Sun, Jul 7

Flights from San Juan to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from San Juan to Midway 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 San Juan to Chicago Midway Airport?

The average price of all flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Thursday and more expensive on a Saturday. On your return trip to San Juan, you should consider flying back on a Tuesday, and avoid Thursdays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport is January, where tickets cost $160 on average. On the other hand, the most expensive months are March and April, where the average cost of tickets is $331 and $322 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San Juan Luis Munoz Marin Intl Airport to Chicago Midway 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 70 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from San Juan to Chicago Midway Airport found by KAYAK users in the last 72 hours was for $136 on Frontier, followed by Delta ($428). One-way flight deals have also been found from as low as $109 on Frontier and from $202 on Delta.

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

Each day, there are between 1 and 2 nonstop flights that take off from San Juan Luis Munoz Marin Intl Airport and land in Chicago Midway Airport, with an average flight time of 5h 05m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 3 flights. The most frequent day of departure is Sunday, when 67% of all weekly flights depart. The fewest flights depart on a Saturday.

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

Early birds can take the earliest flight from San Juan Luis Munoz Marin Intl Airport at 1:20 pm and will be landing in Chicago Midway Airport at 5:25 pm.

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

If you prefer to fly at night, the latest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport jets off at 2:10 pm and lands at 6:15 pm.

Good to know

Low season

March

High season

June

Cheapest flight

$109
Best time to beat the crowds but there is an average 37% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from San Juan to Chicago Midway Airport

When to book flights from San Juan to Midway

Are your dates flexible? Find out the best times to travel from San Juan to Midway 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 San Juan to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport was $109 for a one-way ticket and $136 for a round-trip.

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

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

  • Which airports will I be using when flying from San Juan to Chicago Midway Airport?

    When flying out of San Juan you will be using San Juan Luis Munoz Marin Intl. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

    Only Delta offers inflight Wi-Fi service on the San Juan to Chicago Midway Airport flight route.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are Delta and Frontier. With an average price for the route of $551 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 $232 and an overall rating of 6.3.

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

    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 San Juan to Chicago Midway Airport.

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

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

    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 Chicago Midway Airport with an airline and back to San Juan with another airline. Booking your flights between San Juan and MDW 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 San Juan to Chicago Midway Airport?

    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 Chicago Midway Airport from San Juan 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 SJU to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $90 or less one-way.

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

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

Nonstop departures

San Juan Luis Munoz Marin Intl to Chicago Midway

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Chicago Midway to San Juan Luis Munoz Marin Intl

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from San Juan to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Juan to Chicago. 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 San Juan to Midway? 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 10966 reviews
8.2boarding
8.0entertainment
8.6crew
7.4food
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.

Flight was delayed an no one make an announcement about it., they only have Coca Cola and nothing else., the food that was served was cold… very bad experience and service

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

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

Our flight was delayed two hours. We nearly missed our connecting flight and had to rush across the airport with little kids and all their luggage. They didn’t give us enough time to walk from one gate to the other, then when we got on, we waited another half hour while the crew loaded cargo. It seems like they could have given passengers more time if they had cargo to load anyway.

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

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 San Juan to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Juan to Chicago found on KAYAK in the last 72 hours.
5/14Tue
1 stopFrontier
9h 49mSJU-MDW
$109
5/4Sat
1 stopFrontier
8h 54mSJU-MDW
$117
5/12Sun
1 stopFrontier
20h 28mSJU-MDW
$119
5/3Fri
1 stopFrontier
17h 18mSJU-MDW
$121
4/30Tue
1 stopFrontier
9h 49mSJU-MDW
$129
5/17Fri
1 stopFrontier
17h 58mSJU-MDW
$133
5/21Tue
1 stopFrontier
28h 54mSJU-MDW
$139
7/9Tue
1 stopDelta
9h 54mSJU-MDW
$202
7/4Thu
1 stopDelta
9h 54mSJU-MDW
$256
6/9Sun
2 stops
20h 47mSJU-MDW
$276

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Last minute flights from San Juan to Midway

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 San Juan to Chicago that are departing in the next 10 days.
5/1Wed
multi-stopFrontier
9h 44mSJU-MDW
5/6Mon
multi-stopFrontier
9h 38mMDW-SJU
$234
5/1Wed
multi-stopFrontier
9h 53mSJU-MDW
5/7Tue
multi-stopFrontier
11h 39mMDW-SJU
$246
5/1Wed
multi-stopFrontier
9h 44mSJU-MDW
5/6Mon
multi-stopFrontier
10h 01mMDW-SJU
$266
4/27Sat
multi-stopFrontier
10h 02mSJU-MDW
5/1Wed
multi-stopFrontier
12h 31mMDW-SJU
$298
4/27Sat
multi-stopFrontier
10h 02mSJU-MDW
4/30Tue
multi-stopFrontier
18h 04mMDW-SJU
$300
4/30Tue
multi-stopFrontier
9h 49mSJU-MDW
5/4Sat
multi-stopFrontier
13h 21mMDW-SJU
$307
4/30Tue
multi-stopFrontier
9h 49mSJU-MDW
5/4Sat
multi-stopFrontier
13h 21mMDW-SJU
$308
4/28Sun
multi-stopFrontier
12h 12mSJU-MDW
5/1Wed
multi-stopFrontier
12h 31mMDW-SJU
$328
4/29Mon
multi-stopFrontier
9h 53mSJU-MDW
5/2Thu
multi-stopFrontier
7h 19mMDW-SJU
$356
4/30Tue
multi-stopDelta
9h 40mSJU-MDW
5/4Sat
multi-stopDelta
11h 30mMDW-SJU
$3,232

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San Juan - Chicago Midway Airport Flights

Departure:

San Juan (SJU)Puerto Rico

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Juan

Cabin classes:

$141