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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
Mon 6/3
Mon 6/10

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 43,693,958 times on KAYAK, and here is why:

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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
9:24 am - 6:27 pmSJU-MDW
10h 03m1 stop
10:16 am - 11:54 pmMDW-SJU
12h 38m1 stop
$186Frontier
Find Deal
Fri, May 17 - Tue, May 21
10:18 pm - 6:54 amSJU-MDW
9h 36m1 stop
10:52 am - 11:41 pmMDW-SJU
11h 49m1 stop
$214Frontier
Find Deal
Sat, May 18 - Tue, May 28
3:41 pm - 11:31 pmSJU-MDW
8h 50m1 stop
2:44 pm - 3:23 amMDW-SJU
11h 39m1 stop
$215Frontier
Find Deal
Sat, May 11 - Tue, May 14
7:00 am - 9:48 pmSJU-MDW
15h 48m1 stop
7:23 pm - 8:30 amMDW-SJU
12h 07m1 stop
$217Frontier
Find Deal
Fri, May 17 - Sun, May 19
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
7:23 pm - 8:30 amMDW-SJU
12h 07m1 stop
$218Frontier
Find Deal
Wed, May 15 - Sun, May 19
9:34 am - 6:23 pmSJU-MDW
9h 49m1 stop
2:41 pm - 5:44 amMDW-SJU
14h 03m1 stop
$226Frontier
Find Deal
Tue, May 14 - Thu, May 16
1:30 am - 6:33 pmSJU-MDW
18h 03m1 stop
7:30 am - 8:51 pmMDW-SJU
12h 21m1 stop
Sun, May 19 - Fri, Jun 7
2:31 pm - 10:01 pmSJU-MDW
8h 30m1 stop
6:00 am - 2:44 pmMDW-SJU
7h 44m1 stop
$728Delta
Find Deal
Wed, May 8 - Wed, May 15
8:15 am - 5:59 pmSJU-MDW
10h 44m1 stop
10:11 am - 7:39 pmMDW-SJU
8h 28m1 stop
$759Delta
Find Deal
Tue, Jul 23 - Sat, Jul 27
12:52 pm - 9:48 pmSJU-MDW
9h 56m1 stop
10:41 am - 8:35 pmMDW-SJU
8h 54m1 stop
$844Delta
Find Deal
Sat, Jun 8 - Sat, Jun 15

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 $186 on Frontier, followed by Delta ($728). One-way flight deals have also been found from as low as $109 on Frontier and from $377 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 12:55 pm and will be landing in Chicago Midway Airport at 4:55 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 4:25 pm and lands at 8:20 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 $186 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 Boeing 737-800 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 $222 and an overall rating of 6.2.

  • 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 10838 reviews
7.9Comfort
7.4Food
8.6Crew
8.2Boarding
8.0Entertainment
Airline reviews

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

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

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

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

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.

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.

Delta is one of the best airlines I have flown

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...

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.

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

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
5/17Fri
1 stopFrontier
15h 48mSJU-MDW
$113
5/8Wed
1 stopFrontier
9h 44mSJU-MDW
$114
5/10Fri
1 stopFrontier
11h 58mSJU-MDW
$117
5/16Thu
1 stopFrontier
29h 30mSJU-MDW
$119
5/9Thu
1 stopFrontier
20h 23mSJU-MDW
$127
5/14Tue
1 stopFrontier
28h 46mSJU-MDW
$140
6/2Sun
3 stops
21h 36mSJU-MDW
$203
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$377
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$467

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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.
5/6Mon
multi-stopFrontier
17h 21mSJU-MDW
5/9Thu
multi-stopFrontier
11h 39mMDW-SJU
$276
5/8Wed
multi-stopFrontier
9h 53mSJU-MDW
5/15Wed
multi-stopFrontier
12h 31mMDW-SJU
$278
5/7Tue
multi-stopFrontier
9h 49mSJU-MDW
5/8Wed
multi-stopFrontier
12h 17mMDW-SJU
$338
5/5Sun
multi-stopFrontier
20h 28mSJU-MDW
5/9Thu
multi-stopFrontier
11h 39mMDW-SJU
$410
5/8Wed
multi-stopDelta
8h 30mSJU-MDW
5/15Wed
multi-stopDelta
7h 44mMDW-SJU
$728
5/8Wed
multi-stopDelta
7h 06mSJU-MDW
5/15Wed
multi-stopDelta
13h 20mMDW-SJU
$3,300
5/8Wed
multi-stopDelta
7h 06mSJU-MDW
5/15Wed
multi-stopDelta
11h 24mMDW-SJU
$3,893

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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