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SJU - MDW

$69 Find cheap flights from San Juan to Chicago Midway Airport

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 6/25. 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
Wed 7/10
Wed 7/17

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 42,898,604 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
3:08 am - 9:31 amSJU-MDW
7h 23m1 stop
12:06 pm - 2:03 amMDW-SJU
12h 57m1 stop
$137Frontier
Find Deal
Sat, Jun 22 - Mon, Jun 24
9:05 am - 7:31 amSJU-MDW
23h 26m1 stop
5:14 pm - 1:59 amMDW-SJU
7h 45m1 stop
$143Frontier
Find Deal
Sun, Jun 23 - Mon, Jun 24
4:38 pm - 7:53 pmSJU-MDW
28h 15m1 stop
3:29 pm - 1:48 amMDW-SJU
9h 19m1 stop
$161Frontier
Find Deal
Fri, Jun 21 - Wed, Jun 26
8:41 pm - 8:36 amSJU-MDW
12h 55m1 stop
6:20 am - 2:30 amMDW-SJU
19h 10m1 stop
$168Frontier
Find Deal
Tue, Jul 9 - Wed, Jul 24
8:41 pm - 8:36 amSJU-MDW
12h 55m1 stop
7:37 pm - 3:12 amMDW-SJU
6h 35m1 stop
$183Frontier
Find Deal
Thu, Aug 1 - Tue, Aug 6
10:36 am - 12:17 amSJU-MDW
14h 41m1 stop
6:20 am - 2:30 amMDW-SJU
19h 10m1 stop
$184Frontier
Find Deal
Thu, Jul 18 - Wed, Jul 24
8:15 am - 5:59 pmSJU-MDW
10h 44m1 stop
6:00 am - 4:04 pmMDW-SJU
9h 04m1 stop
$370Delta
Find Deal
Fri, Oct 25 - Mon, Oct 28
2:11 pm - 9:44 pmSJU-MDW
9h 33m1 stop
1:05 pm - 11:03 pmMDW-SJU
7h 58m1 stop
$377Delta
Find Deal
Fri, Dec 6 - Mon, Dec 9
2:25 pm - 9:44 pmSJU-MDW
8h 19m1 stop
6:00 am - 4:04 pmMDW-SJU
9h 04m1 stop
$424Delta
Find Deal
Thu, Oct 24 - Sun, Oct 27
7:54 pm - 12:06 pmSJU-MDW
17h 12m2 stops
11:05 am - 2:05 amMDW-SJU
14h 00m2 stops
Thu, Aug 22 - Wed, Aug 28

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 Friday and more expensive on a Monday. On your return trip to San Juan, you should consider flying back on a Wednesday, 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 September, where tickets cost $165 on average. On the other hand, the most expensive months are April and March, where the average cost of tickets is $329 and $288 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 2 days 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 $137 on Frontier, followed by Delta ($370). One-way flight deals have also been found from as low as $69 on Frontier and from $172 on Delta.

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

There is a maximum of 1 nonstop flight a day that takes off from San Juan Luis Munoz Marin Intl Airport and lands in Chicago Midway Airport, with an average flight time of 5h 00m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 2 flights.

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

December

Cheapest flight

$69
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 4% 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 $69 for a one-way ticket and $137 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 $214 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

KAYAK’s top tips for finding a cheap flight from San Juan Luis Munoz Marin Intl Airport 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 10295 reviews
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Ongoing flight was delayed. Staff at bag recheck was able to get us on an earlier flight. With only 20 minutes till take off we feared our bags would not make the new earlier flight. We were most delighted that they did and were there when we landed. Delta came through

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

The flight was fine. The itinerary change from original booking was not good. We were originally leaving at 12:50 pm. The change to 8:29pm put us getting home in the early morning hours the next day. Then having to wait over an hour on the ground for a parking place to get off the plane was exhausting.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

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.

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

When we arrived we lasted 48 minutes to be able to get off the plane without air and the plane turned off more than half of the passengers because after they started to leave they realized that the bridge was defective

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

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.
6/25Tue
1 stopFrontier
10h 02mSJU-MDW
$69
6/25Tue
1 stopFrontier
11h 50mSJU-MDW
$75
7/9Tue
1 stopFrontier
12h 55mSJU-MDW
$84
7/2Tue
1 stopFrontier
10h 02mSJU-MDW
$89
7/10Wed
1 stopFrontier
26h 05mSJU-MDW
$95
8/8Thu
2 stopsFrontier
17h 42mSJU-MDW
$98
6/18Tue
2 stops
16h 40mSJU-MDW
$114
12/3Tue
1 stopDelta
11h 44mSJU-MDW
$172
8/17Sat
1 stopDelta
8h 27mSJU-MDW
$252
12/2Mon
1 stopDelta
11h 44mSJU-MDW
$372

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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.
6/13Thu
multi-stopFrontier
11h 50mSJU-MDW
6/20Thu
multi-stopFrontier
11h 32mMDW-SJU
$175
6/13Thu
multi-stopFrontier
11h 50mSJU-MDW
6/20Thu
multi-stopFrontier
11h 32mMDW-SJU
$178
6/14Fri
multi-stopFrontier
12h 58mSJU-MDW
6/17Mon
multi-stopFrontier
28h 52mMDW-SJU
$205
6/13Thu
multi-stopFrontier
29h 56mSJU-MDW
6/17Mon
multi-stopFrontier
28h 52mMDW-SJU
$211
6/11Tue
multi-stopFrontier
22h 52mSJU-MDW
6/14Fri
multi-stopFrontier
25h 52mMDW-SJU
$229
6/12Wed
multi-stopFrontier
15h 09mSJU-MDW
6/30Sun
multi-stopFrontier
11h 42mMDW-SJU
$255
6/12Wed
multi-stopFrontier
15h 09mSJU-MDW
6/15Sat
multi-stopFrontier
23h 51mMDW-SJU
$257
6/11Tue
multi-stopFrontier
22h 52mSJU-MDW
6/17Mon
multi-stopFrontier
8h 30mMDW-SJU
$263
6/12Wed
multi-stopFrontier
7h 23mSJU-MDW
6/20Thu
multi-stopFrontier
11h 32mMDW-SJU
$285
6/12Wed
multi-stopFrontier
7h 23mSJU-MDW
6/20Thu
multi-stopFrontier
11h 32mMDW-SJU
$288

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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