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SJU - MDW

Find cheap flights from San Juan to Chicago Midway Airport from $73

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 5/22. 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
Thu 6/6
Thu 6/13

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 43,707,506 times on KAYAK, and here is why:

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

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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
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
$175Frontier
Find Deal
Fri, May 17 - Mon, May 20
9:24 am - 6:27 pmSJU-MDW
10h 03m1 stop
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
$178Frontier
Find Deal
Fri, May 17 - Mon, May 20
10:18 pm - 6:54 amSJU-MDW
9h 36m1 stop
10:52 am - 11:41 pmMDW-SJU
11h 49m1 stop
$180Frontier
Find Deal
Sat, May 18 - Tue, May 21
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
6:48 am - 9:53 pmSJU-MDW
16h 05m1 stop
10:16 am - 11:54 pmMDW-SJU
12h 38m1 stop
$211Frontier
Find Deal
Wed, May 22 - Tue, May 28
10:47 pm - 11:33 amSJU-MDW
13h 46m1 stop
8:13 pm - 8:47 amMDW-SJU
11h 34m1 stop
$214Frontier
Find Deal
Tue, Aug 20 - Wed, Sep 4
8:15 am - 5:14 pmSJU-MDW
9h 59m1 stop
10:11 am - 10:09 pmMDW-SJU
10h 58m1 stop
$473Delta
Find Deal
Sat, Aug 17 - Tue, Aug 20
12:54 pm - 9:44 pmSJU-MDW
9h 50m1 stop
6:00 am - 4:04 pmMDW-SJU
9h 04m1 stop
$604Delta
Find Deal
Thu, Oct 17 - Sun, Oct 20
2:25 pm - 9:44 pmSJU-MDW
8h 19m1 stop
10:11 am - 10:03 pmMDW-SJU
10h 52m1 stop
$619Delta
Find Deal
Tue, Oct 22 - Sat, Oct 26
12:59 am - 4:17 pmSJU-MDW
16h 18m3 stops
11:05 am - 3:30 amMDW-SJU
15h 25m2 stops
Tue, May 21 - Wed, May 29

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 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 1 week 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 $175 on Frontier, followed by Delta ($473). One-way flight deals have also been found from as low as $73 on Frontier and from $452 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

December

Cheapest flight

$73
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 $73 for a one-way ticket and $175 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 $217 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 10810 reviews
8.2Boarding
7.9Comfort
7.4Food
8.0Entertainment
8.6Crew
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

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.

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.

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.

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

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.

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.
5/22Wed
1 stopFrontier
16h 05mSJU-MDW
$73
5/15Wed
1 stopFrontier
9h 53mSJU-MDW
$109
5/14Tue
1 stopFrontier
28h 46mSJU-MDW
$119
5/16Thu
1 stopFrontier
29h 30mSJU-MDW
$120
5/14Tue
1 stopFrontier
27h 46mSJU-MDW
$128
5/14Tue
1 stopFrontier
9h 49mSJU-MDW
$129
5/29Wed
3 stops
31h 51mSJU-MDW
$295
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$452
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$467
5/20Mon
1 stopDelta
8h 25mSJU-MDW
$1,027

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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.
5/9Thu
multi-stopFrontier
9h 49mSJU-MDW
5/14Tue
multi-stopFrontier
10h 16mMDW-SJU
$277
5/8Wed
multi-stopFrontier
9h 44mSJU-MDW
5/13Mon
multi-stopFrontier
9h 12mMDW-SJU
$278
5/11Sat
multi-stopFrontier
8h 50mSJU-MDW
5/18Sat
multi-stopFrontier
8h 35mMDW-SJU
$279
5/12Sun
multi-stopFrontier
20h 28mSJU-MDW
5/15Wed
multi-stopFrontier
12h 27mMDW-SJU
$284
5/8Wed
multi-stopFrontier
9h 53mSJU-MDW
5/15Wed
multi-stopFrontier
12h 31mMDW-SJU
$298
5/8Wed
multi-stopFrontier
9h 53mSJU-MDW
5/15Wed
multi-stopFrontier
9h 38mMDW-SJU
$299
5/9Thu
multi-stopFrontier
20h 23mSJU-MDW
5/13Mon
multi-stopFrontier
21h 28mMDW-SJU
$303
5/8Wed
multi-stopFrontier
9h 44mSJU-MDW
5/14Tue
multi-stopFrontier
10h 16mMDW-SJU
$306
5/11Sat
multi-stopDelta
7h 06mSJU-MDW
5/14Tue
multi-stopDelta
13h 20mMDW-SJU
$3,248
5/8Wed
multi-stopDelta
10h 12mSJU-MDW
5/15Wed
multi-stopDelta
13h 20mMDW-SJU
$3,795

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San Juan - Chicago Midway Airport Flights

Departure:

San Juan (undefined)Puerto Rico

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Juan

Cabin classes:

$141