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MDW - SJU

Find cheap flights from Chicago Midway Airport to San Juan from $74

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 5/21. 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
Fri 6/7
Fri 6/14

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 43,968,530 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 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
5:45 pm - 9:30 amMDW-SJU
14h 45m1 stop
6:48 am - 9:53 pmSJU-MDW
16h 05m1 stop
$188Frontier
Find Deal
Sat, May 18 - Wed, May 22
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
9:45 am - 12:20 amSJU-MDW
15h 35m1 stop
$212Frontier
Find Deal
Wed, May 22 - Thu, Jun 6
10:52 am - 11:41 pmMDW-SJU
11h 49m1 stop
8:18 pm - 6:54 amSJU-MDW
11h 36m1 stop
$213Frontier
Find Deal
Tue, May 21 - Sat, Jun 1
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
7:10 am - 8:30 pmSJU-MDW
14h 20m1 stop
$214Frontier
Find Deal
Wed, May 22 - Thu, May 30
10:52 am - 11:41 pmMDW-SJU
11h 49m1 stop
7:00 am - 9:48 pmSJU-MDW
15h 48m1 stop
$217Frontier
Find Deal
Tue, May 21 - Fri, May 31
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
9:29 am - 6:27 pmSJU-MDW
9h 58m1 stop
$218Frontier
Find Deal
Wed, May 22 - Fri, May 31
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
10:35 am - 12:31 amSJU-MDW
14h 56m1 stop
$219Frontier
Find Deal
Wed, May 22 - Tue, May 28
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
3:04 am - 12:20 pmSJU-MDW
10h 16m1 stop
$221Frontier
Find Deal
Wed, May 22 - Thu, May 30
10:16 am - 11:54 pmMDW-SJU
12h 38m1 stop
7:10 am - 8:30 pmSJU-MDW
14h 20m1 stop
$228Frontier
Find Deal
Tue, May 21 - Thu, May 23
10:00 am - 9:47 pmMDW-SJU
10h 47m1 stop
10:47 pm - 10:55 amSJU-MDW
13h 08m1 stop
$235Frontier
Find Deal
Thu, Sep 26 - Wed, Oct 2

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 Wednesday 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 Mondays.

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 October, 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 $511 and $410 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 56 days before departure.

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

Each day, there are between 1 and 2 nonstop flights that take off from Chicago Midway Airport and land in San Juan Luis Munoz Marin Intl Airport, with an average flight time of 4h 41m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 3 flights. The most frequent day of departure is Saturday, when 67% of all weekly flights depart. The fewest flights depart on a Sunday.

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 8:05 am and will be landing in San Juan Luis Munoz Marin Intl Airport at 1:55 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

December

Cheapest flight

$74
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 26% increase in price.
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 $74 for a one-way ticket and $188 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 10789 reviews
8.6Crew
7.4Food
8.0Entertainment
8.2Boarding
7.9Comfort
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

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!

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.

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

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.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

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 checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

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.

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.
5/21Tue
1 stopFrontier
12h 38mMDW-SJU
$74
5/18Sat
1 stopFrontier
10h 15mMDW-SJU
$84
5/17Fri
1 stopFrontier
11h 45mMDW-SJU
$109
5/13Mon
1 stopFrontier
12h 17mMDW-SJU
$113
8/20Tue
1 stopFrontier
12h 11mMDW-SJU
$117
5/23Thu
1 stopFrontier
8h 05mMDW-SJU
$122
9/6Fri
1 stopFrontier
10h 47mMDW-SJU
$124
5/25Sat
1 stopFrontier
8h 24mMDW-SJU
$126
6/7Fri
2 stops
10h 07mMDW-SJU
$213
6/7Fri
2 stops
10h 07mMDW-SJU
$214

Search by stops

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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.
5/13Mon
multi-stopFrontier
9h 12mMDW-SJU
5/22Wed
multi-stopFrontier
16h 05mSJU-MDW
$248
5/10Fri
multi-stopFrontier
9h 35mMDW-SJU
5/15Wed
multi-stopFrontier
11h 43mSJU-MDW
$278
5/10Fri
multi-stopFrontier
18h 04mMDW-SJU
5/14Tue
multi-stopFrontier
28h 46mSJU-MDW
$284
5/13Mon
multi-stopFrontier
12h 17mMDW-SJU
5/14Tue
multi-stopFrontier
28h 46mSJU-MDW
$287
5/10Fri
multi-stopFrontier
9h 35mMDW-SJU
5/16Thu
multi-stopFrontier
29h 30mSJU-MDW
$295
5/11Sat
multi-stopFrontier
13h 21mMDW-SJU
5/14Tue
multi-stopFrontier
28h 46mSJU-MDW
$296
5/12Sun
multi-stopFrontier
7h 36mMDW-SJU
5/19Sun
multi-stopFrontier
14h 20mSJU-MDW
$308
5/10Fri
multi-stopFrontier
9h 35mMDW-SJU
5/29Wed
multi-stopFrontier
11h 45mSJU-MDW
$314
5/10Fri
multi-stopDelta
8h 14mMDW-SJU
5/29Wed
multi-stopDelta
15h 01mSJU-MDW
$3,338
5/10Fri
multi-stopDelta
11h 24mMDW-SJU
5/16Thu
multi-stopDelta
10h 12mSJU-MDW
$3,957

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Chicago Midway Airport - San Juan Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

San Juan (SJU)Puerto Rico

Return flight deals:

San Juan - Chicago Midway Airport

Cabin classes:

$59