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MDW - SJU

Find cheap flights from Chicago Midway Airport to San Juan from $90

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 5/8. 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 4/28
Sun 5/5

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 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Midway to San Juan

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
7:10 am - 1:31 amMDW-SJU
17h 21m1 stop
3:41 pm - 6:27 pmSJU-MDW
27h 46m1 stop
Tue, Apr 9 - Tue, Apr 16
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
$158Frontier
Find Deal
Tue, Apr 23 - Wed, May 1
3:11 pm - 1:57 amMDW-SJU
9h 46m1 stop
9:34 am - 6:23 pmSJU-MDW
9h 49m1 stop
$159Frontier
Find Deal
Tue, Apr 9 - Tue, Apr 23
3:11 pm - 1:57 amMDW-SJU
9h 46m1 stop
9:34 am - 6:23 pmSJU-MDW
9h 49m1 stop
$164Frontier
Find Deal
Tue, Apr 9 - Tue, Apr 16
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
$166Frontier
Find Deal
Tue, Apr 16 - Fri, Apr 26
7:17 pm - 8:34 amMDW-SJU
12h 17m1 stop
9:34 am - 6:23 pmSJU-MDW
9h 49m1 stop
$172Frontier
Find Deal
Mon, May 6 - Tue, May 14
3:11 pm - 1:57 amMDW-SJU
9h 46m1 stop
9:34 am - 7:49 pmSJU-MDW
11h 15m2 stops
$174Frontier
Find Deal
Tue, Apr 9 - Tue, Apr 23
7:17 pm - 6:57 pmMDW-SJU
22h 40m1 stop
6:43 pm - 6:27 pmSJU-MDW
24h 44m1 stop
Wed, May 15 - Tue, May 21
12:53 pm - 1:56 amMDW-SJU
12h 03m2 stops
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
$176Frontier
Find Deal
Tue, Apr 23 - Wed, May 1
4:20 pm - 8:34 amMDW-SJU
15h 14m2 stops
9:34 am - 6:23 pmSJU-MDW
9h 49m1 stop
$179Frontier
Find Deal
Tue, Apr 9 - Tue, Apr 16

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 Saturdays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

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 September, 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 $556 and $523 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 70 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 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 35m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 4 flights and there are the same amount of flights each day 2.

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.

How long does a flight from Chicago Midway Airport to San Juan take?

Nonstop flights from Chicago Midway Airport generally make it to San Juan in 6h 56m. The flying distance between the two cities is 2,057 miles.

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 8:30 am and will be landing in San Juan Luis Munoz Marin Intl Airport at 2:00 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 2:20 pm.

Good to know

Low season

April

High season

May

Cheapest flight

$90
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 9% lower on average.
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 $90 for a one-way ticket and $157 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.

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Delta and Frontier. With an average price for the route of $718 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 $252 and an overall rating of 6.3.

  • 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

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
80entertainment
81overall
82boarding
79comfort
75food
86crew
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Had to run to make it only to have the flight delayed to wait for all the late connectors Second drink service skipped up

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

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.

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

See my previous comment which is mostly about our flight from Phoenix to SFO

Terrible. Initially we were shocked by the outrageous baggage fees we needed to pay at check in for our so-called "discounted, economy flight" - we paid over $200 (!!) for one check-in and 2 carry-on bags - this felt like a real bait-and-switch" scam. Our flight from Phoenix to SFO was delayed by 4 hours. Multiple apparent causes (from needing to make space for other planes that were landing late to problem with cabins pressure system, and whatever...). After de-boarding and re-boarding we still waited at least an hour on a cramped, poorly ventilated plane before take-off. Seats were cramped, uncomfortable - did not recline at all. No water until we were flying for a while. No complimentary snacks. Upon arrival at SFO my luggage was sent upstairs to the check-in counter. The customer service person there refused to let me examine a bunch of bags that were sitting on a nearby cart because it was "behind the counter", rather made me wait until another attendant did an exhaustive and failed (?computer) search, came back and told me they were unable to locate my bag. I asked her to look on the cart, lo and behold, there was my bag just a few feet away! Missed my choir rehearsal that evening due to all of the delays. One more thing, a few days later my husband and I tested positive for Covid. Since we both are fully vaccinated, careful about masking and have never had Covid previously, we will never know, but suspect we may have acquired the infection during the prolonged wait on your poorly ventilated plane (person in the row in front of us was coughing). After registering a complaint, we received a measly $50 voucher for future flights. Needless to say we have no intention of flying with Frontier Airlines ever again.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

The whole experience was bad. Didn't know no complimentary drinks or snacks. $4.39 for a soda is ridiculous even a bottle water. A carry on was $74 just crazy. I don't think I will take this airline ever again. Very bad

Delayed...attendants checked every single bag and item for sizes before boarding.

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.
5/8Wed
1 stopFrontier
12h 17mMDW-SJU
$90
5/1Wed
1 stop
13h 07mMDW-SJU
$98
4/2Tue
1 stopFrontier
29h 18mMDW-SJU
$99
5/1Wed
2 stops
11h 02mMDW-SJU
$103
5/1Wed
2 stops
11h 02mMDW-SJU
$107
4/10Wed
1 stopFrontier
12h 17mMDW-SJU
$108
5/1Wed
1 stop
22h 45mMDW-SJU
$109
8/20Tue
1 stopDelta
6h 29mMDW-SJU
$172
4/3Wed
1 stopDelta
10h 38mMDW-SJU
$412
4/3Wed
1 stopDelta
11h 07mMDW-SJU
$637

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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.
4/2Tue
multi-stopFrontier
29h 18mMDW-SJU
4/8Mon
multi-stopFrontier
12h 14mSJU-MDW
$235
4/2Tue
multi-stop
29h 18mMDW-SJU
4/8Mon
multi-stop
23h 58mSJU-MDW
$238
4/2Tue
multi-stopFrontier
16h 16mMDW-SJU
4/7Sun
multi-stopFrontier
17h 43mSJU-MDW
$252
4/2Tue
multi-stopFrontier
16h 16mMDW-SJU
4/4Thu
multi-stopFrontier
29h 31mSJU-MDW
$254
4/2Tue
multi-stopFrontier
16h 16mMDW-SJU
4/3Wed
multi-stopFrontier
18h 22mSJU-MDW
$255
4/2Tue
multi-stopFrontier
26h 07mMDW-SJU
4/3Wed
multi-stopFrontier
29h 43mSJU-MDW
$265
4/1Mon
multi-stop
25h 50mMDW-SJU
4/8Mon
multi-stop
12h 14mSJU-MDW
$306
4/1Mon
multi-stopDelta
8h 45mMDW-SJU
4/10Wed
multi-stopDelta
14h 59mSJU-MDW
$3,225
4/1Mon
multi-stopDelta
9h 00mMDW-SJU
4/6Sat
multi-stopDelta
8h 21mSJU-MDW
$3,734
3/31Sun
multi-stopDelta
12h 27mMDW-SJU
4/7Sun
multi-stopDelta
10h 15mSJU-MDW
$4,143

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Chicago Midway Airport - San Juan Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

San Juan (SJU)Puerto Rico

Return flight deals:

San Juan - Chicago Midway Airport

Cabin classes:

$59