MDW - SJU

$113 Find Cheap Flights from Chicago Midway Airport to San Juan

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 11/27. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to San Juan Luis Munoz Marin Intl Airport

 
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
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Everything you should know

Cheapest round-trip
$215
Typical prices: $271-$469
Frontier
Sun 1/11Thu 1/15
MDW - SJU • 1 stop
Cheapest non-stop
$485
Southwest
Sat 1/10Sat 1/17
MDW - SJU • Non-stop
Top airlines
Frontier
Cheapest • from $215 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
May
Cheapest • 22% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
1 day a week
There are direct flights from Midway to San Juan 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
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We hope you love your trip to San Juan!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Juan

Sun, Jan 11 - Thu, Jan 15
Frontier Logo
10:18 am - 2:50 amMDW-SJU
14h 32m1 stop
Frontier Logo
8:00 am - 2:47 pmSJU-MDW
8h 47m1 stop
$215Frontier
Find Deal
Thu, Nov 13 - Tue, Nov 25
Frontier Logo
10:12 am - 2:54 amMDW-SJU
14h 42m1 stop
Frontier Logo
9:30 pm - 4:57 pmSJU-MDW
21h 27m1 stop
$221Frontier
Find Deal
Thu, Nov 27 - Thu, Dec 4
Frontier Logo
6:15 pm - 9:27 amMDW-SJU
37h 12m2 stops
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
$222Frontier
Find Deal
Wed, Jan 7 - Sun, Jan 11
Frontier Logo
3:52 pm - 1:42 amMDW-SJU
7h 50m1 stop
Frontier Logo
3:55 am - 9:13 amSJU-MDW
7h 18m1 stop
$223Frontier
Find Deal
Sun, Feb 22 - Sat, Feb 28
Frontier Logo
6:30 am - 1:42 amMDW-SJU
17h 12m1 stop
Frontier Logo
4:11 pm - 11:25 pmSJU-MDW
9h 14m1 stop
$225Frontier
Find Deal
Mon, Jan 19 - Fri, Jan 23
Delta Logo
6:00 am - 2:30 pmMDW-SJU
6h 30m1 stop
Delta Logo
6:15 am - 12:01 pmSJU-MDW
7h 46m1 stop
$227Delta
Find Deal
Sat, Jan 31 - Wed, Feb 4
Southwest Logo
8:20 am - 2:55 pmMDW-SJU
4h 35mnonstop
Southwest Logo
5:40 am - 12:30 pmSJU-MDW
8h 50m2 stops
$248Southwest
Find Deal
Mon, Jan 19 - Fri, Jan 23
Southwest Logo
1:25 pm - 12:05 amMDW-SJU
8h 40m2 stops
Southwest Logo
6:10 am - 11:35 amSJU-MDW
7h 25m1 stop
$252Southwest
Find Deal
Sun, Jan 18 - Thu, Jan 22
Southwest Logo
1:50 pm - 12:35 amMDW-SJU
8h 45m2 stops
Southwest Logo
6:10 am - 1:55 pmSJU-MDW
9h 45m2 stops
$267Southwest
Find Deal
Wed, Jan 21 - Sat, Jan 31
Southwest Logo
6:50 am - 7:05 pmMDW-SJU
10h 15m2 stops
Southwest Logo
5:30 am - 2:45 pmSJU-MDW
11h 15m2 stops
$277Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to San Juan flights

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.

How much is a round-trip flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport departing in January.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Juan?

The average price of all round-trip flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to San Juan on a Tuesday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, and avoid Saturdays for better deals.

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 round-trip 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 May, where tickets cost $328 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $554 and $499 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$113
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 23% 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 $113 for a one-way ticket and $215 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 Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Juan flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to San Juan?

    Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago Midway Airport and San Juan, with Star Alliance being the most commonly used for this 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.

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Southwest and Delta. With an average price for the route of $503 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $405 and an overall rating of 7.9.

  • 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $686 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to San Juan?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Juan Luis Munoz Marin Intl.
Find which airlines fly direct from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Juan Luis Munoz Marin Intl

Saturday

Southwest

Southwest

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

Reviews of the top 5 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
SouthwestOverall score based on 4242 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

No Tumberlence smooth flight. Try to change the menu on Snacks.

It was a good an early bird pleasant and quiet

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The spirit flight was on time. The airplane itself was surprisingly very nice. We had great seats. Seems like there's more room. Only complaint is that I didn't get a full refund for my mistakenly buying the baggage twice.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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