SJU - MDW

$116 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 12/9. 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

KAYAK searches 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
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Everything you should know

Cheapest round-trip
$223
Overall average: $316
Frontier
Thu 10/16Tue 10/21
SJU - MDW • 1 stop
Cheapest one-way
$116
Typical prices: $78-116
Frontier
Tue 12/9
SJU - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $223 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
December
Cheapest • 30% price drop
October
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 San Juan to Midway 1 day a week: Sat.
Direct flights
Direct flights
Direct flights
Direct flights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

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

Recent round-trip flight deals from San Juan to Midway

Thu, Oct 16 - Tue, Oct 21
Frontier Logo
6:22 am - 11:25 pmSJU-MDW
18h 03m1 stop
Frontier Logo
5:56 pm - 3:24 pmMDW-SJU
20h 28m1 stop
$223Frontier
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
9:00 am - 11:25 pmSJU-MDW
15h 25m1 stop
Frontier Logo
6:26 pm - 3:33 amMDW-SJU
31h 07m1 stop
$249Frontier
Find Deal
Thu, Nov 6 - Sat, Nov 8
Frontier Logo
4:31 pm - 10:03 pmSJU-MDW
7h 32m1 stop
Frontier Logo
2:05 pm - 8:45 amMDW-SJU
16h 40m1 stop
$260Frontier
Find Deal
Fri, Jan 16 - Mon, Jan 26
Southwest Logo
11:20 am - 7:45 pmSJU-MDW
10h 25m2 stops
Southwest Logo
9:50 am - 8:55 pmMDW-SJU
9h 05m2 stops
$263Southwest
Find Deal
Thu, Oct 30 - Thu, Nov 6
Frontier Logo
7:30 am - 6:39 pmSJU-MDW
36h 09m2 stops
Frontier Logo
6:26 pm - 3:33 amMDW-SJU
31h 07m1 stop
$264Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
4:31 pm - 10:03 pmSJU-MDW
7h 32m1 stop
Frontier Logo
6:15 am - 3:19 pmMDW-SJU
7h 04m1 stop
$272Frontier
Find Deal
Fri, Jan 30 - Sun, Feb 1
Southwest Logo
6:10 am - 1:55 pmSJU-MDW
9h 45m2 stops
Southwest Logo
1:25 pm - 12:05 amMDW-SJU
8h 40m2 stops
$303Southwest
Find Deal
Wed, Oct 22 - Sun, Oct 26
Multiple Airlines Logo
4:51 pm - 8:21 pmSJU-MDW
28h 30m2 stops
Multiple Airlines Logo
9:26 pm - 2:06 pmMDW-SJU
15h 40m1 stop
$334Multiple Airlines
Find Deal
Wed, Oct 29 - Wed, Nov 5
Southwest Logo
5:05 am - 12:05 pmSJU-MDW
8h 00m2 stops
Southwest Logo
1:10 pm - 10:05 pmMDW-SJU
6h 55m1 stop
$351Southwest
Find Deal
Tue, Jan 27 - Fri, Feb 6
Southwest Logo
2:35 pm - 10:05 pmSJU-MDW
9h 30m2 stops
Southwest Logo
6:10 am - 9:50 pmMDW-SJU
13h 40m1 stop
$359Southwest
Find Deal
Booking Insights

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

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

For San Juan to Chicago Midway Airport, Friday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago Midway Airport back to San Juan, the best deals are generally found on Tuesday, with Saturday being the most expensive.

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 round-trip 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 December, where tickets cost $294 (return) on average. On the other hand, the most expensive months are July and March, where the average cost of round-trip tickets is $544 and $504 respectively.

Good to know

Low seasonFebruary
Cheapest flight$116
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 25% lower on average.
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 $116 for a one-way ticket and $223 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 Airbus A321neo 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.

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

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are Southwest and Frontier. With an average price for the route of $519 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $234 and an overall rating of 5.8.

  • 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.

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

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

Direct departures

San Juan Luis Munoz Marin Intl to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to San Juan Luis Munoz Marin Intl

Saturday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying 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
SouthwestOverall score based on 4248 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Connecting flight is on time and boarding was a breeze!

10.0 ExcellentGabriel, Sep 2025DEN - SMF
Read more Southwest reviews

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

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

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

Everything you need to know for your flight from San Juan to Midway

Information on your arrival and departure airports

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