SJU - MDW

$123 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 9/7. 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 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$241
Typical prices: $284-$394
Southwest
Thu 8/20Thu 8/20
SJU - MDW • 1 stop
Cheapest one-way
$123
Typical prices: $113-$488
Southwest
Mon 9/7
SJU - MDW • 1 stop
Nonstop flights
2 days a week
Sat, Sun
You can fly direct with Southwest. Average duration is 4h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Southwest
Cheapest • from $241 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Atlanta (ATL)
Cheapest • Avg $284 (round-trip)
Orlando (MCO)
Shortest trip • 7h 08m (one-way)
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 100% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Aug 20 - Thu, Aug 20
Southwest Logo
6:00 am - 12:40 pm
SJU
-
MDW
7h 40m
1 stop
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$241Southwest
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
$246Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
1:20 pm - 7:10 pm
SJU
-
MDW
6h 50m
1 stop
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
$256Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
Southwest Logo
7:50 am - 6:05 pm
MDW
-
SJU
9h 15m
2 stops
$266Southwest
Fri, Aug 28 - Mon, Aug 31
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$281Delta
Thu, Jul 23 - Thu, Aug 27
Southwest Logo
10:20 pm - 10:00 am
SJU
-
MDW
12h 40m
1 stop
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
$286Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$296Southwest
Wed, Sep 2 - Mon, Sep 7
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
1 stop
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$301Southwest
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
2:35 pm - 9:30 pm
SJU
-
MDW
7h 55m
1 stop
Southwest Logo
5:00 am - 1:45 pm
MDW
-
SJU
7h 45m
1 stop
$306Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
5:05 am - 12:35 pm
SJU
-
MDW
8h 30m
1 stop
Southwest Logo
1:55 pm - 11:10 pm
MDW
-
SJU
8h 15m
2 stops
$311Southwest
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.

How much is a round-trip flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway 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 San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport departing in August.

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 March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are February and January, where the average cost of round-trip tickets is $726 and $540 respectively.

Find deals

Good to know

Low seasonAugust
Cheapest flight$123
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 19% 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

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

    There is a maximum of 1 nonstop flight a day that takes off from San Juan Luis Munoz Marin Intl Airport and lands in Chicago Midway Airport, with an average flight time of 4h 50m. The most common departure time is 4:00 pm and most flights take off at night. Each week, there are 2 flights.

  • What is the cheapest flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport was $123 for a one-way ticket and $241 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 MAX 8 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.

  • 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

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to San Juan Luis Munoz Marin Intl

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline 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.
7.9
SouthwestOverall score based on 4247 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

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

Information on your arrival and departure airports

San Juan (SJU)
Midway (MDW)