SJU - MDW

$137 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 6/3. 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

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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from San Juan to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Juan to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
6:00 am - 5:30 pmSJU-MDW
12h 30m1 stop
Frontier Logo
1:19 pm - 10:01 pmMDW-SJU
7h 42m1 stop
$298Frontier
Find Deal
Sun, May 11 - Fri, May 16
Frontier Logo
3:56 am - 12:24 pmSJU-MDW
9h 28m1 stop
Frontier Logo
12:15 pm - 1:50 amMDW-SJU
12h 35m1 stop
$299Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
3:56 am - 5:30 pmSJU-MDW
14h 34m1 stop
Frontier Logo
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
$303Frontier
Find Deal
Sat, May 10 - Mon, May 12
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
Frontier Logo
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
$304Frontier
Find Deal
Fri, May 16 - Mon, May 19
Delta Logo
2:39 pm - 9:47 pmSJU-MDW
8h 08m1 stop
Delta Logo
6:00 am - 4:50 pmMDW-SJU
9h 50m1 stop
$391Delta
Find Deal
Thu, Aug 28 - Tue, Sep 2
Southwest Logo
1:20 pm - 10:30 pmSJU-MDW
10h 10m1 stop
Southwest Logo
7:30 am - 2:55 pmMDW-SJU
6h 25m1 stop
$397Southwest
Find Deal
Thu, Sep 11 - Tue, Sep 16
Southwest Logo
5:50 am - 2:00 pmSJU-MDW
9h 10m2 stops
Southwest Logo
6:05 am - 3:10 pmMDW-SJU
8h 05m1 stop
$418Southwest
Find Deal
Thu, Aug 28 - Mon, Sep 1
Delta Logo
1:06 pm - 9:41 pmSJU-MDW
9h 35m1 stop
Delta Logo
6:00 am - 4:50 pmMDW-SJU
9h 50m1 stop
$429Delta
Find Deal
Fri, Aug 8 - Mon, Aug 11
 Logo
1:59 am - 2:04 pmSJU-MDW
13h 05m2 stops
 Logo
9:12 am - 12:54 amMDW-SJU
38h 42m3 stops
Thu, May 22 - Mon, May 26
 Logo
4:46 pm - 2:04 pmSJU-MDW
22h 18m2 stops
 Logo
4:27 pm - 9:56 amMDW-SJU
40h 29m3 stops
Thu, Jul 17 - Wed, Aug 6
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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 $252 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $510 and $504 respectively.

Can I save money by flying with a layover from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $310 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from San Juan Luis Munoz Marin Intl Airport to Chicago Midway Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonFebruary
High seasonNovember
Cheapest flight$137
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 20% increase in price.
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 $137 for a one-way ticket and $298 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 737-800 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 $435 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 $278 and an overall rating of 5.9.

  • 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $244 or less one-way.

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

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
See more direct flights

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 4294 reviews
7.6Entertainment
7.1Food
8.6Crew
8.0Comfort
8.2Boarding
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

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

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