SJU - MDW

$107 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 12/20. 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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Everything you should know

Cheapest round-trip
$195
Typical prices: $260-$440
Frontier
Fri 12/19Sun 1/4
SJU - MDW • 1 stop
Cheapest one-way
$107
Typical prices: $78-$145
Frontier
Sat 12/20
SJU - MDW • 2 stops
Top airlines
Frontier
Cheapest • from $195 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
December
Cheapest • 29% price drop
April
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

Fri, Dec 19 - Sun, Jan 4
Frontier Logo
3:55 am - 9:04 pmSJU-MDW
19h 09m1 stop
Frontier Logo
6:00 am - 1:37 amMDW-SJU
17h 37m1 stop
$195Frontier
Find Deal
Mon, Nov 24 - Wed, Nov 26
Frontier Logo
7:09 pm - 5:15 pmSJU-MDW
24h 06m1 stop
Frontier Logo
5:30 pm - 9:12 pmMDW-SJU
25h 42m1 stop
$206Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Frontier Logo
4:31 pm - 10:12 pmSJU-MDW
7h 41m1 stop
Frontier Logo
3:10 pm - 2:50 amMDW-SJU
9h 40m1 stop
$211Frontier
Find Deal
Thu, Dec 18 - Fri, Jan 9
Frontier Logo
4:21 pm - 10:12 pmSJU-MDW
7h 51m1 stop
Frontier Logo
6:00 am - 12:59 pmMDW-SJU
28h 59m1 stop
$212Frontier
Find Deal
Fri, Dec 26 - Sat, Jan 3
Frontier Logo
3:54 am - 10:12 pmSJU-MDW
44h 18m2 stops
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$217Frontier
Find Deal
Wed, Dec 24 - Sat, Jan 3
Frontier Logo
4:16 pm - 5:38 pmSJU-MDW
27h 22m1 stop
Frontier Logo
2:24 pm - 2:39 amMDW-SJU
10h 15m1 stop
$219Frontier
Find Deal
Thu, Dec 11 - Sat, Dec 13
Multiple Airlines Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Multiple Airlines Logo
2:59 pm - 7:50 pmMDW-SJU
26h 51m1 stop
$221Multiple Airlines
Find Deal
Fri, Dec 19 - Sun, Jan 4
Multiple Airlines Logo
3:54 am - 1:21 pmSJU-MDW
11h 27m2 stops
Multiple Airlines Logo
6:00 am - 1:37 amMDW-SJU
17h 37m1 stop
$223Multiple Airlines
Find Deal
Sat, Dec 27 - Thu, Jan 1
Frontier Logo
7:35 am - 10:12 pmSJU-MDW
16h 37m2 stops
Frontier Logo
6:12 am - 12:37 amMDW-SJU
16h 25m1 stop
$225Frontier
Find Deal
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
4:11 pm - 11:25 pmSJU-MDW
9h 14m1 stop
Frontier Logo
8:00 am - 12:45 amMDW-SJU
15h 45m1 stop
$226Frontier
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.

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 December.

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 April, where the average cost of round-trip tickets is $544 and $489 respectively.

Good to know

Low seasonFebruary
Cheapest flight$107
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 18% 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 $107 for a one-way ticket and $195 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 $566 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 $265 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 4236 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

2.0 MediocreCharity, Nov 2025MSP - MDW
Read more Southwest reviews

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

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

Information on your arrival and departure airports