SJU - MDW

$95 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 3/5. 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
$198
Overall average: $448
Multiple Airlines
Wed 2/25Sun 3/1
SJU - MDW • 2 stops
Cheapest non-stop
$527
Southwest
Sat 6/27Sat 7/4
SJU - MDW • Non-stop
Top airlines
Frontier
Cheapest • from $202 (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
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
2 days a week
There are direct flights from San Juan to Midway 2 days a week: Sat, Sun.
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

Wed, Feb 25 - Sun, Mar 1
Multiple Airlines Logo
4:31 pm - 4:16 pm
SJU
-
MDW
25h 45m
2 stops
Multiple Airlines Logo
6:15 am - 2:09 am
MDW
-
SJU
17h 54m
1 stop
$198Multiple Airlines
Thu, May 7 - Sun, May 10
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$202Frontier
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 1:56 pm
SJU
-
MDW
9h 56m
1 stop
Multiple Airlines Logo
6:00 am - 5:58 pm
MDW
-
SJU
10h 58m
1 stop
$206Multiple Airlines
Fri, Feb 27 - Mon, Mar 2
Multiple Airlines Logo
4:16 pm - 10:37 pm
SJU
-
MDW
8h 21m
1 stop
Multiple Airlines Logo
2:19 pm - 6:58 pm
MDW
-
SJU
26h 39m
2 stops
$208Multiple Airlines
Fri, Feb 20 - Thu, Feb 26
Frontier Logo
3:53 am - 2:55 pm
SJU
-
MDW
13h 02m
1 stop
Frontier Logo
7:30 am - 12:43 am
MDW
-
SJU
15h 13m
1 stop
$212Frontier
Fri, May 8 - Mon, May 11
Frontier Logo
3:18 pm - 10:19 pm
SJU
-
MDW
8h 01m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$217Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
4:11 pm - 10:29 pm
SJU
-
MDW
8h 18m
1 stop
Frontier Logo
9:51 pm - 10:12 am
MDW
-
SJU
11h 21m
1 stop
$220Frontier
Wed, Apr 8 - Sun, Apr 12
Frontier Logo
1:11 pm - 10:19 pm
SJU
-
MDW
10h 08m
1 stop
Frontier Logo
9:00 am - 11:18 am
MDW
-
SJU
25h 18m
1 stop
$223Frontier
Wed, Feb 25 - Mon, Mar 2
Frontier Logo
3:53 am - 2:26 pm
SJU
-
MDW
12h 33m
1 stop
Frontier Logo
6:00 am - 3:02 pm
MDW
-
SJU
7h 02m
1 stop
$229Frontier
Wed, Feb 25 - Wed, Mar 11
Frontier Logo
4:06 pm - 4:16 pm
SJU
-
MDW
26h 10m
1 stop
Frontier Logo
6:05 am - 1:19 am
MDW
-
SJU
18h 14m
2 stops
$238Frontier
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 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 $302 (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 $519 respectively.

Good to know

Low seasonFebruary
Cheapest flight$95
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 21% 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 $95 for a one-way ticket and $198 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, 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.
8.0
SouthwestOverall score based on 4280 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

10.0 ExcellentAnonymous, Feb 2026
STL - DAL
Read more Southwest reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

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

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

Information on your arrival and departure airports