$117 Cheap Flights from San Juan (SJU) to Chicago (MDW)

View $117 flight on Fri, Sep 5, 2025Opens in a new window

Popular airlines from Luis Munoz Marin Intl. Airport (SJU) to Chicago Midway Airport (MDW)

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Cheap Flights from San Juan to Chicago (SJU-MDW)

Prices were available within the past 7 days and start at $117 for one-way flights and $233 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Sep 11 - Mon, Sep 15
SJU
San Juan
MDW
Chicago
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Sep 11 from San Juan to Chicago, returning Mon, Sep 15, priced at $233 found 1 day ago
Delta
Fri, Sep 5 - Sun, Sep 7
SJU
San Juan
MDW
Chicago
$233 Roundtrip, just found
$233
Roundtrip
just found
Select Delta flight, departing Fri, Sep 5 from San Juan to Chicago, returning Sun, Sep 7, priced at $233 just found
Frontier Airlines
Fri, Sep 5 - Sun, Sep 7
SJU
San Juan
MDW
Chicago
$260 Roundtrip, just found
$260
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 5 from San Juan to Chicago, returning Sun, Sep 7, priced at $260 just found
Southwest Airlines
Thu, Sep 4 - Mon, Sep 8
SJU
San Juan
MDW
Chicago
$263 Roundtrip, found 7 hours ago
$263
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from San Juan to Chicago, returning Mon, Sep 8, priced at $263 found 7 hours ago
Southwest Airlines
Fri, Sep 5 - Sun, Sep 7
SJU
San Juan
MDW
Chicago
$264 Roundtrip, just found
$264
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Sep 5 from San Juan to Chicago, returning Sun, Sep 7, priced at $264 just found
Frontier Airlines
Fri, Sep 19 - Sun, Sep 28
SJU
San Juan
MDW
Chicago
$272 Roundtrip, found 1 day ago
$272
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 19 from San Juan to Chicago, returning Sun, Sep 28, priced at $272 found 1 day ago
Frontier Airlines
Fri, Aug 29 - Sun, Sep 7
SJU
San Juan
MDW
Chicago
$274 Roundtrip, found 9 hours ago
$274
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, Aug 29 from San Juan to Chicago, returning Sun, Sep 7, priced at $274 found 9 hours ago
Frontier Airlines
Wed, Aug 6 - Mon, Aug 25
SJU
San Juan
MDW
Chicago
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Aug 6 from San Juan to Chicago, returning Mon, Aug 25, priced at $274 found 2 days ago
Southwest Airlines
Fri, Sep 5 - Sun, Sep 7
SJU
San Juan
MDW
Chicago
$280 Roundtrip, just found
$280
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Sep 5 from San Juan to Chicago, returning Sun, Sep 7, priced at $280 just found
Southwest Airlines
Thu, Sep 18 - Tue, Sep 23
SJU
San Juan
MDW
Chicago
$282 Roundtrip, found 3 days ago
$282
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Sep 18 from San Juan to Chicago, returning Tue, Sep 23, priced at $282 found 3 days ago

Find the cheapest month to fly from San Juan (SJU) to Chicago (MDW)

September is typically the cheapest month to fly

From $138 - $644 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $246
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $246
Flights from San Juan (SJU) to Chicago (MDW)
Origin airport
Luis Munoz Marin Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$233
Distance
2058 mi
Average flight time
4 hours 57 mins

San Juan to Chicago Flights

The cheapest times to fly from San Juan to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from San Juan to Chicago are during the month of September. You can find some of the cheapest flights from San Juan to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from San Juan to Chicago

Sunday is one of the best days to book for cheap flights from San Juan to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from San Juan to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from San Juan to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $117 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap San Juan to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your San Juan to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW) cost?
Snag cheap return fares starting at $411 from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving SJU on July 20 2025 and touching down at MDW. The price was last updated on July 11 2025 and has not changed since.
What is the cheapest month to fly from SJU to MDW?
The cheapest flights from SJU to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
Fly nonstop from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from SJU to MDW?
At the moment, the cheapest airline operating one-way flights from SJU to MDW is Southwest Airlines. You can take off on this route from $282. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJU on August 2 2025. Prices were last updated on July 11 2025 and have not changed since.
How many flights per day from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
On average you can take your pick of 1 direct flights per week from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW). To broaden your travel options, consider taking a flight with a layover. Simply enter your dates on Expedia and then set the filter tool to include one or more stops.
What are the most popular departure times for flights from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
Flights between SJU and MDW are busiest at 2 PM. If you'd like a quieter experience and potentially cheaper prices, look for a departure that's outside typical rush times.
What day of the week has the most flights from SJU to MDW?
Depart on a Saturday if you're after the biggest selection of flights from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW).
What is the earliest flight from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
The earliest flight jetting off from Luis Munoz Marin Intl. Airport (SJU) is at around 2:55PM UTC-4. Catch this flight and you'll touch down at Midway Intl. Airport (MDW) at approximately 6:10PM UTC-6. The entire trip takes 5h 15m.
How long does it take to fly from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
Flights from SJU to MDW have an average travel time of 5 hours and 15 minutes. The total distance between the two is 2,100 mi.
What is the best time to fly from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
Book a flight from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the risk of delays and cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Luis Munoz Marin Intl. Airport (SJU)?
You can arrive at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when traveling to Chicago on a direct flight from Luis Munoz Marin Intl. Airport (SJU).
Is it cheaper to buy a plane ticket from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from SJU to MDW shortly before your trip is generally more expensive. But if there's some wiggle room with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book a SJU to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a SJU to MDW flight and hotel package with Expedia could lead to significant savings. What's more, having everything in one convenient place will take the hassle out of travel planning. Just pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
Typically, you're able to cancel or reschedule your SJU to MDW flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like further details, go to our Customer Service portal.

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