$114 Cheap Flights from San Juan (SJU) to Chicago (MDW)

View $114 flight on Fri, Jan 30, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $114 for one-way flights and $179 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Dec 24 - Thu, Jan 8
SJU
San Juan
MDW
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Thu, Jan 8, priced at $179 found 2 days ago
Frontier Airlines
Wed, Dec 24 - Wed, Jan 7
SJU
San Juan
MDW
Chicago
$198 Roundtrip, found 9 hours ago
$198
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Wed, Jan 7, priced at $198 found 9 hours ago
Frontier Airlines
Thu, Jan 15 - Mon, Jan 26
SJU
San Juan
MDW
Chicago
$204 Roundtrip, found 5 days ago
$204
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jan 15 from San Juan to Chicago, returning Mon, Jan 26, priced at $204 found 5 days ago
Frontier Airlines
Wed, Dec 24 - Wed, Dec 31
SJU
San Juan
MDW
Chicago
$206 Roundtrip, found 2 days ago
$206
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Wed, Dec 31, priced at $206 found 2 days ago
Frontier Airlines
Wed, Dec 24 - Wed, Jan 7
SJU
San Juan
MDW
Chicago
$208 Roundtrip, found 9 hours ago
$208
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Wed, Jan 7, priced at $208 found 9 hours ago
Frontier Airlines
Wed, Dec 24 - Wed, Jan 7
SJU
San Juan
MDW
Chicago
$212 Roundtrip, found 9 hours ago
$212
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Dec 24 from San Juan to Chicago, returning Wed, Jan 7, priced at $212 found 9 hours ago
Frontier Airlines
Thu, Jan 15 - Sun, Jan 18
SJU
San Juan
MDW
Chicago
$213 Roundtrip, found 16 hours ago
$213
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, Jan 15 from San Juan to Chicago, returning Sun, Jan 18, priced at $213 found 16 hours ago
Frontier Airlines
Thu, Jan 15 - Mon, Jan 19
SJU
San Juan
MDW
Chicago
$225 Roundtrip, found 3 days ago
$225
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jan 15 from San Juan to Chicago, returning Mon, Jan 19, priced at $225 found 3 days ago
Delta
Fri, Jan 23 - Mon, Jan 26
SJU
San Juan
MDW
Chicago
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jan 23 from San Juan to Chicago, returning Mon, Jan 26, priced at $227 found 3 days ago
Southwest Airlines
Fri, Jan 30 - Mon, Feb 2
SJU
San Juan
MDW
Chicago
$227 Roundtrip, just found
$227
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Jan 30 from San Juan to Chicago, returning Mon, Feb 2, priced at $227 just found

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

February is typically the cheapest month to fly

From $140 - $720 per traveler.

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. Average driving time to city center is 23 minutes. Flights from $437
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $437
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
$178
Distance
2058 mi

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 December. 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 $114 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?
Get a cheap one-way flight from $114 or cheap return flight from $179 from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
December is the cheapest month to fly from SJU to MDW. Timing your trip outside of the busy season is often the key to finding better fares.
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 Luis Munoz Marin Intl. Airport (SJU) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from SJU to MDW, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
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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*Available to One Key members.