$154 Cheap Flights from San Juan (SJU) to Chicago (MDW)

View $154 flight on Wed, Oct 1, 2025Opens in a new window

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

Find available prices by choosing your travel dates.

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

Prices were available within the past 7 days and start at $154 for one-way flights and $307 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 1 - Thu, Oct 2
SJU
San Juan
MDW
Chicago
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 1 from San Juan to Chicago, returning Thu, Oct 2, priced at $307 found 2 days ago
Frontier Airlines
Fri, May 2 - Mon, May 5
SJU
San Juan
MDW
Chicago
$308 Roundtrip, just found
$308
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 2 from San Juan to Chicago, returning Mon, May 5, priced at $308 just found
Frontier Airlines
Fri, May 2 - Mon, May 5
SJU
San Juan
MDW
Chicago
$318 Roundtrip, just found
$318
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 2 from San Juan to Chicago, returning Mon, May 5, priced at $318 just found
Frontier Airlines
Wed, May 14 - Thu, May 15
SJU
San Juan
MDW
Chicago
$328 Roundtrip, found 3 days ago
$328
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 14 from San Juan to Chicago, returning Thu, May 15, priced at $328 found 3 days ago
Frontier Airlines
Thu, Jun 5 - Mon, Jun 9
SJU
San Juan
MDW
Chicago
$328 Roundtrip, found 2 hours ago
$328
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jun 5 from San Juan to Chicago, returning Mon, Jun 9, priced at $328 found 2 hours ago
Frontier Airlines
Wed, May 21 - Mon, Jun 2
SJU
San Juan
MDW
Chicago
$335 Roundtrip, found 2 days ago
$335
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 21 from San Juan to Chicago, returning Mon, Jun 2, priced at $335 found 2 days ago
Frontier Airlines
Wed, May 21 - Thu, Jun 5
SJU
San Juan
MDW
Chicago
$337 Roundtrip, found 2 days ago
$337
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 21 from San Juan to Chicago, returning Thu, Jun 5, priced at $337 found 2 days ago
Frontier Airlines
Wed, Apr 30 - Thu, May 15
SJU
San Juan
MDW
Chicago
$338 Roundtrip, found 8 hours ago
$338
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Apr 30 from San Juan to Chicago, returning Thu, May 15, priced at $338 found 8 hours ago
Delta
Fri, Sep 12 - Thu, Sep 18
SJU
San Juan
MDW
Chicago
$342 Roundtrip, found 6 days ago
$342
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 12 from San Juan to Chicago, returning Thu, Sep 18, priced at $342 found 6 days ago
Southwest Airlines
Sat, May 24 - Wed, May 28
SJU
San Juan
MDW
Chicago
$350 Roundtrip, found 6 hours ago
$350
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, May 24 from San Juan to Chicago, returning Wed, May 28, priced at $350 found 6 hours ago

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 $312 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 May 10 2025 and touching down at MDW. The price was last updated on April 23 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 $231. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SJU on May 3 2025. Prices were last updated on April 23 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.
*Available to One Key members.