Cheap Flight Tickets from Chicago (MDW) to San Juan (SJU), Starting at $216

Good to Know: Cheapest and Fastest MDW - SJU Flights

Useful information for finding best airline tickets from Chicago Midway International to Luis Munoz Marin International on your next trip.

Cheapest Round Trip Flight

$216

WN Southwest Airlines • 2 stops • 23h 30m

Aug 08 – Aug 16

The cheapest round trip flight from Chicago to San Juan (MDW-SJU-MDW) is currently $216

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Cheapest Direct Flight

$515

F9 Frontier Airlines • nonstop • 8h 20m

Aug 08

The cheapest nonstop flight from Chicago to San Juan (MDW-SJU) is currently $515

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Fastest Flight

7h 35m

The fastest nonstop flight from Chicago to San Juan (MDW-SJU) takes 7h 35m

Top Airlines Flying from Chicago to San Juan

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Latest Flight Deals from Chicago (MDW) to San Juan (SJU)

Compare and book low fare round-trip air tickets from Chicago to San Juan. Ideal for travelers with confirmed return itineraries.

Aug 08 - Aug 16, Economy
WN
Chicago → San Juan
23h 30m
6:00 PM - 9:10 AM • 2 stops
WN
Chicago → San Juan
20h 20m
9:25 PM - 8:45 AM • 1 stop
$216
Southwest Airlines
Aug 08 - Aug 16, Economy
WN
Chicago → San Juan
20h 55m
8:00 AM - 9:55 PM • 2 stops
WN
Chicago → San Juan
20h 20m
11:35 AM - 10:55 PM • 2 stops
$311
Southwest Airlines
Aug 08 - Aug 16, Economy
WN
Chicago → San Juan
18h 40m
5:55 AM - 6:15 PM • 2 stops
WN
Chicago → San Juan
21h 55m
11:35 AM - 11:50 PM • 2 stops
$322
Southwest Airlines
Aug 08 - Aug 16, Economy
WN
Chicago → San Juan
21h 55m
7:40 AM - 9:55 PM • 2 stops
WN
Chicago → San Juan
22h 15m
9:25 PM - 10:00 AM • 1 stop
$557
Southwest Airlines
Aug 08 - Aug 16, Economy
UA
Chicago → San Juan
7h 36m
2:38 PM - 8:34 PM • nonstop
AA
Chicago → San Juan
21h 50m
7:24 PM - 7:34 AM • 1 stop
$655
United Airlines
Aug 08 - Aug 16, Economy
WN
Chicago → San Juan
21h 45m
7:50 AM - 9:55 PM • 2 stops
WN
Chicago → San Juan
20h 20m
9:25 PM - 8:45 AM • 1 stop
$701
Southwest Airlines

Fly from Chicago to San Juan with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to San Juan? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to San Juan Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to SJU?
The most popular airline flying from Chicago to San Juan are
Can I fly from MDW to SJU non-stop?
Yes, you can fly MDW to SJU non-stop on
Which airlines fly nonstop between Chicago and San Juan?
The non-stop flights between Chicago and San Juan are .
What’s the earliest departure time from MDW to SJU Airport?
The earliest flight leaves MDW at 12:44 am and lands in SJU - Luis Munoz Marin International
What are the airports in San Juan?
SJU
Can I make changes to my Chicago to San Juan flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to SJU?
Read the fare rules of the Chicago to San Juan air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and San Juan?
operate flights between Chicago and San Juan
How long does a flight from Chicago to San Juan take?
It takes approximately 5 hour to fly non-stop from MDW to SJU, which is 2056.77 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to San Juan (SJU) ?
In the past couple of days, the cheapest tickets to SJU from MDW were found on WN : USD 216
Do I need a passport to fly between MDW and SJU?
Yes
What’s the latest departure time from MDW to SJU ?
The last flight leaves MDW at 6:00 pm

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw to sju?
You can find affordable business class flights from Chicago Midway International Airport (mdw) to Luis Munoz Marin International Airport (sju) on Southwest Airlines. For a round-trip journey, consider booking at least 11 days in advance for the best low fares. With three passengers, you'll enjoy premium service with priority, lounge access, and flatbed seats.
What's the popular airline to fly from mdw to sju?
For a round-trip Business class flight from Chicago Midway International Airport (mdw) to Luis Munoz Marin International Airport (sju), consider booking with Southwest Airlines for its premium service, which includes priority check-in, lounge access, and flatbed seats. This option is available on the airline's website.
What's the cheapest day of the week to fly from mdw to sju?
The cheapest day to fly from Chicago Midway International Airport (mdw) to Luis Munoz Marin International Airport (sju) is Friday. Flying on Fridays can help you save money on airfares, as it's often the cheapest day of the week for flights. You can find budget-friendly flights with airlines offering low fares and savings.
What's the cheapest month to fly from mdw to sju?
The cheapest month to fly from Chicago Midway International Airport (mdw) to Luis Munoz Marin International Airport (sju) is October. You can find budget-friendly flights during this time, making it a great option for your round-trip business class journey.
Which airline/airlines fly from mdw to sju?
The airlines that fly from Chicago Midway International Airport (mdw) to Luis Munoz Marin International Airport (sju) include United Airlines, WestJet Airlines, Southwest Airlines, Volaris Airline, JetBlue Airways, Delta Airlines, Porter Airline, Frontier Airlines, Allegiant, and American Airlines. You can find the most up-to-date information on airfare prices and schedules for these airlines on their official websites or through a travel agency.
What is the best time to book flights from Milwaukee to San Juan for the cheapest airfare?
For the most affordable airfare, it's recommended to book your flight from Milwaukee to San Juan at least 11 days in advance, with October being the cheapest month to travel.
How can I find the most affordable airline tickets for my round trip journey from Chicago to Luis Munoz Marin International Airport?
Southwest Airlines is a great option for finding affordable airfare on your round trip journey from Chicago to San Juan. They offer competitive prices and convenient flight schedules.
Can you recommend an agency or website that offers great deals on airflights and travel packages to Rico?
FareLeaders is a fantastic resource for finding amazing deals on airflights and travel packages to Rico. Their website offers a wide range of options and competitive pricing.
What are some tips for booking flights with advance notice, like 11 days before departure?
Booking flights with advance notice can help you secure the best prices. It's recommended to book at least 11 days in advance to get the cheapest airfare.
How can I ensure I get the best business class seats with priority service on my flight from Chicago Midway International Airport to San Juan?
To ensure you get the best business class seats with priority service, it's recommended to book a premium cabin and select your seat in advance. Southwest Airlines offers competitive pricing for their business class seats.
Are there any special offers or discounts available for travelers planning their trip in July?
Yes, there are several special offers and discounts available for travelers planning their trip in July. Be sure to check the airlines' websites and FareLeaders for the latest deals.

Chicago (MDW) to San Juan (SJU): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport Luis Munoz Marin International , San Juan, PR
Distance 2057 miles

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