Cheap Flight Tickets from Chicago (MDW) to San Juan (SJU), Starting at $206

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

$539

WN Southwest Airlines • 1 stop • 21h 40m

Apr 09 – Apr 17

The cheapest round trip flight from Chicago to San Juan (MDW-SJU-MDW) is currently $539

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Fastest Flight

10h 20m

The fastest nonstop flight from Chicago to San Juan (MDW-SJU) takes 10h 20m

Top Airlines Flying from Chicago to San Juan

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta 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.

Apr 09 - Apr 17, Economy
WN
Chicago → San Juan
21h 40m
8:10 AM - 10:10 PM • 1 stop
WN
Chicago → San Juan
10h 55m
4:15 PM - 10:10 PM • 1 stop
$539
Southwest Airlines
Apr 09 - Apr 17, Economy
WN
Chicago → San Juan
13h 50m
2:20 PM - 11:50 PM • 2 stops
WN
Chicago → San Juan
10h 55m
4:15 PM - 10:10 PM • 1 stop
$539
Southwest Airlines
Apr 09 - Apr 17, Economy
WN
Chicago → San Juan
20h 35m
8:40 AM - 10:15 PM • 1 stop
WN
Chicago → San Juan
10h 55m
4:15 PM - 10:10 PM • 1 stop
$570
Southwest Airlines
Apr 09 - Apr 17, Economy
WN
Chicago → San Juan
13h 45m
5:25 AM - 2:50 PM • 1 stop
WN
Chicago → San Juan
10h 55m
4:15 PM - 10:10 PM • 1 stop
$580
Southwest Airlines
Apr 09 - Apr 17, Economy
WN
Chicago → San Juan
13h 20m
7:00 AM - 4:00 PM • 1 stop
WN
Chicago → San Juan
8h 30m
1:15 PM - 5:25 PM • nonstop
$581
Southwest Airlines
Apr 09 - Apr 17, Economy
WN
Chicago → San Juan
12h 15m
1:35 PM - 10:10 PM • 1 stop
WN
Chicago → San Juan
8h 30m
1:15 PM - 5:25 PM • nonstop
$586
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?
NO
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 5:00 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 580
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 2:40 pm

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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