Cheap Flight Tickets from Chicago (MDW) to San Juan (SJU), Starting at $507

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

$507

WN Southwest Airlines • 2 stops • 15h 10m

Jul 18 – Jul 27

The cheapest round trip flight from Chicago to San Juan (MDW-SJU-MDW) is currently $507

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Cheapest Direct Flight

$804

WN Southwest Airlines • nonstop • 7h 20m

Jul 19

The cheapest nonstop flight from Chicago to San Juan (MDW-SJU) is currently $804

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Fastest Flight

7h 20m

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

Jul 18 - Jul 27, Economy
WN
Chicago → San Juan
15h 10m
12:55 PM - 11:05 PM • 2 stops
WN
Chicago → San Juan
19h
10:20 PM - 9:00 AM • 1 stop
$507
Southwest Airlines
Jul 18 - Jul 27, Economy
WN
Chicago → San Juan
13h 55m
12:50 PM - 10:25 PM • 2 stops
WN
Chicago → San Juan
20h 30m
10:20 PM - 9:50 AM • 1 stop
$507
Southwest Airlines
Jul 18 - Jul 27, Economy
WN
Chicago → San Juan
15h 15m
12:50 PM - 11:05 PM • 2 stops
WN
Chicago → San Juan
20h 30m
10:20 PM - 9:50 AM • 1 stop
$507
Southwest Airlines
Jul 19 - Jul 26, Economy
WN
Chicago → San Juan
18h 20m
6:10 AM - 6:10 PM • 1 stop
WN
Chicago → San Juan
18h 40m
5:00 AM - 3:20 PM • 2 stops
$510
Southwest Airlines
Jul 19 - Jul 26, Economy
WN
Chicago → San Juan
25h 10m
7:45 AM - 11:55 PM • 2 stops
WN
Chicago → San Juan
18h 40m
5:00 AM - 3:20 PM • 2 stops
$564
Southwest Airlines
Jul 20 - Jul 25, Economy
WN
Chicago → San Juan
15h 30m
11:00 AM - 9:30 PM • 1 stop
WN
Chicago → San Juan
7h 30m
5:30 AM - 9:20 AM • nonstop
$575
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 6:10 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 575
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 12:55 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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