Cheap Flight Tickets from San Juan (SJU) to Chicago (MDW), Starting at $136

Good to Know: Cheapest and Fastest SJU - MDW Flights

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

Cheapest Round Trip Flight

$271

WN Southwest Airlines • 2 stops • 15h 40m

Dec 20 – Dec 27

The cheapest round trip flight from San Juan to Chicago (SJU-MDW-SJU) is currently $271

🔍 Search Flights

Cheapest Direct Flight

$450

F9 Frontier Airlines • nonstop • 8h 27m

Dec 23

The cheapest nonstop flight from San Juan to Chicago (SJU-MDW) is currently $450

🔍 Search Flights

Fastest Flight

8h 27m

The fastest nonstop flight from San Juan to Chicago (SJU-MDW) takes 8h 27m

Top Airlines Flying from San Juan to Chicago

Southwest Airlines-WN

Southwest Airlines

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

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

Dec 20 - Dec 27, Economy
WN
San Juan → Chicago
15h 40m
6:05 AM - 1:45 PM • 2 stops
WN
San Juan → Chicago
10h 25m
8:50 AM - 5:15 PM • 1 stop
$271
Southwest Airlines
Dec 20 - Dec 27, Economy
WN
San Juan → Chicago
14h 5m
5:35 AM - 12:20 PM • 1 stop
WN
San Juan → Chicago
10h 55m
4:50 PM - 1:45 AM • 1 stop
$271
Southwest Airlines
Dec 20 - Dec 27, Economy
WN
San Juan → Chicago
13h 50m
5:35 AM - 12:05 PM • 2 stops
WN
San Juan → Chicago
12h 20m
9:15 AM - 6:55 PM • 2 stops
$271
Southwest Airlines
Dec 20 - Dec 27, Economy
WN
San Juan → Chicago
13h 50m
5:35 AM - 12:05 PM • 1 stop
WN
San Juan → Chicago
20h 35m
9:45 AM - 12:20 AM • 2 stops
$550
Southwest Airlines
Dec 20 - Dec 27, Economy
WN
San Juan → Chicago
18h 35m
6:35 AM - 3:50 PM • 1 stop
WN
San Juan → Chicago
20h 35m
9:45 AM - 12:20 AM • 2 stops
$550
Southwest Airlines
Dec 20 - Dec 27, Economy
WN
San Juan → Chicago
19h 15m
5:35 AM - 3:30 PM • 1 stop
WN
San Juan → Chicago
14h
3:05 PM - 1:45 AM • 1 stop
$702
Southwest Airlines

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

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

FAQs on San Juan to Chicago Flights

What are the airports in San Juan?
SJU
What’s the most popular airline flying from SJU to MDW?
The most popular airline flying from San Juan to Chicago are
Can I fly from SJU to MDW non-stop?
Yes, you can fly SJU to MDW non-stop on
Which airlines fly nonstop between San Juan and Chicago?
The non-stop flights between San Juan and Chicago are .
What’s the earliest departure time from SJU to MDW Airport?
The earliest flight leaves SJU at 5:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Juan to Chicago 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 SJU to MDW?
Read the fare rules of the San Juan to Chicago 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 San Juan and Chicago?
operate flights between San Juan and Chicago
How long does a flight from San Juan to Chicago take?
It takes approximately 5 hour to fly non-stop from SJU to MDW, which is 2056.77 miles by air.
Which airlines provide the cheapest flights from San Juan (SJU) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SJU were found on WN : USD 271
Do I need a passport to fly between SJU and MDW?
Yes
What’s the latest departure time from SJU to MDW ?
The last flight leaves SJU at 10:2600 pm

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

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

More Flight Options for San Juan (SJU) and Chicago (MDW)

Why Fareleaders for SJU to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on San Juan to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on SJU to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of San Juan to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the San Juan (SJU) to Chicago (MDW)
Terms and Conditions*