Cheap Flight Tickets from San Juan (SJU) to Chicago (ORD), Starting at $257

Good to Know: Cheapest and Fastest SJU - ORD Flights

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

Cheapest Round Trip Flight

$428

F9 Frontier Airlines • 1 stop • 19h 2m

Oct 29 – Oct 29

The cheapest round trip flight from San Juan to Chicago (SJU-ORD-SJU) is currently $428

🔍 Search Flights

Cheapest One way Flight

$257

B6 JetBlue Airways • 2 stops • 42h

Oct 28

The cheapest one way flight from San Juan to Chicago (SJU-ORD) is currently $257

🔍 Search Flights

Cheapest Direct Flight

$541

UA United Airlines • nonstop • 8h 44m

Oct 29

The cheapest nonstop flight from San Juan to Chicago (SJU-ORD) is currently $541

🔍 Search Flights

Fastest Flight

8h 44m

The fastest nonstop flight from San Juan to Chicago (SJU-ORD) takes 8h 44m

Top Airlines Flying from San Juan to Chicago

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

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

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

Oct 29 - Oct 29, Economy
F9
San Juan → Chicago
19h 2m
1:59 AM - 12:41 PM • 1 stop
F9
San Juan → Chicago
13h 26m
4:44 PM - 1:50 AM • 1 stop
$428
Frontier Airlines
Oct 29 - Nov 02, Economy
DL
San Juan → Chicago
17h 28m
7:15 AM - 5:03 PM • 1 stop
DL
San Juan → Chicago
14h 14m
1:50 PM - 12:44 AM • 1 stop
$466
Delta Airlines
Oct 29 - Nov 02, Economy
UA
San Juan → Chicago
12h 29m
4:50 PM - 11:39 PM • 1 stop
UA
San Juan → Chicago
13h 26m
2:30 PM - 12:36 AM • 1 stop
$556
United Airlines
Oct 29 - Oct 29, Economy
AA
San Juan → Chicago
22h 15m
6:00 AM - 6:35 PM • 1 stop
AA
San Juan → Chicago
28h 26m
8:55 PM - 3:01 PM • 1 stop
$580
American Airlines
Oct 29 - Oct 29, Economy
AA
San Juan → Chicago
16h 40m
6:00 AM - 3:00 PM • 1 stop
AA
San Juan → Chicago
22h 5m
8:55 PM - 11:20 AM • 1 stop
$586
American Airlines
Oct 29 - Oct 29, Economy
AA
San Juan → Chicago
16h 53m
6:20 AM - 3:33 PM • 1 stop
AA
San Juan → Chicago
22h 5m
8:55 PM - 11:20 AM • 1 stop
$647
American 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 ORD?
The most popular airline flying from San Juan to Chicago are
Can I fly from SJU to ORD non-stop?
Yes, you can fly SJU to ORD 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 ORD Airport?
The earliest flight leaves SJU at 1:59 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
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 ORD?
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 ORD, which is 2071.72 miles by air.
Which airlines provide the cheapest flights from San Juan (SJU) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from SJU were found on B6 : USD 317
Do I need a passport to fly between SJU and ORD?
Yes
What’s the latest departure time from SJU to ORD ?
The last flight leaves SJU at 4:50 pm

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

Origin Airport Luis Munoz Marin International , San Juan, PR
Destination Airport Chicago O'Hare International , Chicago, US
Distance 2072 miles

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

Why Fareleaders for SJU to ORD 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 ORD 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 (ORD)
Terms and Conditions*