$109 Cheap flight deals from Ponce (SJU) to Chicago (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Ponce to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, May 29 - Mon, Jun 1
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$430 Roundtrip, found 5 hours ago
$430
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Fri, May 29 from Luis Munoz Marin Intl. to O'Hare Intl., returning Mon, Jun 1, priced at $430 found 5 hours ago
Sat, May 30 - Mon, Jun 8
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$495 Roundtrip, found 3 days ago
$495
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 30 from Luis Munoz Marin Intl. to Midway Intl., returning Mon, Jun 8, priced at $495 found 3 days ago

Airfares from $109 One Way, $232 Round Trip from Ponce to Chicago

Prices starting at $232 for return flights and $109 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 20 - Mon, Aug 24
SJU
San Juan
ORD
Chicago
$232 Roundtrip, found 4 days ago
$232
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Aug 20 from San Juan to Chicago, returning Mon, Aug 24, priced at $232 found 4 days ago
Fri, Sep 4 - Tue, Sep 8
SJU
San Juan
ORD
Chicago
$235 Roundtrip, found 5 days ago
$235
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Sep 4 from San Juan to Chicago, returning Tue, Sep 8, priced at $235 found 5 days ago
Thu, Sep 3 - Tue, Sep 8
SJU
San Juan
MDW
Chicago
$236 Roundtrip, found 2 days ago
$236
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Sep 3 from San Juan to Chicago, returning Tue, Sep 8, priced at $236 found 2 days ago
Tue, Aug 25 - Fri, Aug 28
SJU
San Juan
ORD
Chicago
$236 Roundtrip, found 17 hours ago
$236
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Aug 25 from San Juan to Chicago, returning Fri, Aug 28, priced at $236 found 17 hours ago
Tue, Aug 25 - Fri, Aug 28
SJU
San Juan
ORD
Chicago
$246 Roundtrip, found 17 hours ago
$246
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Aug 25 from San Juan to Chicago, returning Fri, Aug 28, priced at $246 found 17 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,332 reviews)

Jul 4 - Jul 10

6 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,281, price is now $796 per person
$796
per person
found 1 day ago
Great stay and we highly recommend. We will be back.

Reviewed on Apr 21, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,188 reviews)

Jul 4 - Jul 10

6 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,456, price is now $903 per person
$903
per person
found 1 day ago
Great location, clean, and great breakfast buffet

Reviewed on Mar 8, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (480 reviews)

Jul 4 - Jul 10

6 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,589, price is now $996 per person
$996
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Ponce to Chicago
View all trips

More About Flying To Chicago from Ponce

Route Information for Flights from Ponce to Chicago

Origin Airport IATA Code
SJU
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Ponce to Chicago

Looking for cheap Ponce to Chicago flights? Orbitz has the cheapest air fares for flights from Ponce to Chicago. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

Mobile Deals and Steals

Orbitz is dedicated to providing low fares on Ponce to Chicago flights. Now you can find the latest deals on-the-go with Orbitz’s mobile apps for iPhone, iPad, Android phones, and tablets. Instantly see discounted rates for hotels, cruises, vacations, and air tickets for a great vacation.

Book Hotels With Confidence

When you’re looking for hotel rooms to go with your bargain flights from Ponce to Chicago, Orbitz provides you descriptions, photos, reviews, and location maps so you know exactly what you are booking. With easy-to-use Orbitz map tools, you can search for nearby hotels on your mobile device.

Access Your Flight Information Anytime

Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Ponce to Chicago flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Ponce to Chicago on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Ponce to Chicago flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Chicago. Need hotels too? You can book them last minute on your mobile phone.

Frequently asked questions

Are there non-stop flights from Ponce to Chicago?
United Airlines and American Airlines offer nonstop flights from SJU to Chicago, IL (ORD-O'Hare Intl.), which means you won't need to stress about switching planes or being bored during a layover.
What is the shortest flight from Ponce to Chicago?
The fastest flight from SJU to ORD is 5 hours and 29 minutes. Pack a few things in your carry-on to keep you amused, like a gripping book or your travel journal.
What airlines fly from Ponce to Chicago most frequently?
The carriers that fly frequently between Luis Munoz Marin Intl. Airport (SJU) and O'Hare Intl. Airport (ORD) include United Airlines (UA). This popular option offers 30 flights on the route every month. American Airlines (AA) also services the route from Ponce to Chicago. It's another reliable choice and offers 26 flights every month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.