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

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This Weekend's Flight Deals from San Juan 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.

Sat, Jun 21 - Tue, Jun 24
SJU
Luis Munoz Marin Intl.
ORD
O'Hare Intl.
$271 Roundtrip, just found
$271
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 21 from Luis Munoz Marin Intl. to O'Hare Intl., returning Tue, Jun 24, priced at $271 just found
Sat, Jun 21 - Sun, Jul 20
SJU
Luis Munoz Marin Intl.
MDW
Midway Intl.
$314 Roundtrip, found 2 hours ago
$314
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Luis Munoz Marin Intl. to Midway Intl., returning Sun, Jul 20, priced at $314 found 2 hours ago

Airfares from $109 One Way, $221 Round Trip from San Juan to Chicago

Prices starting at $221 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.

Fri, Jun 27 - Tue, Jul 8
SJU
San Juan
ORD
Chicago
$221 Roundtrip, found 4 days ago
$221
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Jun 27 from San Juan to Chicago, returning Tue, Jul 8, priced at $221 found 4 days ago
Tue, Jul 15 - Tue, Jul 22
SJU
San Juan
ORD
Chicago
$223 Roundtrip, just found
$223
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jul 15 from San Juan to Chicago, returning Tue, Jul 22, priced at $223 just found
Thu, Sep 25 - Mon, Sep 29
SJU
San Juan
MDW
Chicago
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Sep 25 from San Juan to Chicago, returning Mon, Sep 29, priced at $240 found 1 day ago
Thu, Jun 26 - Mon, Jun 30
SJU
San Juan
ORD
Chicago
$240 Roundtrip, just found
$240
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jun 26 from San Juan to Chicago, returning Mon, Jun 30, priced at $240 just found
Wed, Jul 9 - Wed, Jul 16
SJU
San Juan
ORD
Chicago
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jul 9 from San Juan to Chicago, returning Wed, Jul 16, priced at $277 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (1,759 reviews)

Jul 19 - Jul 26

7 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Great location for doing things downtown. Walkable to every where one wants to go, or a cheap Lyft ride.

Reviewed on May 1, 2025

Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

8/10 Very Good! (8,858 reviews)

Jul 19 - Jul 26

7 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
It’s was easy- we were in our rooms within a Few minutes of arriving

Reviewed on Jun 1, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

8.8/10 Excellent! (1,771 reviews)

Jul 19 - Jul 26

7 night stay

San Juan (SJU) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to San Juan (SJU)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Attitude of the people was outstanding!! Very friendly and helpful.

Reviewed on Jun 13, 2025

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More About Flying To Chicago from San Juan

Route Information for Flights from San Juan to Chicago

Origin Airport IATA Code
SJU
Destination Airport IATA Code
CHI
Distance
2073 mi
Direct Flight Airlines
American Airlines, Air Canada, Alaska Airlines, Air New Zealand, United Airlines, Spirit Airlines
Earliest Flight Arrival
3:06PM UTC
Latest Flight Arrival
12:15AM UTC

San Juan to Chicago

San Juan to Chicago flights are offered at fantastic discount by Orbitz. Book air tickets now and cut those extra costs out of your travel budget to ensure a rewarding travel experience. With guaranteed low prices like these, can you afford to miss this discount?

Book cheap flights from San Juan to Chicago

Cheap airfares are available on flights from San Juan to Chicago. Use Orbitz to find the best flights that suit both your budget and the travel times that you need. Travelers who are looking for discounted rates on domestic or international flights need to look no further than Orbitz.

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As the world of technology rapidly expands around us, we are continuously finding new ways to improve our services, communications, and accessibility. With our cutting-edge mobile tools now available on Android, iPhone, and tablets, you can access detailed information on your bookings for flights from San Juan to Chicago at any time or anywhere. See your itinerary for your San Juan to Chicago flights, baggage and gate claim details, as well as hotel deals with our easy-to-use apps.

Get a great package with your San Juan to Chicago flights

With frequent updates on your flight status, including delays and changes in bookings, traveling becomes more hassle-free than ever. Not only do we offer huge discounted deals on flights from San Juan to Chicago, we also have fantastic savings on vacation packages, hotel room, cruises, activities, and car rentals so you can pick and choose and create the best travel package for you.

Frequently asked questions

Are there non-stop flights from San Juan to Chicago?
There are, which is excellent news if you’re not a big fan of swapping planes en route. United Airlines and American Airlines fly straight from Luis Munoz Marin Intl. Airport (SJU) to O’Hare Intl. Airport (ORD).
What is the shortest flight from San Juan to Chicago?
The fastest flight time from San Juan to Chicago is 5 hours and 29 minutes, which gives you lots of time to enjoy a beverage or lose yourself in a good book.
What airlines fly from San Juan to Chicago most frequently?
Have a look at United Airlines (UA). This airline offers some of the most frequent flights from San Juan (SJU-Luis Munoz Marin Intl.) to ORD. It operates 30 services on this route every month and is a favorite with travelers. American Airlines (AA) also operates services from San Juan to Chicago. It’s another great option and has 26 flights each 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.

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.