$74 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.

Airfares from $74 One Way, $168 Round Trip from San Juan to Chicago

Prices starting at $168 for return flights and $74 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.

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Hotel Riu Plaza Chicago
The Emily Hotel
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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

San Juan to Chicago

It can be tedious to sift through pages of Internet search results to find those bargain fares on flights from San Juan to Chicago and hotels, but at Orbitz, everything you need is in one place. Our guaranteed low prices on San Juan to Chicago flights mean we are a leader when it comes to giving you great online deals on air fare and hotels.

Huge savings with little effort

Whether you are traveling for pleasure or business, you can use Orbitz to find cheap San Juan to Chicago flights, together with low-cost accommodations. We pride ourselves on offering you excellent deals that fit your schedule and budget needs.

Unbeatable low fare flights from San Juan to Chicago

Domestic or international travel presents no obstacles to us. We give you unbeatable bargains on flights from San Juan to Chicago. Enjoy huge savings on your flight, which can be better used elsewhere on your trip.

Grab that cheap deal on the move

Our innovative and cutting-edge mobile tools make it easy to search or booking cheap flights from San Juan to Chicago while on the move, via our app for the iPhone, iPad, or Android-based devices. We can also send you instant alerts through email or text messaging if there any delays to your flight.

Orbitz means low-cost trip-planning made easy

Low-cost San Juan to Chicago flights can be booked with total confidence through Orbitz every time. We also make it very easy to cancel flights or other travel arrangements online should you need to. You can also add activities and car rentals to your flight or hotel reservation for a hassle-free trip.

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.

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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.