$75 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 $75 One Way, $150 Round Trip from San Juan to Chicago

Prices starting at $150 for return flights and $75 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.
theWit Chicago, a Hilton Hotel
Hotel Riu Plaza Chicago
Chicago Athletic Association, a Hyatt 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

For the best available deals on flights from San Juan to Chicago, look no further than Orbitz. Offering the perfect packages with cutting-edge mobile tools, Orbitz is your ideal destination.

One Stop Travel Shop

Not only is Orbitz the best source for great deals on flights from San Juan to Chicago, we offer the complete package. From guaranteed low prices on hotels, car rentals and activities, simply decide what you want and Orbitz will put together the complete vacation package.

Searching Anywhere

Booking San Juan to Chicago flights is simple, wherever you are. Book on your computer and the Orbitz Display Matrix gives all your deals and discounts on flights from San Juan to Chicago, showing your great savings. Or if you are on the move, use m.orbitz.com on your mobile browser to find exclusive San Juan to Chicago flights for mobile users.

Worry-free Travel Planning

Orbitz is the best place for San Juan to Chicago flights at guaranteed low prices, we also take the stress out of your flight details. With our free alerts service you can quickly find out your gate number or flight delays via email or text – perfect if you are in a rush.

Miles Better

If you frequently travel on flights from San Juan to Chicago, it’s easy to rack up your air miles. Just add your frequent flyer number when booking your flights and we will do the rest. Orbitz will even store your number in your profile to automatically add on your miles each time you book.

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.