SJU - ORD

Find cheap flights from San Juan to Chicago

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KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Juan to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Juan to Chicago, as well as popular online travel agencies
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Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flight Deals from San Juan to Chicago (SJU-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from San Juan to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent return flight deals from San Juan to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly from San Juan to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Multiple Airlines Logo
SJU-ORD
2073 mimulti-stop
Multiple Airlines Logo
ORD-SJU
2073 mimulti-stop
Multiple Airlines
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Expert advice

Expert advice for your flight from San Juan to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are specific to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Main Cabin Extra offers early boarding and complimentary drinks, ideal for medium-haul flights.


Download the American Airlines app for in-flight entertainment, as seatback screens may be unavailable.

Read more about American Airlinesby Harriet Baskas
United Airlines

Economy Plus offers 6 inches more legroom than standard economy, enhancing comfort on medium-haul flights.


United's Priority Boarding puts you in Zone 2, ensuring overhead bin space for your carry-on.

Read more about United Airlinesby Stefanie Waldek
Spirit Airlines

Upgrade to Big Front Seat for 20-inch width and 11-inch extra legroom, enhancing comfort.


Spirit's Wi-Fi offers gate-to-gate connectivity, ensuring online access throughout your flight.

Read more about Spirit Airlinesby Joe Cortez
Airports
SJU

San Juan Airport is compact and efficient. For late-night flights, stock up on food as most shops close early.

Read more about SJUby Gabriel Leigh
ORD

Take the CTA Blue Line train from O'Hare to downtown Chicago for a 45-minute ride, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, The Points Guy, and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on SJU

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Useful Info

KAYAK's insights & trends for San Juan to Chicago flights

Get data-powered insights and trends into flights from San Juan to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport is February, where tickets cost £157 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is £275 and £262 respectively.

Can I save money by flying with a stopover from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

The average return price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.
No, with an average price for the route of £645, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.
To get a below average price on the flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.
Find deals

Good to know - Cheap tickets from San Juan to Chicago

Low season

February

High season

July
Best time to beat the crowds (31% less expensive on average)
Most popular time to fly and prices are also 10% lower on average.

When to book flights from San Juan to Chicago

Are your dates flexible? Find out the best times to travel from San Juan to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking San Juan to Chicago flights

  • Which airlines offer Wi-Fi service onboard planes from San Juan to Chicago?

    All the following airlines offer inflight Wi-Fi service on the San Juan to Chicago flight route: American Airlines, Iberia, British Airways, Finnair, Delta, JetBlue, and Alaska Airlines.

  • Which aircraft models fly most regularly from San Juan to Chicago?

    The Boeing 737 MAX 9 is the aircraft model that flies most regularly on the San Juan to Chicago flight route.

  • Which airline alliances offer flights from San Juan to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between San Juan and Chicago, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from San Juan to Chicago?

    There are direct flights from San Juan to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from San Juan to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Juan to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Juan to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Juan is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Juan to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to San Juan with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Juan to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from San Juan up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from San Juan to Chicago?

Find which airlines fly direct from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

San Juan Luis Munoz Marin Intl to Chicago O'Hare Intl

Monday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Tuesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Wednesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Thursday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Friday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Saturday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

See more direct flights

Direct returns

Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl

Monday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Tuesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Wednesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Thursday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Friday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Saturday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

See more direct flights
See more direct flights

Top airline flying from San Juan to Chicago

 
See real verified KAYAK customer reviews for airlines flying from San Juan to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Juan to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.3
Spirit AirlinesOverall score based on 7961 reviews
7.1Crew
5.0Entertainment
6.6Boarding
5.9Comfort
5.1Food
Airline reviews

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

2.0 MediocreAnonymous, Apr 2025LAX - ORD
Read more Spirit Airlines reviews

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

As my first time on Spirit, I thought that it was good.

It was smooth and easy. The only real negative was it took over an hour to get our luggage after the flight

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

Everything you need to know for your flight from San Juan to Chicago

Information on your arrival and departure airports

O'Hare Intl (ORD)
San Juan (SJU)

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