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SJU - ORD

Find cheap flights from San Juan to Chicago

1 adult
0 bags
Wed 29/5
Wed 5/6

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days, travellers have searched 43,983,279 times on KAYAK, and here's why:

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Flights from San Juan to Chicago - Travel Insights & Trends

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’s the cheapest day of the week to fly from San Juan to Chicago?

The average price of all flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
For San Juan to Chicago, Sunday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago back to San Juan, the best deals are generally found on Monday, with Wednesday being the most expensive.

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 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 September, where tickets cost £185 on average. On the other hand, the most expensive months are April and March, where the average cost of tickets is £387 and £378 respectively.

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 daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
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 1 week before departure. For the absolute cheapest price, our data suggests you should book 63 days before departure.

Which airlines fly most frequently between San Juan and Chicago?

American Airlines connects San Juan to Chicago with up to 1 flight per day and both Spirit Airlines and United Airlines also offer 1 flight per day.

Which airlines fly direct between San Juan Luis Munoz Marin Intl Airport and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport.
There are 3 airlines that fly direct from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport. They are: American Airlines, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with American Airlines at £119 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between San Juan Luis Munoz Marin Intl Airport and Chicago O'Hare Intl Airport per day?

Each day, there are between 3 and 4 nonstop flights that take off from San Juan Luis Munoz Marin Intl Airport and land in Chicago O'Hare Intl Airport, with an average flight time of 5h 11m. The most common departure time is 15:00 and most flights take off in the afternoon. Each week, there are 22 flights. The most frequent day of departure is Sunday, when 18% of all weekly flights depart. The fewest flights depart on a Tuesday.

Which cabin class options are there for flights between San Juan Luis Munoz Marin Intl Airport and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from San Juan to Chicago?

Early birds can take the earliest flight from San Juan Luis Munoz Marin Intl Airport at 04:30 and will be landing in Chicago O'Hare Intl Airport at 08:40.

What’s the latest departure time from San Juan to Chicago?

If you prefer to fly at night, the latest flight from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport jets off at 16:09 and lands at 20:20.

Good to know - Cheap tickets from San Juan to Chicago

Low season

January

High season

November
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly and prices are also 19% 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, Delta, Alaska Airlines, Iberia, British Airways, and Finnair.

  • 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.

See more FAQs

Top tips for finding a cheap flight from San Juan to Chicago

  • Looking for a cheap flight from Chicago to San Juan? 25% of our users found flights on this route for £89 or less one-way and £184 or less round-trip.

Prefer to fly direct from San Juan to Chicago?

Find which airlines fly direct from Luis Munoz Marin Intl to O'Hare Intl, 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 3 airlines serving 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.
7.4
United AirlinesOverall score based on 11202 reviews
7.7Boarding
8.1Crew
6.7Food
7.1Entertainment
7.2Comfort
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

Our flight was delayed two hours. We nearly missed our connecting flight and had to rush across the airport with little kids and all their luggage. They didn’t give us enough time to walk from one gate to the other, then when we got on, we waited another half hour while the crew loaded cargo. It seems like they could have given passengers more time if they had cargo to load anyway.

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

Book cheap flights from San Juan to Chicago

One-way flight deals

directAmerican Airlines
5h 20mSJU-ORD
directAir Canada
5h 11mSJU-ORD
directAlaska Airlines
5h 20mSJU-ORD
directAir New Zealand
5h 11mSJU-ORD
directUnited Airlines
5h 11mSJU-ORD
directSpirit Airlines
5h 05mSJU-ORD

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San Juan - Chicago Flights

Departure:

San Juan (SJU)Puerto Rico

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - San Juan

Cabin classes:

£93

Browse origins:

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  • San Juan Airport

Browse destinations:

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  • Chicago O'Hare Airport