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SJU - CHI

Find cheap flights from San Juan to Chicago from $104

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Juan to Chicago departing on 5/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/3
Mon 6/10

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 travelers have searched 43,693,958 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:15 pm - 1:25 pmSJU-ORD
17h 10m1 stop
9:25 pm - 12:41 pmORD-SJU
14h 16m1 stop
$179Spirit Airlines
Find Deal
Fri, May 17 - Mon, May 20
9:07 pm - 9:55 amSJU-ORD
13h 48m1 stop
5:00 am - 9:19 pmORD-SJU
15h 19m2 stops
$180Spirit Airlines
Find Deal
Wed, May 29 - Mon, Jun 3
3:08 am - 11:43 pmSJU-ORD
21h 35m1 stop
11:10 am - 5:03 pmORD-SJU
4h 53mnonstop
Thu, May 9 - Tue, May 14
6:15 am - 11:43 pmSJU-ORD
18h 28m1 stop
9:25 pm - 12:41 pmORD-SJU
14h 16m1 stop
Fri, May 10 - Mon, May 13
3:08 am - 11:43 pmSJU-ORD
21h 35m1 stop
5:56 pm - 9:16 pmORD-SJU
26h 20m1 stop
$205Frontier
Find Deal
Tue, May 14 - Fri, May 17
4:33 pm - 7:27 pmSJU-MDW
27h 54m1 stop
2:44 pm - 9:48 amMDW-SJU
18h 04m1 stop
$215Frontier
Find Deal
Fri, May 10 - Tue, May 14
12:45 am - 8:35 amSJU-ORD
8h 50m1 stop
12:15 pm - 8:15 pmORD-SJU
7h 00m1 stop
$266American Airlines
Find Deal
Tue, May 7 - Wed, May 15
3:15 pm - 7:25 amSJU-ORD
17h 10m1 stop
5:15 am - 5:05 pmORD-SJU
10h 50m1 stop
$275American Airlines
Find Deal
Mon, May 6 - Sun, May 12
2:31 pm - 10:01 pmSJU-MDW
8h 30m1 stop
6:00 am - 2:44 pmMDW-SJU
7h 44m1 stop
$728Delta
Find Deal
Wed, May 8 - Wed, May 15
8:15 am - 5:59 pmSJU-MDW
10h 44m1 stop
10:11 am - 7:39 pmMDW-SJU
8h 28m1 stop
$759Delta
Find Deal
Tue, Jul 23 - Sat, Jul 27

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 is the cheapest San Juan Luis Munoz Marin Intl Airport to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from San Juan Luis Munoz Marin Intl Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from San Juan Luis Munoz Marin Intl Airport to Chicago cost $75 and was between San Juan Luis Munoz Marin Intl Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $141.

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 clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from San Juan to Chicago, look for departures on Thursdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Sunday is the most expensive.

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

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, 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 is September, where tickets cost $217 on average. On the other hand, the most expensive months are March and April, where the average cost of tickets is $470 and $462 respectively.

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

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, 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, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 72 days before departure.

Which airlines provide the cheapest flights from San Juan to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $104. KAYAK users also found San Juan to Chicago round-trip flights on Spirit Airlines from $179 and on Frontier from $205.

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 non-stop between San Juan Luis Munoz Marin Intl Airport and Chicago?

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.
There are 4 airlines that fly nonstop from San Juan Luis Munoz Marin Intl Airport to Chicago. They are: American Airlines, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $116 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 per day?

Each day, there are between 3 and 6 nonstop flights that take off from San Juan Luis Munoz Marin Intl Airport and land in Chicago, with an average flight time of 5h 11m. The most common departure time is 3:00 pm and most flights take off in the afternoon, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 25 flights. The most frequent day of departure is Sunday, when 24% of all weekly flights depart. The fewest flights depart on a Monday.

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

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from San Juan to Chicago take?

A direct flight to Chicago will take on average 5h 08m to travel the 2,057 miles flying distance from San Juan.

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 4:30 am and will be landing in Chicago at 8:40 am.

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 jets off at 4:25 pm and lands at 8:20 pm.

Good to know

Low season

March

High season

July

Cheapest flight

$104
Best time to beat the crowds but there is an average 43% increase in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from San Juan Airport to Chicago O'Hare Airport

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 round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips 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

  • What is the cheapest flight from San Juan Luis Munoz Marin Intl Airport to Chicago?

    In the last 3 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago was $104 for a one-way ticket and $179 for a round-trip.

  • Do I need a passport to fly between San Juan and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in San Juan and on arrival in Chicago.

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

    American Airlines, Delta, Alaska Airlines, Finnair, and Iberia offer inflight Wi-Fi service on the San Juan to Chicago flight route.

  • 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 nonstop flights from San Juan to Chicago on a daily basis.

  • Which is the best airline for flights from San Juan to Chicago, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are Delta and American Airlines. With an average price for the route of $360 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $473 and an overall rating of 7.3.

  • 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 travelers 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 round-trip 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? 25% of our users found flights on this route for $90 or less one-way and $283 or less round-trip.

Prefer to fly non-stop from San Juan to Chicago?

Find which airlines fly direct from Luis Munoz Marin Intl to Chicago, which days they fly and book direct flights.

Nonstop departures

San Juan Luis Munoz Marin Intl to Chicago

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, +4 more

Air Canada, Air New Zealand, +5 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +4 more

Air Canada, Air New Zealand, +5 more

See more direct flights

Nonstop returns

Chicago 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, +4 more

Air Canada, Air New Zealand, +5 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +4 more

Air Canada, Air New Zealand, +5 more

See more direct flights
See more direct flights

Top 5 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.
8.0
DeltaOverall score based on 10848 reviews
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

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

Seats in coach aren't padded enough for a 6 hour flight

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.

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...

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Book cheap flights from San Juan to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Juan to Chicago found on KAYAK in the last 72 hours.
5/21Tue
1 stopFrontier
10h 22mSJU-ORD
$104
5/30Thu
2 stopsSpirit Airlines
17h 27mSJU-ORD
$105
6/10Mon
1 stopSpirit Airlines
14h 55mSJU-ORD
$106
5/8Wed
1 stopFrontier
9h 44mSJU-MDW
$109
6/9Sun
1 stopAmerican Airlines
13h 35mSJU-ORD
$118
5/10Fri
1 stopAmerican Airlines
9h 40mSJU-ORD
$133
5/6Mon
nonstopUnited Airlines
5h 11mSJU-ORD
$179
5/6Mon
1 stopUnited Airlines
10h 17mSJU-ORD
$183
7/27Sat
1 stopDelta
6h 58mSJU-ORD
$198
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$467

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Last minute flights from San Juan to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from San Juan to Chicago that are departing in the next 10 days.
5/9Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
5/11Sat
multi-stopSpirit Airlines
16h 51mORD-SJU
$170
5/9Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
5/13Mon
multi-stopSpirit Airlines
14h 16mORD-SJU
$190
5/9Thu
multi-stopFrontier
21h 35mSJU-ORD
5/13Mon
multi-stopFrontier
7h 53mORD-SJU
$221
5/8Wed
multi-stopAmerican Airlines
7h 04mSJU-ORD
5/15Wed
multi-stopAmerican Airlines
11h 45mORD-SJU
$263
5/7Tue
multi-stopAmerican Airlines
8h 50mSJU-ORD
5/15Wed
multi-stopAmerican Airlines
12h 45mORD-SJU
$264
5/6Mon
multi-stopFrontier
17h 21mSJU-MDW
5/9Thu
multi-stopFrontier
11h 39mMDW-SJU
$276
5/6Mon
multi-stopUnited Airlines
7h 34mSJU-ORD
5/8Wed
multi-stopUnited Airlines
9h 53mORD-SJU
$366
5/8Wed
nonstopUnited Airlines
5h 11mSJU-ORD
5/15Wed
nonstopUnited Airlines
4h 50mORD-SJU
$367
5/8Wed
multi-stopDelta
8h 30mSJU-MDW
5/15Wed
multi-stopDelta
7h 44mMDW-SJU
$728
5/8Wed
multi-stopDelta
7h 06mSJU-MDW
5/15Wed
multi-stopDelta
13h 20mMDW-SJU
$3,300

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San Juan - Chicago Flights

Departure:

San Juan (SJU)Puerto Rico

Return flight deals:

Chicago - San Juan

Cabin classes:

$1,177
$1,033
$1,097
$141