Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

SJU - CHI

Find cheap flights from San Juan to Chicago from $46

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 5/14. 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
Sun 5/26
Sun 6/2

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 44,738,066 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.

Bundle and saveSave money when you bundle your flight + hotel.

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
12:40 pm - 8:30 pmSJU-ORD
8h 50m1 stop
5:00 am - 5:45 pmORD-SJU
11h 45m1 stop
$93Spirit Airlines
Find Deal
Tue, May 7 - Sat, May 11
6:10 am - 10:20 amSJU-ORD
5h 10mnonstop
9:57 am - 6:57 pmORD-SJU
8h 00m1 stop
$101Spirit Airlines
Find Deal
Sat, May 11 - Tue, May 14
9:07 pm - 9:55 amSJU-ORD
13h 48m1 stop
1:30 pm - 1:16 amORD-SJU
10h 46m1 stop
Tue, May 14 - Thu, May 16
9:07 pm - 9:55 amSJU-ORD
13h 48m1 stop
5:56 pm - 2:00 amORD-SJU
7h 04m1 stop
Tue, May 14 - Fri, May 17
3:08 am - 11:52 amSJU-MDW
9h 44m1 stop
10:37 am - 3:23 amMDW-SJU
15h 46m1 stop
$136Frontier
Find Deal
Wed, May 8 - Mon, May 13
3:41 pm - 11:31 pmSJU-MDW
8h 50m1 stop
7:13 pm - 8:34 amMDW-SJU
12h 21m1 stop
$137Frontier
Find Deal
Sat, May 11 - Tue, May 14
12:45 am - 8:35 amSJU-ORD
8h 50m1 stop
9:55 am - 5:05 pmORD-SJU
6h 10m1 stop
$227American Airlines
Find Deal
Thu, May 9 - Tue, May 14
12:45 am - 8:35 amSJU-ORD
8h 50m1 stop
8:30 am - 8:15 pmORD-SJU
10h 45m1 stop
$254American Airlines
Find Deal
Mon, May 6 - Sat, May 11
12:54 pm - 9:44 pmSJU-MDW
9h 50m1 stop
10:11 am - 10:03 pmMDW-SJU
10h 52m1 stop
$428Delta
Find Deal
Tue, Oct 22 - Sat, Oct 26
12:54 pm - 9:44 pmSJU-MDW
9h 50m1 stop
6:00 am - 4:04 pmMDW-SJU
9h 04m1 stop
$599Delta
Find Deal
Thu, Oct 17 - Sun, Oct 20

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, Tuesday is the cheapest day to fly and Saturday 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, Spirit Airlines offered the best one-way deal for that route, at $46. KAYAK users also found San Juan to Chicago round-trip flights on Spirit Airlines from $93 and on Frontier from $136.

Which airlines fly most frequently between San Juan and Chicago?

American Airlines connects San Juan to Chicago with up to 2 flights per day. Spirit Airlines also offers 1 flight per day, while United Airlines follows with 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 $115 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 4 and 7 nonstop flights that take off from San Juan Luis Munoz Marin Intl Airport and land in Chicago, with an average flight time of 5h 13m. 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 32 flights. The most frequent day of departure is Sunday, when 22% of all weekly flights depart. The fewest flights depart on a Friday.

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 09m 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 3:50 pm and lands at 8:01 pm.

Good to know

Low season

March

High season

July

Cheapest flight

$46
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 $46 for a one-way ticket and $93 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, Alaska Airlines, Delta, Iberia, and Finnair 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 Airbus A320neo 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are Delta and United Airlines. With an average price for the route of $346 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $423 and an overall rating of 7.4.

  • 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 $289 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 10966 reviews
8.2boarding
8.6crew
7.4food
7.9comfort
8.0entertainment
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

Flight was delayed an no one make an announcement about it., they only have Coca Cola and nothing else., the food that was served was cold… very bad experience and service

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

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!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

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...

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

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

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.
5/14Tue
1 stopSpirit Airlines
13h 48mSJU-ORD
$46
5/7Tue
1 stopSpirit Airlines
8h 50mSJU-ORD
$47
5/8Wed
1 stopFrontier
9h 44mSJU-MDW
$69
5/8Wed
1 stopFrontier
9h 53mSJU-MDW
$71
5/1Wed
1 stopAmerican Airlines
7h 02mSJU-ORD
$111
5/4Sat
1 stopAmerican Airlines
18h 14mSJU-ORD
$112
7/4Thu
1 stopDelta
11h 28mSJU-ORD
$172
7/9Tue
1 stopDelta
9h 54mSJU-MDW
$202
5/31Fri
1 stopUnited Airlines
7h 55mSJU-ORD
$227
7/9Tue
nonstopUnited Airlines
5h 11mSJU-ORD
$241

Search by stops

Search by airline

Search by price

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.
4/28Sun
nonstopSpirit Airlines
5h 19mSJU-ORD
4/30Tue
nonstopSpirit Airlines
4h 43mORD-SJU
$238
4/30Tue
multi-stop
21h 35mSJU-ORD
5/4Sat
multi-stop
13h 20mORD-SJU
$240
4/30Tue
multi-stopAmerican Airlines
7h 59mSJU-ORD
5/4Sat
multi-stopAmerican Airlines
16h 57mORD-SJU
$245
4/29Mon
multi-stopFrontier
22h 51mSJU-ORD
5/3Fri
multi-stopFrontier
14h 25mORD-SJU
$246
4/30Tue
multi-stopFrontier
21h 35mSJU-ORD
5/7Tue
multi-stopFrontier
8h 54mORD-SJU
$275
4/28Sun
multi-stopUnited Airlines
7h 35mSJU-ORD
4/30Tue
multi-stopUnited Airlines
8h 48mORD-SJU
$311
4/28Sun
multi-stopUnited Airlines
7h 35mSJU-ORD
5/1Wed
multi-stopUnited Airlines
12h 08mORD-SJU
$335
4/30Tue
multi-stopAmerican Airlines
19h 29mSJU-ORD
5/3Fri
multi-stopAmerican Airlines
18h 10mORD-SJU
$336
4/26Fri
multi-stopDelta
10h 24mSJU-MDW
5/3Fri
multi-stopDelta
10h 29mMDW-SJU
$3,232
4/26Fri
multi-stopDelta
15h 09mSJU-MDW
4/28Sun
multi-stopDelta
6h 17mMDW-SJU
$3,943

Search by stops

Search by airline

Search by price

San Juan - Chicago Flights

Departure:

San Juan (SJU)Puerto Rico

Return flight deals:

Chicago - San Juan

Cabin classes:

$1,177
$968
$1,080
$141