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SJU - CHI

Find cheap flights from San Juan to Chicago from $71

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 6/4. 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
Tue 6/4
Tue 6/11

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 42,830,901 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
10:18 pm - 6:54 amSJU-MDW
9h 36m1 stop
10:16 am - 11:54 pmMDW-SJU
12h 38m1 stop
$140Frontier
Find Deal
Sat, May 18 - Tue, May 21
9:34 am - 6:27 pmSJU-MDW
9h 53m1 stop
7:23 pm - 1:25 amMDW-SJU
29h 02m1 stop
$152Frontier
Find Deal
Wed, May 15 - Sun, May 19
12:46 pm - 7:00 pmSJU-ORD
7h 14m1 stop
5:05 am - 5:52 pmORD-SJU
11h 47m1 stop
$181Spirit Airlines
Find Deal
Sat, Jun 1 - Sat, Jun 8
12:32 pm - 8:55 amSJU-ORD
21h 23m1 stop
9:15 pm - 6:57 pmORD-SJU
20h 42m1 stop
$182Spirit Airlines
Find Deal
Sat, May 25 - Tue, May 28
6:10 am - 10:20 amSJU-ORD
5h 10mnonstop
9:15 pm - 1:25 amORD-SJU
27h 10m1 stop
Thu, May 23 - Tue, May 28
9:07 pm - 9:55 amSJU-ORD
13h 48m1 stop
5:30 am - 7:22 pmORD-SJU
12h 52m1 stop
Wed, May 8 - Sun, May 12
12:45 am - 8:35 amSJU-ORD
8h 50m1 stop
6:52 am - 11:20 pmORD-SJU
15h 28m1 stop
$247American Airlines
Find Deal
Wed, May 8 - Fri, Jun 7
5:55 pm - 11:59 pmSJU-ORD
7h 04m1 stop
7:30 am - 8:15 pmORD-SJU
11h 45m1 stop
$263American Airlines
Find Deal
Fri, May 10 - Mon, May 13
2:25 pm - 9:44 pmSJU-MDW
8h 19m1 stop
10:11 am - 10:03 pmMDW-SJU
10h 52m1 stop
$455Delta
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
$609Delta
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, 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 January, where tickets cost $196 on average. On the other hand, the most expensive months are March and July, where the average cost of tickets is $363 and $316 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 15 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 $71. KAYAK users also found San Juan to Chicago round-trip flights on Frontier from $140 and on Spirit Airlines from $181.

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 27 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 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

February

High season

December

Cheapest flight

$71
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San Juan to Chicago Midway 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 $71 for a one-way ticket and $140 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 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 $360 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 $434 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 $259 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 10826 reviews
7.4Food
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
Airline reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

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 !

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 CX617 from HK to BKK was delayed more than 1.5 hours.

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 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...

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

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.

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.
6/4Tue
1 stopFrontier
13h 28mSJU-MDW
$71
5/29Wed
1 stopFrontier
10h 08mSJU-MDW
$90
6/1Sat
2 stopsSpirit Airlines
14h 48mSJU-ORD
$105
6/25Tue
1 stopSpirit Airlines
14h 55mSJU-ORD
$106
5/13Mon
1 stopAmerican Airlines
9h 40mSJU-ORD
$133
5/9Thu
1 stopAmerican Airlines
7h 04mSJU-ORD
$135
7/27Sat
1 stopDelta
7h 52mSJU-ORD
$177
7/2Tue
1 stopUnited Airlines
8h 30mSJU-ORD
$236
6/7Fri
1 stopUnited Airlines
7h 55mSJU-ORD
$252
6/8Sat
1 stopDelta
9h 56mSJU-MDW
$377

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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.
5/10Fri
nonstopSpirit Airlines
5h 10mSJU-ORD
5/14Tue
multi-stopSpirit Airlines
15h 52mORD-SJU
$135
5/9Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
5/14Tue
multi-stopSpirit Airlines
20h 42mORD-SJU
$162
5/8Wed
multi-stopAmerican Airlines
8h 50mSJU-ORD
6/7Fri
multi-stopAmerican Airlines
15h 28mORD-SJU
$247
5/9Thu
multi-stopFrontier
21h 35mSJU-ORD
5/11Sat
multi-stopFrontier
16h 25mORD-SJU
$259
5/10Fri
multi-stopFrontier
21h 34mSJU-ORD
5/18Sat
multi-stopFrontier
7h 13mORD-SJU
$262
5/10Fri
multi-stopAmerican Airlines
7h 04mSJU-ORD
5/13Mon
multi-stopAmerican Airlines
11h 45mORD-SJU
$263
5/7Tue
multi-stopUnited Airlines
9h 30mSJU-ORD
5/12Sun
nonstopUnited Airlines
4h 50mORD-SJU
$272
5/10Fri
multi-stopUnited Airlines
10h 35mSJU-ORD
5/18Sat
multi-stopUnited Airlines
12h 25mORD-SJU
$348
5/8Wed
multi-stopDelta
8h 30mSJU-MDW
5/15Wed
multi-stopDelta
13h 20mMDW-SJU
$3,248
5/8Wed
multi-stopDelta
10h 12mSJU-MDW
5/15Wed
multi-stopDelta
11h 24mMDW-SJU
$3,893

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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