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Find cheap flights from San Juan to Illinois 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 Illinois 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
dom 6/2
dom 6/9

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Best Illinois Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicago1 stop$179
St. Louis
St. Louis1 stop$235

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

FAQs - booking Illinois flights

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

    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 Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Illinois 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 Illinois?

    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 Illinois 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 Illinois?

    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 Illinois 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 cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from San Juan to the following destinations at these prices or less: Chicago $173 one-way - $283 round-trip
  • Morning departure is around 50% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 airlines serving from San Juan to Illinois

 
Need help choosing which airline to fly with from San Juan to Illinois? 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.
9.0
Cape AirOverall score based on 57 reviews
8.9Boarding
8.4Comfort
9.5Crew
8.8Food
9.1Entertainment
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Flew business class. Everything was excellent. No issues at all. Not very many “good” movies to choose from. But lots of mediocre ones

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

The best experience that I have had traveling with JetBlue!

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

Crew was just ok. Flight was packed. On a 3/4 hour flight I would hope they would come around more than once to see if you needed anything further. Not very attentive.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

Nothing. Jet Blue is a great choice for me And I’m going to miss flying with them Since I travel to Lima Peru very often 😞😞😞

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Easy boarding and deplaning. Short flight. Water was given but that was it.

While this is a VERY SMALL plane; take-off to landing was fine. It's the constant departure time changes that wore me out and I'll try to never use this inconsistent airway again. Four delays in one day. Done!!!!!!

This has been, by far, my worst experience with an airline company. I had a reservation for a Tuesday at 8:30 pm departure from Gainesville, FL (1.5 hours - direct flight) I received an email on Monday that my flight had been changed to Monday at night to depart from Jacksonville, FL (and it was an 11 .5 hours flight ). There was no way I would have had the time to gather my things, drive 1.5 hours to the Jacksonville airport, and make it on time to board the plane. Besides, I had a full day of work on Tuesday. The only good thing I xan say about Silver airlines is that they did give me a refund, but I had to wait about 4 hours for a call back

Thank you so much for initiating these much needle in state flights especially to Gainesville. Your service and personnel are ALL awesome.

Everything was great. Keep it going. You don’t need anything else. The flights are short and everyone is so solicitous. Thank you so much for getting these much needed flights

Book cheap flights from San Juan to Illinois

Recent round-trip flight deals

5/17sex
1 stopSpirit Airlines
17h 10mSJU-ORD
5/20seg
1 stopSpirit Airlines
14h 16mORD-SJU
$179
5/29qua
1 stopSpirit Airlines
13h 48mSJU-ORD
6/3seg
2 stopsSpirit Airlines
15h 19mORD-SJU
$180
5/9qui
1 stop
21h 35mSJU-ORD
5/14ter
nonstop
4h 53mORD-SJU
$189
5/10sex
1 stop
18h 28mSJU-ORD
5/13seg
1 stop
14h 16mORD-SJU
$200
5/14ter
1 stopFrontier
21h 35mSJU-ORD
5/17sex
1 stopFrontier
26h 20mORD-SJU
$205
5/10sex
1 stopFrontier
27h 54mSJU-MDW
5/14ter
1 stopFrontier
18h 04mMDW-SJU
$215
5/7ter
1 stopAmerican Airlines
8h 50mSJU-ORD
5/15qua
1 stopAmerican Airlines
7h 00mORD-SJU
$266
5/6seg
1 stopAmerican Airlines
17h 10mSJU-ORD
5/12dom
1 stopAmerican Airlines
10h 50mORD-SJU
$275
10/4sex
2 stopsUnited Airlines
15h 44mSJU-STL
10/6dom
1 stopUnited Airlines
8h 27mSTL-SJU
$420
8/6ter
1 stopUnited Airlines
10h 28mSJU-STL
8/11dom
1 stopUnited Airlines
8h 22mSTL-SJU
$534

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Recent one-way flight deals

5/21ter
1 stopFrontier
10h 22mSJU-ORD
$104
5/30qui
2 stopsSpirit Airlines
17h 27mSJU-ORD
$105
6/9dom
1 stopAmerican Airlines
13h 35mSJU-ORD
$118
5/10sex
1 stopAmerican Airlines
9h 40mSJU-ORD
$133
6/26qua
1 stopDelta
11h 10mSJU-STL
$162
5/6seg
nonstopUnited Airlines
5h 11mSJU-ORD
$179
6/9dom
2 stops
18h 31mSJU-ORD
$181
5/6seg
1 stopUnited Airlines
10h 17mSJU-ORD
$183
8/8qui
1 stopDelta
7h 32mSJU-STL
$192
6/26qua
3 stops
23h 49mSJU-STL
$230

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Last minute flights from San Juan to Illinois

Last minute flight, train and bus deals

5/8qua
multi-stopFrontier
22h 51mSJU-ORD
5/11sáb
multi-stopFrontier
13h 14mORD-SJU
$197
5/8qua
multi-stopFrontier
9h 44mSJU-MDW
5/11sáb
multi-stopFrontier
13h 21mMDW-SJU
$216
5/4sáb
multi-stopSpirit Airlines
8h 53mSJU-ORD
5/5dom
nonstopSpirit Airlines
4h 43mORD-SJU
$221
5/8qua
multi-stop
22h 51mSJU-ORD
5/11sáb
multi-stop
16h 51mORD-SJU
$224
5/4sáb
multi-stopSpirit Airlines
8h 53mSJU-ORD
5/6seg
multi-stopSpirit Airlines
13h 28mORD-SJU
$237
5/6seg
nonstop
5h 19mSJU-ORD
5/12dom
multi-stop
12h 52mORD-SJU
$244
5/6seg
multi-stopAmerican Airlines
17h 10mSJU-ORD
5/12dom
multi-stopAmerican Airlines
10h 50mORD-SJU
$275
5/7ter
multi-stopAmerican Airlines
8h 50mSJU-ORD
5/15qua
multi-stopAmerican Airlines
8h 35mORD-SJU
$276
5/8qua
nonstopUnited Airlines
5h 11mSJU-ORD
5/15qua
nonstopUnited Airlines
4h 50mORD-SJU
$358
5/6seg
multi-stopUnited Airlines
9h 30mSJU-ORD
5/8qua
nonstopUnited Airlines
4h 50mORD-SJU
$362

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San Juan - Illinois Flights

Departure:

San Juan (SJU)Puerto Rico

Return flight deals:

Illinois - San Juan

Cabin classes:

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