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Find cheap flights from Illinois to San Juan from $58

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to San Juan departing on 5/7. 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
Thu 5/16
Thu 5/23

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Good to know

Low season

September

High season

December

Cheapest flight

$58
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 40% increase in price.
Flight from Chicago O'Hare Airport to San Juan

FAQs for booking Illinois to San Juan flights

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

    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 Illinois to San Juan.

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

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

    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 San Juan with an airline and back to Illinois with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to San Juan?

    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 San Juan from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

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

Nonstop departures

Illinois to San Juan Luis Munoz Marin Intl

Monday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Tuesday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Wednesday

Aer Lingus, Aeromexico, Air Canada, +37 more

Aer Lingus, Aeromexico, +38 more

Thursday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Friday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Saturday

Aer Lingus, Aeromexico, Air Canada, +38 more

Aer Lingus, Aeromexico, +39 more

Sunday

Aer Lingus, Aeromexico, Air Canada, +37 more

Aer Lingus, Aeromexico, +38 more

See more direct flights

Nonstop returns

San Juan Luis Munoz Marin Intl to Illinois

Monday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Tuesday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Wednesday

Aer Lingus, Aeromexico, Air Canada, +37 more

Aer Lingus, Aeromexico, +38 more

Thursday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Friday

Aer Lingus, Aeromexico, Air Canada, +36 more

Aer Lingus, Aeromexico, +37 more

Saturday

Aer Lingus, Aeromexico, Air Canada, +38 more

Aer Lingus, Aeromexico, +39 more

Sunday

Aer Lingus, Aeromexico, Air Canada, +37 more

Aer Lingus, Aeromexico, +38 more

See more direct flights
See more direct flights

Top 5 airlines serving from Illinois to San Juan

 
Need help choosing which airline to fly with from Illinois to San Juan? 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.
9.1
Cape AirOverall score based on 58 reviews
9.5crew
8.8food
8.9boarding
8.4comfort
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"

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Pros: "The crew was very interested on help and attentive with the passengers. But the seat wasn't comfortable. The design of the cushion is not the best to be seating"
Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"
Pros: "That there was seltzer"
Cons: "The management of preparing the flight and plane so that it was ready for the trip!!"
Pros: "Copa was convenient and easy. Very easy boarding process and I appreciated the day flight."
Cons: "This is a business class that is equivalent to a US carrier domestic first class. Good seats, not lay flat but wide on my 737-800. The food and service emulated say American Airlines Domestic 1C as well. Everything was just good enough, and much cheaper that international business on the majors."

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

It was good, the staff was friendly and it was a typical flight to Europe.

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!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

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

Flight was delayed a bit since booking but otherwise everything was very good.

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.

Book cheap flights from Illinois to San Juan

Recent round-trip flight deals

4/27Sat
1 stop
13h 31mSTL-SJU
5/4Sat
1 stop
9h 23mSJU-STL
$156
5/4Sat
1 stop
9h 14mSTL-SJU
5/11Sat
1 stop
7h 28mSJU-STL
$163
4/27Sat
1 stopSpirit Airlines
13h 05mSTL-SJU
5/3Fri
1 stopSpirit Airlines
9h 00mSJU-STL
$170
5/4Sat
1 stopFrontier
9h 14mSTL-SJU
5/10Fri
1 stopFrontier
13h 28mSJU-STL
$177
5/4Sat
1 stopFrontier
9h 14mSTL-SJU
5/11Sat
1 stopFrontier
12h 02mSJU-STL
$178
5/4Sat
1 stopSpirit Airlines
16h 04mORD-SJU
5/11Sat
nonstopSpirit Airlines
5h 10mSJU-ORD
$187
4/26Fri
1 stopAmerican Airlines
17h 52mORD-SJU
5/1Wed
1 stopAmerican Airlines
9h 09mSJU-ORD
$224
5/7Tue
2 stopsAmerican Airlines
10h 10mSTL-SJU
5/14Tue
1 stopAmerican Airlines
16h 58mSJU-STL
$343
9/28Sat
1 stopUnited Airlines
6h 50mPIA-SJU
10/1Tue
2 stopsUnited Airlines
10h 15mSJU-PIA
$584
5/7Tue
2 stopsUnited Airlines
19h 38mMLI-SJU
5/10Fri
2 stopsUnited Airlines
10h 18mSJU-MLI
$593

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Recent one-way flight deals

5/7Tue
1 stopSpirit Airlines
10h 35mORD-SJU
$58
5/11Sat
1 stopSpirit Airlines
16h 51mORD-SJU
$60
4/28Sun
nonstopSpirit Airlines
4h 43mORD-SJU
$67
5/18Sat
1 stopFrontier
13h 27mORD-SJU
$69
4/24Wed
1 stopFrontier
9h 27mORD-SJU
$70
4/22Mon
1 stopAmerican Airlines
7h 16mORD-SJU
$111
4/26Fri
1 stopAmerican Airlines
15h 17mORD-SJU
$112
7/31Wed
1 stopJetBlue
8h 05mORD-SJU
$165
8/19Mon
3 stopsUnited Airlines
18h 30mSTL-SJU
$348
9/27Fri
3 stopsUnited Airlines
19h 11mSTL-SJU
$381

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Last minute flights from Illinois to San Juan

Last minute flight, train and bus deals

4/17Wed
multi-stop
29h 07mMDW-SJU
4/24Wed
multi-stop
9h 53mSJU-MDW
$160
4/21Sun
nonstopSpirit Airlines
4h 43mORD-SJU
4/30Tue
multi-stopSpirit Airlines
20h 48mSJU-ORD
$197
4/18Thu
multi-stopFrontier
30h 18mMDW-SJU
4/24Wed
multi-stopFrontier
9h 53mSJU-MDW
$220
4/19Fri
multi-stopFrontier
25h 23mORD-SJU
4/21Sun
multi-stopFrontier
21h 35mSJU-ORD
$241
4/18Thu
multi-stopAmerican Airlines
6h 16mORD-SJU
4/25Thu
multi-stopAmerican Airlines
7h 59mSJU-ORD
$244
4/19Fri
multi-stopAmerican Airlines
8h 00mORD-SJU
4/22Mon
multi-stopAmerican Airlines
16h 39mSJU-ORD
$275
4/19Fri
nonstopUnited Airlines
4h 47mORD-SJU
4/21Sun
nonstopUnited Airlines
5h 11mSJU-ORD
$316
4/19Fri
nonstopUnited Airlines
4h 47mORD-SJU
4/22Mon
multi-stopUnited Airlines
9h 31mSJU-ORD
$359
4/20Sat
multi-stopDelta
9h 59mMDW-SJU
4/23Tue
multi-stopDelta
8h 44mSJU-MDW
$549
4/17Wed
multi-stopDelta
8h 14mMDW-SJU
4/23Tue
multi-stopDelta
8h 44mSJU-MDW
$734

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Flights to San Juan

Destination:

San Juan (SJU)Puerto Rico

Return flight deals:

San Juan - Illinois

Cabin classes:

$876
$1,008
$1,083
$59