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CHI - SJU

Find cheap flights from Chicago to San Juan Airport from $63

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Juan departing on 6/11. 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 6/9
Sun 6/16

Search hundreds of travel sites at once for deals on flights to San Juan Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan.
In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Juan 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
10:58 am - 1:25 amORD-SJU
13h 27m1 stop
9:39 am - 8:21 amSJU-ORD
23h 42m1 stop
Wed, May 29 - Tue, Jun 4
9:57 am - 6:57 pmORD-SJU
8h 00m1 stop
12:41 pm - 9:10 pmSJU-ORD
9h 29m1 stop
$138Spirit Airlines
Find Deal
Tue, Jun 4 - Tue, Jun 11
7:00 am - 1:25 amORD-SJU
17h 25m2 stops
9:39 am - 8:21 amSJU-ORD
23h 42m1 stop
Wed, May 29 - Tue, Jun 4
6:32 am - 11:43 amORD-SJU
28h 11m1 stop
7:57 pm - 9:55 amSJU-ORD
14h 58m1 stop
$144Spirit Airlines
Find Deal
Tue, May 21 - Wed, May 29
10:33 am - 7:11 pmORD-SJU
7h 38m1 stop
12:28 pm - 8:32 pmSJU-ORD
9h 04m1 stop
$148Spirit Airlines
Find Deal
Wed, Sep 11 - Sat, Sep 14
6:32 am - 11:43 amORD-SJU
28h 11m1 stop
9:07 pm - 9:55 amSJU-ORD
13h 48m1 stop
$150Spirit Airlines
Find Deal
Tue, May 21 - Wed, May 29
11:10 am - 5:03 pmORD-SJU
4h 53mnonstop
12:41 pm - 7:49 pmSJU-ORD
8h 08m1 stop
$154Spirit Airlines
Find Deal
Tue, Jun 4 - Sat, Jun 8
5:01 am - 5:51 pmORD-SJU
11h 50m1 stop
12:59 am - 10:55 amSJU-ORD
10h 56m1 stop
$197Frontier
Find Deal
Wed, May 29 - Mon, Jun 3
7:23 pm - 8:44 amMDW-SJU
12h 21m1 stop
12:59 am - 9:21 amSJU-MDW
9h 22m1 stop
$218Frontier
Find Deal
Fri, May 31 - Mon, Jun 3
10:26 pm - 2:51 pmMDW-SJU
15h 25m2 stops
10:15 pm - 9:31 amSJU-MDW
12h 16m1 stop
$219Frontier
Find Deal
Sat, Jun 8 - Sat, Jun 15

Flights from Chicago to San Juan - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to San Juan to help you find the cheapest flights, the best time to fly and much more.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to San Juan Luis Munoz Marin Intl Airport.
Our data shows that the cheapest route for a one-way flight from Chicago to San Juan Luis Munoz Marin Intl Airport cost $58 and was between Chicago Midway Airport and San Juan Luis Munoz Marin Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $59.

What’s the cheapest day of the week to fly from Chicago to San Juan Airport?

The average price of all flights from Chicago to San Juan Luis Munoz Marin Intl Airport clicked on KAYAK for each day over the last 12 months.
When flying from Chicago to San Juan Airport, you should consider leaving on a Tuesday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to San Juan Luis Munoz Marin Intl Airport, 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 Chicago to San Juan Luis Munoz Marin Intl Airport is October, where tickets cost $238 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $511 and $410 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to San Juan Luis Munoz Marin Intl Airport, 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 Chicago to San Juan Luis Munoz Marin Intl Airport, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 56 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago to San Juan Airport found by KAYAK users in the last 72 hours was for $138 on Spirit Airlines, followed by Frontier ($197). One-way flight deals have also been found from as low as $63 on Spirit Airlines and from $105 on Frontier.

Which airlines fly most frequently between Chicago and San Juan Airport?

American Airlines connects Chicago to San Juan Airport with up to 2 flights per day. Spirit Airlines also offers 2 flights per day, while United Airlines follows with 1 flight per day.

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

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to San Juan Luis Munoz Marin Intl Airport.
There are 4 airlines that fly nonstop from Chicago to San Juan Luis Munoz Marin Intl Airport. 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 $133 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 Chicago and San Juan Luis Munoz Marin Intl Airport per day?

Each day, there are between 5 and 8 nonstop flights that take off from Chicago and land in San Juan Luis Munoz Marin Intl Airport, with an average flight time of 4h 47m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 40 flights. The most frequent day of departure is Saturday, when 20% of all weekly flights depart. The fewest flights depart on a Friday.

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

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 Chicago to San Juan Airport take?

The duration of a nonstop flight to San Juan Airport from Chicago is typically 4h 40m. The journey crosses a distance of 2,057 miles.

What’s the earliest departure time from Chicago to San Juan Airport?

Early birds can take the earliest flight from Chicago at 8:05 am and will be landing in San Juan Luis Munoz Marin Intl Airport at 1:55 pm.

What’s the latest departure time from Chicago to San Juan Airport?

If you prefer to fly at night, the latest flight from Chicago to San Juan Luis Munoz Marin Intl Airport jets off at 6:07 pm and lands at 11:54 pm.

Good to know

Low season

September

High season

March

Cheapest flight

$63
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 60% increase in price.
Flight from Chicago O'Hare Airport to San Juan

When to book flights from Chicago to San Juan

Are your dates flexible? Find out the best times to travel from Chicago to San Juan 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 Chicago to San Juan Airport flights

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

    In the last 3 days, the lowest price for a flight from Chicago to San Juan Luis Munoz Marin Intl Airport was $63 for a one-way ticket and $128 for a round-trip.

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

    Yes, you’ll need a passport to travel to San Juan Airport from Chicago.

  • Which airports will I be using when flying from Chicago to San Juan Airport?

    Chicago is served by 2 major airports and there is only 1 main airport in San Juan Airport. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at San Juan Luis Munoz Marin Intl.

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

    American Airlines, Breeze Airways, JetBlue, and Delta offer inflight Wi-Fi service on the Chicago to San Juan Airport flight route.

  • Which aircraft models fly most regularly from Chicago to San Juan Airport?

    The Airbus A320neo is the aircraft model that flies most regularly on the Chicago to San Juan Airport flight route.

  • Which airline alliances offer flights from Chicago to San Juan Airport?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and San Juan Airport, with Star Alliance being the most commonly used for this route.

  • On which days can I fly direct from Chicago to San Juan Airport?

    There are nonstop flights from Chicago to San Juan Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are United Airlines and American Airlines. With an average price for the route of $472 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $483 and an overall rating of 7.3.

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

    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 Chicago to San Juan Airport.

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

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

    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 Airport with an airline and back to Chicago with another airline.

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

    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 Airport from Chicago 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 Chicago to San Juan

  • Looking for a cheap flight? 25% of our users found flights on this route for $63 or less one-way and $144 or less round-trip.

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

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top 5 airlines serving from Chicago to San Juan

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Juan. 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 Chicago 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.
8.0
DeltaOverall score based on 10768 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.6Crew
8.2Boarding
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

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!

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.

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

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.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

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.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Didn’t happen. They stranded us in Orlando and had to book a flight on frontier to get to our destination.

Flight was delayed 2+ hours missed a concert because of it…

Flight left very close to original projected time. Paid for checked bag weight overage (my fault). Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

Flight left very close to original projected time. Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

I particularly did not have no problem with my backpack, but a few people in front of me did. The chairs were really uncomfortable. Unless is a super short flight for over a weekend I wouldn't take this airline.

Do I need to call them or will you handle my complaint ? I paid for one carry-on bag. my email said up to 50 pounds when I got to the counter they charged me $79 more for my 48 pound bag!!! they said nope only 40 pounds. My email says 50 pounds. !!! I’m out another $79!!!

Flight attendant very friendly. Seats not adjustable like before. I was in the middle seat and two big guys next to me isn’t to pleasant. No used to have delays in the past and now is too often.

Seats could use more padding. Kind of hard on the tush.

Amazed that Spirit can even get planes in the air, would never use again.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

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.

Book cheap flights from Chicago to San Juan

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Juan found on KAYAK in the last 72 hours.
6/11Tue
1 stopSpirit Airlines
10h 29mORD-SJU
$63
9/18Wed
1 stopSpirit Airlines
13h 11mORD-SJU
$64
6/4Tue
nonstopSpirit Airlines
4h 53mORD-SJU
$69
6/5Wed
1 stop
29h 18mORD-SJU
$72
5/22Wed
1 stopFrontier
12h 21mMDW-SJU
$105
5/22Wed
1 stop
10h 29mORD-SJU
$106
6/17Mon
1 stopFrontier
6h 21mORD-SJU
$108
7/7Sun
1 stopAmerican Airlines
12h 12mORD-SJU
$150
5/25Sat
2 stopsAmerican Airlines
20h 13mORD-SJU
$163
5/25Sat
nonstopUnited Airlines
4h 47mORD-SJU
$189

Search by stops

Search by airline

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Last minute flights from Chicago to San Juan

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 Chicago to San Juan that are departing in the next 10 days.
5/13Mon
nonstopSpirit Airlines
4h 53mORD-SJU
5/20Mon
multi-stopSpirit Airlines
13h 48mSJU-ORD
$192
5/15Wed
nonstop
4h 53mORD-SJU
5/18Sat
multi-stop
23h 09mSJU-ORD
$205
5/14Tue
multi-stop
14h 16mORD-SJU
5/21Tue
multi-stop
23h 08mSJU-ORD
$216
5/14Tue
nonstopSpirit Airlines
4h 53mORD-SJU
5/16Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
$217
5/14Tue
multi-stopFrontier
12h 21mMDW-SJU
5/22Wed
multi-stopFrontier
16h 05mSJU-MDW
$244
5/12Sun
nonstopAmerican Airlines
4h 40mORD-SJU
5/14Tue
multi-stopAmerican Airlines
7h 04mSJU-ORD
$260
5/12Sun
nonstopAmerican Airlines
4h 40mORD-SJU
5/13Mon
multi-stopAmerican Airlines
8h 50mSJU-ORD
$262
5/13Mon
multi-stopFrontier
25h 13mORD-SJU
5/19Sun
multi-stopFrontier
22h 33mSJU-ORD
$270
5/12Sun
multi-stopUnited Airlines
8h 42mORD-SJU
5/15Wed
multi-stopUnited Airlines
7h 35mSJU-ORD
$286
5/14Tue
nonstopUnited Airlines
4h 50mORD-SJU
5/14Tue
multi-stopUnited Airlines
7h 34mSJU-ORD
$420

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Flights to San Juan Airport

Destination:

San Juan Airport (SJU)Puerto Rico

Return flight deals:

San Juan Airport - Chicago

Cabin classes:

$886
$1,021
$1,230
$59