CHI - SJU

$57 Find Cheap Flights from Chicago to San Juan Airport

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 12/9. 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

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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.
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Cheap Flight Deals from Chicago to San Juan Airport (CHI-SJU)

 
These are the cheapest deals for flights from Chicago to San Juan currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to San Juan

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to San Juan.

Recent one-way flight deals from Chicago to San Juan

Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Juan found on KAYAK recently.

Recent last minute flight deals from Chicago to San Juan

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to San Juan.

Recent direct flight deals from Chicago to San Juan

The latest deals for direct flights from Chicago to San Juan so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to San Juan

Find recent round-trip train or bus tickets from Chicago to San Juan.

All round-trip flight deals to San Juan

The cheapest plane tickets to San Juan found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$117Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$128Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
9:15 pm - 8:24 amSJU-ORD
13h 09m1 stop
$133Frontier
Find Deal
Mon, Dec 9 - Wed, Dec 11
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
5:08 pm - 6:39 amSJU-MDW
15h 31m1 stop
$133Frontier
Find Deal
Mon, Dec 16 - Wed, Dec 18
1:20 pm - 12:50 amMDW-SJU
9h 30m2 stops
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$210Southwest
Find Deal
Sun, Feb 2 - Wed, Feb 5
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
$216United Airlines
Find Deal
Mon, Dec 9 - Mon, Dec 16
12:53 pm - 12:36 amORD-SJU
9h 43m1 stop
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
$247United Airlines
Find Deal
Mon, Dec 9 - Sun, Dec 15
1:20 pm - 9:40 pmMDW-SJU
6h 20m1 stop
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$275Southwest
Find Deal
Wed, Jan 15 - Thu, Jan 23
12:44 pm - 11:45 pmMDW-SJU
9h 01m1 stop
3:30 pm - 10:20 pmSJU-MDW
8h 50m1 stop
$334Delta
Find Deal
Tue, Jan 28 - Thu, Jan 30
12:44 pm - 11:46 pmMDW-SJU
9h 02m1 stop
6:15 am - 11:59 amSJU-MDW
7h 44m1 stop
$379Delta
Find Deal
Tue, Feb 18 - Tue, Feb 25
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
$57Frontier
Find Deal
Mon, Dec 9
5:28 pm - 2:19 amORD-SJU
6h 51m1 stop
$63Frontier
Find Deal
Mon, Jan 20
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
$64Spirit Airlines
Find Deal
Wed, Jan 1
9:32 pm - 12:01 pmORD-SJU
12h 29m1 stop
$81Spirit Airlines
Find Deal
Fri, Dec 6
5:50 pm - 6:12 amORD-SJU
10h 22m1 stop
$105United Airlines
Find Deal
Sat, Jan 11
7:35 am - 9:46 pmORD-SJU
12h 11m1 stop
$125United Airlines
Find Deal
Tue, Feb 18
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
$167Delta
Find Deal
Tue, Jan 14
8:20 am - 2:00 pmORD-SJU
4h 40mnonstop
$188American Airlines
Find Deal
Sun, Mar 9
1:54 pm - 12:42 amORD-SJU
8h 48m2 stops
$207American Airlines
Find Deal
Mon, Nov 25
7:30 am - 4:20 pmORD-SJU
7h 50m1 stop
$247Delta
Find Deal
Thu, Mar 13
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
2:45 am - 10:56 amSJU-ORD
10h 11m1 stop
$244Spirit Airlines
Find Deal
Thu, Nov 21 - Mon, Nov 25
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
4:00 pm - 7:26 pmSJU-ORD
5h 26mnonstop
$252Spirit Airlines
Find Deal
Thu, Nov 21 - Tue, Dec 3
2:56 pm - 2:20 amMDW-SJU
9h 24m1 stop
8:10 pm - 8:21 amSJU-MDW
14h 11m1 stop
$282Frontier
Find Deal
Sat, Nov 23 - Tue, Dec 31
8:21 pm - 10:57 amORD-SJU
12h 36m1 stop
7:30 am - 1:27 pmSJU-ORD
7h 57m1 stop
$288Frontier
Find Deal
Mon, Nov 25 - Thu, Nov 28
7:35 am - 9:26 pmORD-SJU
11h 51m1 stop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$367United Airlines
Find Deal
Sat, Nov 23 - Wed, Nov 27
7:35 am - 9:26 pmORD-SJU
11h 51m1 stop
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
$402United Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
5:00 am - 3:43 pmORD-SJU
8h 43m2 stops
3:29 pm - 12:16 amSJU-ORD
10h 47m1 stop
$414American Airlines
Find Deal
Sun, Nov 24 - Wed, Nov 27
5:00 am - 3:43 pmORD-SJU
8h 43m2 stops
5:50 am - 2:43 pmSJU-ORD
10h 53m2 stops
$425American Airlines
Find Deal
Mon, Nov 25 - Thu, Nov 28
6:00 am - 2:31 pmMDW-SJU
6h 31m1 stop
1:50 pm - 9:46 pmSJU-MDW
9h 56m1 stop
$479Delta
Find Deal
Fri, Nov 22 - Thu, Nov 28
7:10 am - 5:13 pmORD-SJU
8h 03m1 stop
3:41 pm - 11:59 pmSJU-ORD
10h 18m1 stop
$484Delta
Find Deal
Fri, Nov 22 - Mon, Dec 2
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$117Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$128Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$129Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$131Spirit Airlines
Find Deal
Mon, Jan 6 - Wed, Jan 15
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$132Spirit Airlines
Find Deal
Mon, Jan 6 - Wed, Jan 15
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$211United Airlines
Find Deal
Tue, Dec 10 - Fri, Dec 13
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$277United Airlines
Find Deal
Tue, Mar 4 - Sat, Mar 8
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:20 pm - 7:40 pmSJU-ORD
5h 20mnonstop
$346American Airlines
Find Deal
Tue, Apr 8 - Tue, Apr 15
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
$354American Airlines
Find Deal
Wed, Dec 11 - Tue, Dec 17
8:45 am - 3:20 pmMDW-SJU
4h 35mnonstop
5:00 pm - 8:15 pmSJU-MDW
5h 15mnonstop
$1,233Southwest
Find Deal
Sat, Feb 15 - Sat, Feb 22

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 $90 and was between Chicago O'Hare Intl 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 $168.

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 Fridays 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 August, where tickets cost $290 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $502 and $446 respectively.

Can I save money by flying with a layover from Chicago to San Juan Luis Munoz Marin Intl Airport?

The average price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $308 on average

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 1 day before departure. For the absolute cheapest price, our data suggests you should book 9 days before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$57
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 42% 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 $57 for a one-way ticket and $117 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, and JetBlue 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Southwest and Delta. With an average price for the route of $422 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $428 and an overall rating of 8.0.

  • 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

KAYAK’s top tips for finding a cheap flight from Chicago to San Juan Luis Munoz Marin Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $159 or less one-way and $286 or less round-trip.

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

Find which airlines fly direct from Chicago to San Juan Luis Munoz Marin Intl Airport, 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, +3 more

Air Canada, Air New Zealand, +4 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, +3 more

Air Canada, Air New Zealand, +4 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 8765 reviews
8.2Boarding
8.5Crew
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

8.0 ExcellentAndrew, Nov 2024MCO - LGA
Read more Delta reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!

My flight was completely full. Making me very stressful with people walking around all the time. I believe airlines can do better for entertain people during the flight.

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

Really nice, flight attendants were so helpful with me and my kids. Extremely grateful, keep up the good work and spirit :)

The flight was delayed, and we waited for more than an hour on the plane.

Could at least have little recline in economy seats and windows to the last row, they were super uncomfortable and lots of chit chat and disturbance from the operation of crew members and other passengers

Was told by one of the helpers at spirit in Detroit that I had to pay for my bag that could fit on the over head bin after I asked her repeatedly well what about the over head bin can’t my bag fit in there she said no I had to check it. Then sent me the long way to the tsa when my gate was the other way. I didn’t have that problem in Chicago.

Cancelled after 3 hour delay with no aside from a rebooking three days later.

Nothing. Will never ever travel on Spirit or Frontier. Both of them Garbage Airlines.

There was no water offered to passengers during a four hour flight, five hours on the plane. There is no entertainment on board. The crew interrupt everyone often to sell credit cards and reward packages. Other than that, pretty typical flight. You get what you pay for.

Someone opened my checked bag and stold75 euros Not happy

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

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.
12/9Mon
1 stopFrontier
7h 04mORD-SJU
$57
1/20Mon
1 stopFrontier
6h 51mORD-SJU
$63
1/1Wed
nonstopSpirit Airlines
4h 43mORD-SJU
$64
12/6Fri
1 stopSpirit Airlines
12h 29mORD-SJU
$81
1/11Sat
1 stopUnited Airlines
10h 22mORD-SJU
$105
2/18Tue
1 stopUnited Airlines
12h 11mORD-SJU
$125
1/14Tue
1 stopDelta
6h 20mMDW-SJU
$167
3/9Sun
nonstopAmerican Airlines
4h 40mORD-SJU
$188
11/25Mon
2 stopsAmerican Airlines
8h 48mORD-SJU
$207
3/13Thu
1 stopDelta
7h 50mORD-SJU
$247

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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.
11/21Thu
multi-stopSpirit Airlines
8h 31mORD-SJU
11/25Mon
multi-stopSpirit Airlines
10h 11mSJU-ORD
$244
11/21Thu
multi-stopSpirit Airlines
8h 31mORD-SJU
12/3Tue
nonstopSpirit Airlines
5h 26mSJU-ORD
$252
11/23Sat
multi-stopFrontier
9h 24mMDW-SJU
12/31Tue
multi-stopFrontier
14h 11mSJU-MDW
$282
11/25Mon
multi-stopFrontier
12h 36mORD-SJU
11/28Thu
multi-stopFrontier
7h 57mSJU-ORD
$288
11/23Sat
multi-stopUnited Airlines
11h 51mORD-SJU
11/27Wed
nonstopUnited Airlines
5h 19mSJU-ORD
$367
11/23Sat
multi-stopUnited Airlines
11h 51mORD-SJU
11/25Mon
multi-stopUnited Airlines
10h 39mSJU-ORD
$402
11/24Sun
multi-stopAmerican Airlines
8h 43mORD-SJU
11/27Wed
multi-stopAmerican Airlines
10h 47mSJU-ORD
$414
11/25Mon
multi-stopAmerican Airlines
8h 43mORD-SJU
11/28Thu
multi-stopAmerican Airlines
10h 53mSJU-ORD
$425
11/22Fri
multi-stopDelta
6h 31mMDW-SJU
11/28Thu
multi-stopDelta
9h 56mSJU-MDW
$479
11/22Fri
multi-stopDelta
8h 03mORD-SJU
12/2Mon
multi-stopDelta
10h 18mSJU-ORD
$484

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