SJU - CHI

$123 Find Cheap Flights from San Juan to Chicago

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 8/20. 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
1 adult, Economy, 0 bags

KAYAK searches 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
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Everything you should know

Cheapest round-trip
$240
Typical prices: $244-$417
Frontier
Tue 8/18Tue 8/25
SJU - ORD • Non-stop
Cheapest non-stop
$239
Typical prices: $270-$470
Frontier
Fri 7/3Mon 7/6
SJU - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six extra inches of legroom over standard economy.
American Main Cabin Extra includes early boarding and complimentary drinks.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $240 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Frontier and others. Average duration is 5h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 59% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 96% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $157 (round-trip)
Shortest trip • 7h 04m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 66% price drop
Most popular
Good to know
Good to know
+1
+1
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Flight Deals
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Juan to Chicago

Tue, Aug 18 - Tue, Aug 25
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$240Frontier
Thu, Aug 20 - Fri, Aug 21
Southwest Logo
8:55 pm - 8:45 am
SJU
-
MDW
12h 50m
1 stop
Southwest Logo
11:15 am - 10:10 pm
MDW
-
SJU
9h 55m
1 stop
$241Southwest
Wed, Aug 26 - Sat, Aug 29
United Airlines Logo
2:20 pm - 11:26 pm
SJU
-
ORD
10h 06m
1 stop
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
$242United Airlines
Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
5:37 pm - 12:50 pm
SJU
-
ORD
44h 13m
2 stops
Multiple Airlines Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$243Multiple Airlines
Thu, Jul 9 - Sat, Jul 11
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$244Frontier
Wed, Sep 2 - Sat, Sep 5
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
7:11 am - 12:56 am
ORD
-
SJU
16h 45m
2 stops
$245Frontier
Wed, Aug 26 - Mon, Aug 31
Delta Logo
2:59 pm - 8:55 pm
SJU
-
ORD
6h 56m
1 stop
Delta Logo
5:30 am - 4:38 pm
ORD
-
SJU
10h 08m
1 stop
$246Delta
Wed, Aug 26 - Wed, Sep 2
American Airlines Logo
7:24 pm - 7:34 am
SJU
-
ORD
13h 10m
1 stop
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
$247American Airlines
Fri, Aug 28 - Sun, Aug 30
American Airlines Logo
3:44 pm - 11:30 pm
SJU
-
ORD
8h 46m
1 stop
American Airlines Logo
6:45 am - 10:24 pm
ORD
-
SJU
14h 39m
1 stop
$250American Airlines
Wed, Aug 26 - Sat, Aug 29
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
6:11 am - 4:38 pm
MDW
-
SJU
9h 27m
1 stop
$256Delta
Booking Insights

KAYAK's insights & trends for San Juan to Chicago flights

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.

How much is a round-trip flight from San Juan Luis Munoz Marin Intl Airport to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago departing in August.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from San Juan Luis Munoz Marin Intl Airport to Chicago costs $172 on the route between San Juan Luis Munoz Marin Intl Airport (SJU) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 59% cheaper than other San Juan Luis Munoz Marin Intl Airport-Chicago routes. It is also the most popular route.

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

The average price of all round-trip 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 Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Monday is the cheapest day to fly and Friday 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 round-trip 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 May, where tickets cost $64 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $786 and $558 respectively.

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

The average round-trip 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 $398 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

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 10 weeks before departure.

Expert advice

Expert advice for your flight from San Juan to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Gabriel Leigh

Gabriel Leigh

Expert on SJU

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Good to know

Low seasonNovember
Cheapest flight$123
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 5 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago was $123 for a one-way ticket and $240 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, and Delta 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 Airbus A321neo 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between San Juan and Chicago, with SkyTeam 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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are United Airlines and American Airlines. With an average price for the route of $477 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 $466 and an overall rating of 7.1.

  • 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $201 or less one-way and $353 or less round-trip.

Prefer to fly direct from San Juan to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San Juan Luis Munoz Marin Intl to Chicago.
Find which airlines fly direct from San Juan Luis Munoz Marin Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

San Juan Luis Munoz Marin Intl to Chicago

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Chicago to San Juan Luis Munoz Marin Intl

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Reviews of the top 4 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.
7.4
United AirlinesOverall score based on 9896 reviews
7.7Boarding
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
Airline reviews

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

2.0 MediocreRuss, Jun 2026
FOD - ORD
Read more United Airlines reviews

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Awful. There was a minor problem with a fridge and they had us 2 hours in the runway before take off. The paper work alone took them half hour. There was no attemp to make up time up while in teansit and when we arrived, they had us another half hour in the plane because of traffic. I, and a bunch of people, lost their onnection flights for 5 to 10 minutes. Not even the attemp to wait given thar all delays, but the taxing, were United's fault. Then another 45 mins to get an agent and no flight alternatives for 2 days. Im am very disapointed with this "premium carrier".

IT WAS A LONG TIME SINCE THE LAST TIME I TRAVELED. I THOUGHT I WAS TO BE LOST BUT EVERYONE WAS PRETTY NICE WITH ME AND MADE MY EXPERIENCE NICE. THANKS

There was a delay that was unexpected. The seats were uncomfortable for the length of the flight.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

AA was a very good experience. The employees are wonderful

We had a very pleasant flight with very comfortable seats and nice staff.

Seats in coach aren't padded enough for a 6 hour flight

My trip was delayed for more than 3 hours without any explanation. Also I have a business meeting that I lost.

the handling of my luggage. It was Lost or stolen At my destination.

If we travel with carry on expected to being able to carry the luggage. Could be good if take in consideration the date of reservation to do that

I will NEVER fly with this clown show airline again. Idiots. All of them. Unprepared. Unfriendly. Miserable employees. NEVER. EVER. AGAIN

Easy experience even with the outbound flight being delayed. The seating and space was comfortable and the crew seemed very nice and helpful.

Flight was smooth, amenities (entertainment options and power outlets) were good, sears decent)

Disaster This is why I stick to delta You get what you pay for

Well, its a hit or miss when boarding most of the time your employees just let everyone enter immediately In one bum rush. Then out of know where tell the passengers only let A can enter then b then c etc. So make a decision and stick to it. Do it by alphabet and have famn strick compliance. Let the public know. That makes easier on passengers.

It was a pretty smooth flight, I tend to get mini anxiety attacks during flights, however, this time was pretty smooth and I was able to relax. The only thing, I was having issues to connect to the Flyfi internet. I was not able to connect at all, I turned off my phone a couple times and didnt work.

we were delayed because of some safety check that wasn't done or available

They announced at the last minute that international travelers had to checkin at counter. This created a long line and unnecessary stress.

I cannot say this enough, I NEVER BOARDED OR HAVE HAD ANY TRAVEL IN THE PAST YEAR. However your app says ive been traveling a lot lately. GET REAL HUMANS TO GIVE CUSTOMER SUPPORT.

late lack information taney changed my sit even after i had checked i. a day prior and had been at airport checked in for 5 hrs. i have medical condition that i need to sit in aisle but changes to window. only apparent at boarding and they had no explanation why they changed my boarding pass and had no other seats. very bizarre, uncaring and disrespectful. Made my trip very challenging I should sue you. will NEVEr fly JB again. Ever. Would have blasted in social media but did not want to disclose my medical disability.

Frontier line changes my flight schedule with out my authorization. They never ask me and with out my concern they cut off 4 hours of my vacation they force my to leave 4 hours early from Puerto Rico.

Good- no snacks on a 4+ hour flight is painful but more painful was the lack of WiFi.

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Flight was changed (according to Frontier, by Kayak) without my notification. And all flights were delayed by at least an hour and a half. Uncomfortable plane. Bad service. Will never fly Frontier again.

Was left with many other passengers in SJU by frontier airlines due to delay caused by frontier. Worst experience ever and worst airline ever.

It was horrible. My plane was delayed until the next day resulting in me losing a day of work. It’s absolutely unacceptable and I won’t be flying with you any more and I will strongly caution others to avoid your airline as well.

When we arrived we lasted 48 minutes to be able to get off the plane without air and the plane turned off more than half of the passengers because after they started to leave they realized that the bridge was defective

Pro: The stuff was great. Friendly, patient and caring. Our seat row was clean. The bath room was clean. Our flights were close to on time. Con: The leg room is too small. No blankets or pillows. No entertainment devices at all. I can’t remember to have a food choice. I would fly again with frontier for short distances.

Great option to American Airlines. Affordable prices when compared to AA. Prices in AA to and from Puerto Rico are like Fly Emirates to Kwait.

The flights were right on time. The issue that was the most difficult was the lack of legroom on the planes

Everything you need to know for your flight from San Juan to Chicago

Information on your arrival and departure airports