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$61 Find cheap flights from Puerto Rico 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 to Chicago departing on 7/16. 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
Wed 7/10
Wed 7/17

Search 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 for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

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

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $283. On the other hand, the most expensive day to fly is Monday, where prices are $350 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights 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 to Chicago is January, where tickets cost $196 on average for one-way flights. On the other hand, the most expensive months are March and April, where the average cost of tickets from Puerto Rico is $363 and $314 respectively. For return trips, the best month to travel is January with an average price of $196.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the morning, when flights cost $275 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $324.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From San Juan Luis Munoz Marin Intl Airport $124 one-way - $243 round-trip.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, 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, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of $107.

Which airlines fly to Chicago?

Many airlines fly to Chicago, the most common ones being Spirit Airlines, United Airlines, and American Airlines. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,922 per week, followed by American Airlines with 2,998 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 80% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from San Juan, which takes 4h 59m, Aguadilla, which takes 8h 20m, and Culebra, which takes 11h 09m.

How many direct flights to Chicago are there each day?

There are around 1,627 direct flights from within Puerto Rico to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 50% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,386 direct flights from within Puerto Rico to Chicago. The most common day for departures is Friday, with 16% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 31 medium-haul flights (3-6 hour flight duration), with the most arriving from San Juan Luis Munoz Marin Intl Airport.

How many cities have direct flights to Chicago?

From Puerto Rico, there are direct flights to Chicago from 1 city. This city is San Juan Luis Munoz Marin Intl Airport and there are 31 direct flights each week.

Good to know

Low season

February

High season

July

Cheapest flight

$61
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 48% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    The distance between Chicago Midway Airport and downtown Chicago is 9 miles, which makes it the closest of the 3 Chicago airports. Chicago O'Hare Airport is 16 miles away from the center and Chicago Greater Rockford is 79 miles away.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $199. The cheapest price found on KAYAK in the last 2 weeks cost $75 and departed from San Juan Luis Munoz Marin Intl Airport.

  • How does KAYAK find such low prices on flights 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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Puerto Rico to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights

Nonstop returns

Chicago to Puerto Rico

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights
See more direct flights

Top 5 airlines serving from Puerto Rico to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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.
8.0
DeltaOverall score based on 10295 reviews
7.9Comfort
7.4Food
8.6Crew
8.2Boarding
8.0Entertainment
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Ongoing flight was delayed. Staff at bag recheck was able to get us on an earlier flight. With only 20 minutes till take off we feared our bags would not make the new earlier flight. We were most delighted that they did and were there when we landed. Delta came through

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

The flight was fine. The itinerary change from original booking was not good. We were originally leaving at 12:50 pm. The change to 8:29pm put us getting home in the early morning hours the next day. Then having to wait over an hour on the ground for a parking place to get off the plane was exhausting.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

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

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Book cheap flights from Puerto Rico to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
6/22Sat
1 stopFrontier
7h 23mSJU-MDW
6/24Mon
1 stopFrontier
12h 57mMDW-SJU
$137
8/27Tue
nonstopSpirit Airlines
4h 59mSJU-ORD
9/10Tue
1 stopSpirit Airlines
6h 45mORD-SJU
$137
9/10Tue
nonstopSpirit Airlines
4h 59mSJU-ORD
9/17Tue
1 stopSpirit Airlines
9h 24mORD-SJU
$142
6/23Sun
1 stopFrontier
23h 26mSJU-MDW
6/24Mon
1 stopFrontier
7h 45mMDW-SJU
$143
8/27Tue
nonstopSpirit Airlines
4h 59mSJU-ORD
9/10Tue
nonstopSpirit Airlines
4h 47mORD-SJU
$148
8/27Tue
1 stopSpirit Airlines
15h 01mSJU-ORD
9/10Tue
1 stopSpirit Airlines
6h 45mORD-SJU
$150
8/21Wed
1 stopSpirit Airlines
15h 01mSJU-ORD
8/27Tue
1 stopSpirit Airlines
6h 48mORD-SJU
$155
10/25Fri
1 stopDelta
10h 44mSJU-MDW
10/28Mon
1 stopDelta
9h 04mMDW-SJU
$370
12/6Fri
1 stopDelta
9h 33mSJU-MDW
12/9Mon
1 stopDelta
7h 58mMDW-SJU
$377
7/30Tue
1 stopUnited Airlines
8h 20mBQN-ORD
8/6Tue
1 stopUnited Airlines
8h 54mORD-BQN
$793

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
7/16Tue
1 stopSpirit Airlines
13h 59mSJU-ORD
$61
7/10Wed
1 stopSpirit Airlines
13h 59mSJU-ORD
$63
6/25Tue
1 stopFrontier
10h 02mSJU-MDW
$69
6/25Tue
1 stopFrontier
11h 50mSJU-MDW
$75
12/3Tue
1 stopDelta
11h 44mSJU-MDW
$172
8/19Mon
1 stopUnited Airlines
9h 29mSJU-ORD
$183
10/4Fri
2 stopsAmerican Airlines
11h 19mSJU-ORD
$191
6/15Sat
1 stopUnited Airlines
10h 30mSJU-ORD
$246
8/7Wed
2 stopsAmerican Airlines
9h 56mSJU-ORD
$250
8/17Sat
1 stopDelta
8h 27mSJU-MDW
$252

Search by stops

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Last minute flights to Chicago

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 to Chicago that are departing in the next 10 days.
6/13Thu
multi-stopFrontier
11h 50mSJU-MDW
6/20Thu
multi-stopFrontier
11h 32mMDW-SJU
$175
6/13Thu
multi-stopFrontier
11h 50mSJU-MDW
6/20Thu
multi-stopFrontier
11h 32mMDW-SJU
$178
6/14Fri
multi-stopFrontier
12h 58mSJU-MDW
6/17Mon
multi-stopFrontier
28h 52mMDW-SJU
$205
6/13Thu
nonstopSpirit Airlines
5h 09mSJU-ORD
7/13Sat
multi-stopSpirit Airlines
15h 12mORD-SJU
$216
6/13Thu
nonstopSpirit Airlines
5h 11mSJU-ORD
6/20Thu
multi-stopSpirit Airlines
10h 01mORD-SJU
$226
6/12Wed
nonstopAmerican Airlines
5h 10mSJU-ORD
6/13Thu
multi-stopAmerican Airlines
15h 33mORD-SJU
$335
6/12Wed
multi-stopAmerican Airlines
16h 50mSJU-ORD
6/13Thu
multi-stopAmerican Airlines
8h 05mORD-SJU
$358
6/11Tue
multi-stopUnited Airlines
9h 30mSJU-ORD
6/30Sun
multi-stopUnited Airlines
11h 39mORD-SJU
$404
6/11Tue
multi-stopUnited Airlines
8h 30mSJU-ORD
6/30Sun
nonstopUnited Airlines
4h 50mORD-SJU
$444
6/11Tue
multi-stopDelta
8h 46mSJU-ORD
6/17Mon
multi-stopDelta
11h 00mORD-SJU
$3,870

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Flights to Chicago

Return flight deals:

Chicago - Puerto Rico

Cabin classes:

$1,281
$826
$1,413
$141