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CHI - SJU

$49 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 6/4. 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
Sat 6/22
Sat 6/29

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 43,800,826 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to San Juan (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
7:27 am - 6:57 pmORD-SJU
10h 30m1 stop
12:28 pm - 8:25 amSJU-ORD
20h 57m1 stop
$128Spirit Airlines
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Tue, Aug 20 - Tue, Aug 27
7:27 am - 6:57 pmORD-SJU
10h 30m1 stop
6:00 am - 10:14 amSJU-ORD
5h 14mnonstop
$131Spirit Airlines
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Tue, Aug 20 - Tue, Aug 27
5:56 pm - 2:03 amORD-SJU
7h 07m1 stop
7:16 pm - 9:33 amSJU-ORD
15h 17m1 stop
Fri, Aug 16 - Mon, Aug 26
5:56 pm - 2:03 amORD-SJU
7h 07m1 stop
6:00 am - 10:14 amSJU-ORD
5h 14mnonstop
Thu, Aug 29 - Wed, Sep 4
9:05 am - 7:45 pmORD-SJU
9h 40m1 stop
12:59 am - 8:58 amSJU-ORD
8h 59m1 stop
$256JetBlue
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Fri, Oct 25 - Fri, Nov 1
10:59 am - 12:20 amMDW-SJU
12h 21m1 stop
10:47 pm - 11:33 amSJU-MDW
13h 46m1 stop
$270Frontier
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Tue, Aug 20 - Tue, Aug 27
2:35 pm - 11:59 pmMDW-SJU
8h 24m1 stop
9:36 pm - 6:00 amSJU-MDW
9h 24m1 stop
$271Frontier
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Sat, Jun 1 - Wed, Jun 5
8:30 am - 8:05 pmORD-SJU
10h 35m1 stop
10:35 pm - 7:54 amSJU-ORD
10h 19m1 stop
$293JetBlue
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Thu, Jun 20 - Sun, Jun 23
10:11 am - 10:09 pmMDW-SJU
10h 58m1 stop
8:15 am - 5:14 pmSJU-MDW
9h 59m1 stop
$373Delta
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Sat, Aug 10 - Sat, Aug 17
12:45 pm - 8:35 pmMDW-SJU
6h 50m1 stop
6:10 am - 2:55 pmSJU-MDW
9h 45m1 stop
$439Delta
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Tue, Jun 25 - Sat, Jul 6
9:15 pm - 1:02 pmORD-SJU
14h 47m1 stop
$49Spirit Airlines
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Tue, Jun 4
5:00 am - 7:11 pmORD-SJU
13h 11m1 stop
$63Spirit Airlines
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Wed, Aug 21
7:27 am - 6:57 pmORD-SJU
10h 30m1 stop
$64Spirit Airlines
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Tue, Aug 20
7:23 pm - 5:58 pmMDW-SJU
21h 35m1 stop
$88Frontier
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Mon, Jun 3
5:35 am - 5:58 pmORD-SJU
11h 23m2 stops
$97Frontier
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Tue, Jun 4
5:07 am - 11:20 pmORD-SJU
17h 13m1 stop
$138American Airlines
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Sun, Jun 16
5:00 am - 10:35 pmORD-SJU
16h 35m2 stops
$144American Airlines
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Tue, Jul 9
8:52 am - 2:42 pmORD-SJU
4h 50mnonstop
$341United Airlines
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Tue, Jun 4
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
$354United Airlines
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Thu, Nov 14
12:42 pm - 9:56 pmMDW-SJU
8h 14m1 stop
$574Delta
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Tue, May 28
1:30 pm - 1:58 amORD-SJU
11h 28m1 stop
7:57 pm - 10:01 amSJU-ORD
15h 04m1 stop
Tue, May 28 - Tue, Jun 4
5:41 pm - 11:32 amORD-SJU
16h 51m1 stop
7:57 pm - 4:07 pmSJU-ORD
21h 10m2 stops
$203Spirit Airlines
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Tue, May 28 - Tue, Jun 4
6:45 pm - 12:40 pmORD-SJU
16h 55m1 stop
3:15 pm - 10:33 pmSJU-ORD
8h 18m1 stop
$260American Airlines
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Sat, May 25 - Sun, May 26
3:35 pm - 11:57 pmORD-SJU
7h 22m1 stop
3:50 pm - 8:01 pmSJU-ORD
5h 11mnonstop
$262United Airlines
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Sat, May 25 - Wed, May 29
6:45 pm - 12:40 pmORD-SJU
16h 55m1 stop
3:15 pm - 10:33 pmSJU-ORD
8h 18m1 stop
$266American Airlines
Find Deal
Sat, May 25 - Wed, May 29
10:52 am - 11:41 pmMDW-SJU
11h 49m1 stop
7:03 pm - 7:31 amSJU-MDW
13h 28m1 stop
$288Frontier
Find Deal
Tue, May 28 - Tue, Jun 4
10:52 am - 11:41 pmMDW-SJU
11h 49m1 stop
9:36 pm - 6:00 amSJU-MDW
9h 24m1 stop
$290Frontier
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Tue, May 28 - Wed, Jun 5
8:52 am - 2:42 pmORD-SJU
4h 50mnonstop
3:50 pm - 8:01 pmSJU-ORD
5h 11mnonstop
$308United Airlines
Find Deal
Sat, May 25 - Wed, May 29
6:00 am - 4:23 pmMDW-SJU
9h 23m1 stop
12:49 pm - 10:01 pmSJU-MDW
10h 12m1 stop
$1,026Delta
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Tue, May 28 - Tue, Jun 4
6:00 am - 1:20 pmMDW-SJU
6h 20m1 stop
6:10 am - 2:55 pmSJU-MDW
9h 45m1 stop
$1,981Delta
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Mon, May 27 - Mon, Jun 10
10:26 pm - 4:11 amORD-SJU
4h 45mnonstop
6:00 am - 10:14 amSJU-ORD
5h 14mnonstop
$195Spirit Airlines
Find Deal
Sat, Aug 10 - Tue, Aug 20
9:11 am - 2:59 pmORD-SJU
4h 48mnonstop
6:00 am - 10:09 amSJU-ORD
5h 09mnonstop
$196Spirit Airlines
Find Deal
Tue, Jun 11 - Mon, Jun 17
9:11 am - 2:59 pmORD-SJU
4h 48mnonstop
6:00 am - 10:09 amSJU-ORD
5h 09mnonstop
$197Spirit Airlines
Find Deal
Tue, Jun 11 - Sun, Jun 16
11:06 am - 5:01 pmORD-SJU
4h 55mnonstop
6:00 am - 10:14 amSJU-ORD
5h 14mnonstop
$202Spirit Airlines
Find Deal
Tue, Aug 20 - Mon, Aug 26
8:52 am - 2:42 pmORD-SJU
4h 50mnonstop
3:50 pm - 8:01 pmSJU-ORD
5h 11mnonstop
$430United Airlines
Find Deal
Sun, May 26 - Tue, May 28
8:23 am - 2:03 pmORD-SJU
4h 40mnonstop
3:00 pm - 7:15 pmSJU-ORD
5h 15mnonstop
$455American Airlines
Find Deal
Sun, May 26 - Tue, May 28
8:52 am - 2:42 pmORD-SJU
4h 50mnonstop
3:50 pm - 8:01 pmSJU-ORD
5h 11mnonstop
$471United Airlines
Find Deal
Sun, May 26 - Tue, May 28
8:05 am - 1:46 pmORD-SJU
4h 41mnonstop
2:45 pm - 6:54 pmSJU-ORD
5h 09mnonstop
$493American Airlines
Find Deal
Tue, Jul 9 - Tue, Jul 16
8:52 am - 2:42 pmORD-SJU
4h 50mnonstop
3:50 pm - 8:01 pmSJU-ORD
5h 11mnonstop
$495United Airlines
Find Deal
Tue, Jul 9 - Tue, Jul 16
8:25 am - 2:10 pmORD-SJU
4h 45mnonstop
2:45 pm - 6:54 pmSJU-ORD
5h 09mnonstop
$540American Airlines
Find Deal
Wed, Jul 3 - Sun, Jul 7

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 $242 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $511 and $411 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 $128 on Spirit Airlines, followed by JetBlue ($256). One-way flight deals have also been found from as low as $49 on Spirit Airlines and from $88 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 $132 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 46m. 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 Tuesday.

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

$49
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 $49 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, Delta or JetBlue?

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Delta and JetBlue. With an average price for the route of $412 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $431 and an overall rating of 7.6.

  • 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 10561 reviews
8.6Crew
8.0Entertainment
7.9Comfort
8.2Boarding
7.4Food
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

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

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.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

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.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

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.

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.
6/4Tue
1 stopSpirit Airlines
14h 47mORD-SJU
$49
8/21Wed
1 stopSpirit Airlines
13h 11mORD-SJU
$63
8/20Tue
1 stopSpirit Airlines
10h 30mORD-SJU
$64
6/3Mon
1 stopFrontier
21h 35mMDW-SJU
$88
6/4Tue
2 stopsFrontier
11h 23mORD-SJU
$97
6/16Sun
1 stopAmerican Airlines
17h 13mORD-SJU
$138
7/9Tue
2 stopsAmerican Airlines
16h 35mORD-SJU
$144
6/4Tue
nonstopUnited Airlines
4h 50mORD-SJU
$341
11/14Thu
nonstopUnited Airlines
4h 35mORD-SJU
$354
5/28Tue
1 stopDelta
8h 14mMDW-SJU
$574

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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.
5/28Tue
multi-stop
11h 28mORD-SJU
6/4Tue
multi-stop
15h 04mSJU-ORD
$201
5/28Tue
multi-stopSpirit Airlines
16h 51mORD-SJU
6/4Tue
multi-stopSpirit Airlines
21h 10mSJU-ORD
$203
5/25Sat
multi-stopAmerican Airlines
16h 55mORD-SJU
5/26Sun
multi-stopAmerican Airlines
8h 18mSJU-ORD
$260
5/25Sat
multi-stopUnited Airlines
7h 22mORD-SJU
5/29Wed
nonstopUnited Airlines
5h 11mSJU-ORD
$262
5/25Sat
multi-stopAmerican Airlines
16h 55mORD-SJU
5/29Wed
multi-stopAmerican Airlines
8h 18mSJU-ORD
$266
5/28Tue
multi-stopFrontier
11h 49mMDW-SJU
6/4Tue
multi-stopFrontier
13h 28mSJU-MDW
$288
5/28Tue
multi-stopFrontier
11h 49mMDW-SJU
6/5Wed
multi-stopFrontier
9h 24mSJU-MDW
$290
5/25Sat
nonstopUnited Airlines
4h 50mORD-SJU
5/29Wed
nonstopUnited Airlines
5h 11mSJU-ORD
$308
5/28Tue
multi-stopDelta
9h 23mMDW-SJU
6/4Tue
multi-stopDelta
10h 12mSJU-MDW
$1,026
5/27Mon
multi-stopDelta
6h 20mMDW-SJU
6/10Mon
multi-stopDelta
9h 45mSJU-MDW
$1,981

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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:

$777
$1,063
$906
$59