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San Juan

Cheap flights from Chicago (CHI) to San Juan

CHI — SJU
Oct 31 — Nov 71
Sat 10/31
Sat 11/7
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Juan are usually found in August or January, booked 83 days in advance, depart on a Tuesday or Monday and return on a Thursday

Find flight deals from Chicago to San Juan

Popular in

December

Cheapest in

August

Average price

$423
Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Best time to book a flight from Chicago to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Chicago with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to San Juan?

To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to San Juan?

Currently, August is the cheapest month in which you can book a flight from Chicago to San Juan (average of $329). Flying from Chicago to San Juan in December is currently the most expensive (average of $532). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SJU?

It’s typically best to fly out from Chicago to San Juan in the evening. Doing so could potentially save you 33% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to San Juan?

Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing San Juan

Read through reviews of airlines operating flights from Chicago to San Juan, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,208 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
Southwest
8.0
Very good
4,208 reviews
Southwest
8.0
Very good
4,208 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
United Airlines
7.4
Good
10,270 reviews
Southwest
8.0
Very good
4,208 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
JetBlue
7.1
Good
3,043 reviews
Southwest
8.0
Very good
4,208 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
American Airlines
7.0
Good
12,099 reviews
Southwest
8.0
Very good
4,208 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
Frontier
5.6
Fair
2,565 reviews
Southwest
8.0
Very good
4,208 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Edward,Sep 2026

MCO - BWI

Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.

Related info for your journey

  • What are the cheapest airlines flying from Chicago to San Juan round-trip?

    Cheapflights users have booked flights from Chicago to San Juan round-trip from $91. Other airlines that can offer you cheap pricing are Delta, from $118, and JetBlue, from $118. Frontier is priced at 77% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago to San Juan one-way?

    $75 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $79 and $123, respectively.

  • What are the most reliable airlines from Chicago to San Juan?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to San Juan on time: Air Canada (75%), United Airlines (75%), Air New Zealand (75%).

  • What are the cheapest flights from Chicago to San Juan?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $209 on average, our data indicates $710 when flying from Chicago to San Juan.

  • Where are the most common layover locations when flying from Chicago to San Juan?

    Chicago to San Juan flights have a layover in New York most of the time.

  • What are some popular things to do or see while on a layover in New York?

    Times Square, New York City Center, and Madison Square Garden are the most popular attractions in New York if you're in need of something to do during your layover. Times Square, New York City Center, and Madison Square Garden are located about 13.6 mi, 13.6 mi, and 13.6 mi, respectively from New York John F Kennedy Intl. Those landing in New York looking to spend some time exploring during their layover can rent a car for about $63 per day.

  • Where are the least popular layover locations for Chicago to San Juan flights?

    Of the flights from Chicago to San Juan that have layovers, the fewest flights stop in Orlando.

  • Can I find deals for flights from Chicago to San Juan that include hotel bookings?

    Yes. In addition to deals on Chicago to San Juan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to San Juan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Juan.

  • Can I find deals for business class flights from Chicago to San Juan?

    Yes. Cheapflights offers flight deals from Chicago to San Juan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to San Juan?

    Currently, August is the cheapest month in which you can book a flight from Chicago to San Juan (average of $329). Flying from Chicago to San Juan in December is currently the most expensive (average of $532). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top 6 airlines flying from Chicago to San Juan

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$322FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$491FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$118Average$516FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$262Average$505FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$276Average$488FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$287Average$490FlexibilityNo cancel feeOn-time71%

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