What airlines fly to San Juan?

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to San Juan from Chicago according to our data. Spirit Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to San Juan. Keep in mind that there are 7 different airlines that fly to San Juan on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to San Juan on average per day?

7 flights are operational daily from Chicago to San Juan as of November 2025. The most popular departure time for this route is 8:00AM, with 63% of flights per day taking off at noon.

Which airline has the best punctuality record on Chicago to San Juan flights?

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 13% of their flights experiencing any sort of delay.

How often are flights from Chicago to San Juan delayed?

Historically, on average around 16% of flights between Chicago and San Juan have experienced a delay on any given week. The average delay length over the past 12 months has been 140 minutes.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

What is the most punctual flight time for Chicago to San Juan flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What is the cheapest airline that flies from Chicago to San Juan?

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to San Juan

How many flights depart from Chicago to San Juan on average per week?

As of November 2025, there are 53 flights per week flying from Chicago to San Juan. The most common day of the week flights depart is Tue, with 17% of flights taking off on this day.

When did momondo last update prices for flights from Chicago to San Juan?

Prices for flights from Chicago to San Juan refresh daily.

How many operators does momondo search for flights from Chicago to San Juan?

As of November 2025, there are 7 operators available to choose from for flights from Chicago to San Juan.

How old do you have to be to fly from Chicago to San Juan?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan.

What documentation or ID do you need to fly to San Juan?

The travel and health documents required for your trip to San Juan can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Juan. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$95 Cheap Flights from Chicago to San Juan in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and San Juan?

Prices are currently low for flights on this route. Typical prices usually range from $351 to $766. The lowest price recently found on this route was $208.

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Find the cheapest flights from Chicago to San Juan

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:52 pm - 11:25 pmORD-SJU

7h 33m1 stop

11:38 am - 9:48 pmSJU-ORD

12h 10m1 stop

$208Spirit Airlines

Find Deal

Sun, Dec 7 - Fri, Dec 12

6:57 pm - 12:44 pmORD-SJU

15h 47m1 stop

11:52 am - 8:09 amSJU-ORD

22h 17m1 stop

$209Multiple Airlines

Find Deal

Sat, Jan 24 - Sun, Feb 1

12:22 pm - 6:54 pmORD-SJU

4h 32mnonstop

1:22 pm - 4:37 pmSJU-ORD

5h 15mnonstop

$210Spirit Airlines

Find Deal

Sat, Feb 21 - Tue, Feb 24

7:45 am - 6:02 pmORD-SJU

8h 17m1 stop

5:22 pm - 11:10 pmSJU-ORD

7h 48m1 stop

$211JetBlue

Find Deal

Fri, Feb 6 - Sat, Feb 14

12:22 pm - 6:54 pmORD-SJU

4h 32mnonstop

11:52 am - 6:39 pmSJU-ORD

8h 47m1 stop

$212Spirit Airlines

Find Deal

Fri, Feb 6 - Mon, Feb 9

9:40 am - 7:26 pmORD-SJU

7h 46m1 stop

10:25 am - 7:36 pmSJU-ORD

11h 11m1 stop

$214JetBlue

Find Deal

Sat, Jan 17 - Sat, Jan 24

5:05 am - 2:57 pmORD-SJU

7h 52m1 stop

8:00 am - 10:35 amSJU-ORD

28h 35m1 stop

$215Frontier

Find Deal

Sun, Jan 4 - Thu, Jan 29

8:19 pm - 12:42 pmMDW-SJU

14h 23m1 stop

4:36 pm - 7:52 pmSJU-MDW

29h 16m1 stop

$215Frontier

Find Deal

Sun, Jan 18 - Thu, Jan 22

8:25 am - 5:05 pmMDW-SJU

6h 40m1 stop

6:10 am - 1:55 pmSJU-MDW

9h 45m2 stops

$225Southwest

Find Deal

Mon, Jan 12 - Thu, Jan 22

3:15 pm - 12:40 amMDW-SJU

7h 25m1 stop

5:40 am - 12:30 pmSJU-MDW

8h 50m2 stops

$227Southwest

Find Deal

Mon, Feb 9 - Wed, Feb 11

Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets

Spirit Airlines

Dec 7

ORD1:52 pmChicago O'Hare Intl

7h 33m

1 stop

SJU11:25 pmSan Juan Luis Munoz Marin Intl

Dec 12

SJU11:38 amSan Juan Luis Munoz Marin Intl

12h 10m

1 stop

ORD9:48 pmChicago O'Hare Intl

$208

Find similar

Spirit Airlines

Jan 10

ORD12:22 pmChicago O'Hare Intl

4h 32m

SJU6:54 pmSan Juan Luis Munoz Marin Intl

Jan 13

SJU1:22 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD4:37 pmChicago O'Hare Intl

$210

Find similar

Spirit Airlines

Feb 6

ORD12:22 pmChicago O'Hare Intl

4h 32m

SJU6:54 pmSan Juan Luis Munoz Marin Intl

Feb 9

SJU11:52 amSan Juan Luis Munoz Marin Intl

8h 47m

1 stop

ORD6:39 pmChicago O'Hare Intl

$212

Find similar

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets

Frontier

Feb 27

ORD10:48 amChicago O'Hare Intl

12h 54m

1 stop

SJU1:42 amSan Juan Luis Munoz Marin Intl

Mar 6

SJU2:55 amSan Juan Luis Munoz Marin Intl

8h 43m

1 stop

ORD9:38 amChicago O'Hare Intl

$215

Find similar

Frontier

Dec 15

ORD3:23 pmChicago O'Hare Intl

7h 26m

1 stop

SJU12:49 amSan Juan Luis Munoz Marin Intl

Dec 24

SJU3:55 amSan Juan Luis Munoz Marin Intl

8h 23m

1 stop

ORD10:18 amChicago O'Hare Intl

$216

Find similar

Frontier

Dec 5

ORD12:15 pmChicago O'Hare Intl

9h 41m

1 stop

SJU11:56 pmSan Juan Luis Munoz Marin Intl

Dec 14

SJU1:59 amSan Juan Luis Munoz Marin Intl

14h 04m

1 stop

ORD2:03 pmChicago O'Hare Intl

$217

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 12/7

1:52 pm-11:25 pm

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Fri 12/12

11:38 am-9:48 pm

1 stop12h 10m

$208

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

6:57 pm-12:44 pm

1 stop15h 47m

San Juan Luis Munoz Marin Intl

Sun 2/1

11:52 am-8:09 am

1 stop22h 17m

$209

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Tue 2/24

1:22 pm-4:37 pm

Nonstop5h 15m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/6

7:45 am-6:02 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Sat 2/14

5:22 pm-11:10 pm

1 stop7h 48m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/6

12:22 pm-6:54 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Mon 2/9

11:52 am-6:39 pm

1 stop8h 47m

$212

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/17

9:40 am-7:26 pm

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:25 am-7:36 pm

1 stop11h 11m

$214

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/4

5:05 am-2:57 pm

1 stop7h 52m

San Juan Luis Munoz Marin Intl

Thu 1/29

8:00 am-10:35 am

1 stop28h 35m

$215

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/18

8:19 pm-12:42 pm

1 stop14h 23m

San Juan Luis Munoz Marin Intl

Thu 1/22

4:36 pm-7:52 pm

1 stop29h 16m

$215

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 1/12

8:25 am-5:05 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Thu 1/22

6:10 am-1:55 pm

2 stops9h 45m

$225

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/9

3:15 pm-12:40 am

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Wed 2/11

5:40 am-12:30 pm

2 stops8h 50m

$227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to San Juan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the typical price of a round-trip flight between Chicago and San Juan?

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in April, then May is your next best option. Flight prices from Chicago to San Juan during May average around $353.

What is the cheapest day to depart on your flight to San Juan?

The cheapest day to depart from Chicago to San Juan is on a Tuesday when prices can be found for as low as $393. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $444.

What is the cheapest time of day to depart on your flight to San Juan?

The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $317. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $451 on average. Flights to San Juan from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to San Juan flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices

How far in advance should I book a flight to San Juan?

You are more likely to see cheaper flights to San Juan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $392 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago for as low as $335 on momondo.

What cabin class options are available on Chicago to San Juan flights?

There are 4 cabin classes available to choose from on Chicago to San Juan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan

Fastest flight time	4h 32m
Direct flights	Every day
Airports in San Juan	1 airport

The fastest flight from Chicago to San Juan takes 4h 32m

Direct flights go from Chicago to San Juan every day.

There is 1 airport near San Juan: San Juan Luis Munoz Marin Intl (SJU)

Search flight deals

How far is Chicago to San Juan by plane?
San Juan is 2052.1 mi away from Chicago. 4h 32m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to San Juan?
Prices for flights from Chicago to San Juan refresh daily.
How many operators does momondo search for flights from Chicago to San Juan?
As of November 2025, there are 7 operators available to choose from for flights from Chicago to San Juan.
How old do you have to be to fly from Chicago to San Juan?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San Juan.
What documentation or ID do you need to fly to San Juan?
The travel and health documents required for your trip to San Juan can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San Juan. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago to San Juan

Compare and see reviews for airlines that fly from Chicago to San Juan with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $106	Free Cancellation	Rating 5.8 3,099 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $140	Free Cancellation	Rating 6.3 8,158 reviews	Search Spirit Airlines flights
Delta	PriceFrom $190	Free Cancellation	Rating 7.9 7,998 reviews	Search Delta flights
JetBlue	PriceFrom $271	Free Cancellation	Rating 7.2 2,905 reviews	Search JetBlue flights
United Airlines	PriceFrom $277	Free Cancellation	Rating 7.4 9,046 reviews	Search United Airlines flights
American Airlines	PriceFrom $361	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
Southwest	PriceFrom $379	Free Cancellation	Rating 8.0 4,254 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Juan from Chicago.

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

Yes. All flights to San Juan from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to San Juan?

momondo provides multiple filters to help you find the best flight to San Juan from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to San Juan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your San Juan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

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Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan

San Juan Isla Grande Airport

San Juan Luis Munoz Marin Intl Airport

Cheap flights from Chicago to San Juan from $123

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Juan departing on 2/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

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Find the cheapest flights from Chicago to San Juan

Cheap round-trip flights

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Spirit Airlines flights from Chicago to San Juan

Our best Spirit Airlines deals on Chicago to San Juan flight tickets

Frontier flights from Chicago to San Juan

Our best Frontier deals on Chicago to San Juan flight tickets

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Use the filters below to find and compare flights from Chicago to San Juan that are best for you.

See travel insights to San Juan from

How to get the cheapest flight ticket from Chicago to San Juan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and San Juan?

What is the cheapest month to fly to San Juan?

If you’re not able to fly to San Juan in April, then May is your next best option. Flight prices from Chicago to San Juan during May average around $353.

What is the cheapest day to depart on your flight to San Juan?

The cheapest day to depart from Chicago to San Juan is on a Tuesday when prices can be found for as low as $393. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $444.

What is the cheapest time of day to depart on your flight to San Juan?

What is the cheapest Chicago to San Juan flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices

How far in advance should I book a flight to San Juan?

What cabin class options are available on Chicago to San Juan flights?

There are 4 cabin classes available to choose from on Chicago to San Juan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

What is the cheapest airline that flies from Chicago to San Juan?

Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to San Juan

What airlines fly to San Juan?

How often are flights from Chicago to San Juan delayed?

Historically, on average around 16% of flights between Chicago and San Juan have experienced a delay on any given week. The average delay length over the past 12 months has been 140 minutes.

What is the most punctual flight time for Chicago to San Juan flights?

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to San Juan flights?

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 13% of their flights experiencing any sort of delay.

How many flights depart from Chicago to San Juan on average per day?

7 flights are operational daily from Chicago to San Juan as of November 2025. The most popular departure time for this route is 8:00AM, with 63% of flights per day taking off at noon.

How many flights depart from Chicago to San Juan on average per week?

As of November 2025, there are 53 flights per week flying from Chicago to San Juan. The most common day of the week flights depart is Tue, with 17% of flights taking off on this day.

Cheap Chicago to San Juan flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San Juan

Fastest flight time

Direct flights

Airports in San Juan

How far is Chicago to San Juan by plane?

When did momondo last update prices for flights from Chicago to San Juan?

How many operators does momondo search for flights from Chicago to San Juan?

How old do you have to be to fly from Chicago to San Juan?

What documentation or ID do you need to fly to San Juan?

Best airlines flying from Chicago to San Juan

Compare and see reviews for airlines that fly from Chicago to San Juan with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Juan?

Can I find flights from Chicago to San Juan with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to San Juan?

I’m not ready to book a flight from Chicago to San Juan right now. Can momondo alert me if prices change?

An easier way to manage your San Juan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Puerto Rico

Fly into one of these airports located in San Juan

Airports listed have a maximum distance of 7.1 mi from San Juan