When is the best time to book a flight from Chicago to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $250). Flying from Chicago to Puerto Rico in March is currently the most expensive (average of $338). 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.

How recently were the Chicago to Puerto Rico flight deals updated?

The Chicago to Puerto Rico flight deals you see on this page were last updated on 5/15.

What are the most popular airlines that fly from Chicago to Puerto Rico?

When booking a flight from Chicago to Puerto Rico, you may want to consider flying on American Airlines, Alaska Airlines or JetBlue as they are the most popular for this route.

What are the most popular routes from Chicago to Puerto Rico?

The most popular flight routes from Chicago to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Aguadilla Borinquen.

What are the cheapest flights from Chicago to Puerto Rico?

On average you can expect to pay $527 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $87 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $114.

What are the most reliable airlines from Chicago to Puerto Rico?

Before booking your flight to Puerto Rico from Chicago, check out the most reliable airlines to get you to your destination on time: Alaska Airlines (93%), American Airlines (92%), United Airlines( 83%).

Can I find flights from Chicago to Puerto Rico for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Puerto Rico for under $200. The cheapest flight booked recently is on Spirit Airlines for just $114, but on average you can expect to pay $152.

Are there nonstop flights from Chicago to Puerto Rico for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $200. A good price for a nonstop flight from Chicago to Puerto Rico is less than $213.

Are there last-minute flights available from Chicago to Puerto Rico for under $200?

There are currently 20+ open flights from Chicago to Puerto Rico within the next 7 days for less than $200.

What does ORD to SJU mean?

Chicago O'Hare Intl Airport is ORD and San Juan Luis Munoz Marin Intl Airport is SJU. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Aguadilla Borinquen Airport (BQN), Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Culebra Airport (CPX), Vieques Airport (VQS).

Can I find deals for flights from Chicago to Puerto Rico that include extra baggage allowance?

The amount of baggage you can bring on your Chicago to Puerto Rico flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

Can I find deals on flights from Chicago to Puerto Rico with specific airlines?

Yes, Cheapflights allows you to browse and filter Chicago to Puerto Rico flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

Can I find deals for flights from Chicago to Puerto Rico that include hotel bookings?

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

How can I find direct flights from Chicago to Puerto Rico?

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

Can I find deals for business class flights from Chicago to Puerto Rico?

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

Can I find deals for flights from Chicago to Puerto Rico that allow pets onboard?

Many airlines flying from Chicago to Puerto Rico offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

Can I find deals on last-minute flights from Chicago to Puerto Rico?

Yes, you can often find last-minute deals on Chicago to Puerto Rico flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

Cheap Flights from Chicago, IL to Puerto Rico from $87 - Find Tickets & Airfare Deals at Cheapflights.com

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

Find a great deal and save up to 20% by booking at least 57 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Puerto Rico within the next two weeks, with the cheapest ticket starting at $258.

What is the cheapest month to fly from Chicago to Puerto Rico?

October is one of the best times of the year to fly to Puerto Rico from Chicago. Prices for October average $318 per person but you can even find prices for as low as $90. The most expensive prices can be found in the month of March. Opting for a October flight can save you 60% on your journey compared to booking in March

When is the cheapest time to fly from Chicago to Puerto Rico (CHI - PR)?

When flying from Chicago to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Spirit Airlines flights from Chicago to Puerto Rico

Take a look at some of the lowest-priced Spirit Airlines flights heading from Chicago to Puerto Rico. Deals update often to give you more flight options matching your criteria

Tue 8/205:00 amORD - SJU

1 stop13h 11mSpirit Airlines

Tue 8/2712:28 pmSJU - ORD

1 stop10h 28mSpirit Airlines

Deal found 5/15$114

Tue 8/207:27 amORD - SJU

1 stop10h 30mSpirit Airlines

Tue 8/2712:28 pmSJU - ORD

1 stop10h 28mSpirit Airlines

Deal found 5/15$127

Thu 5/309:03 amORD - SJU

1 stop8h 54mSpirit Airlines

Mon 6/39:07 pmSJU - ORD

1 stop13h 48mSpirit Airlines

Deal found 5/15$129

Wed 9/1110:33 amORD - SJU

1 stop7h 38mSpirit Airlines

Sat 9/2112:28 pmSJU - ORD

1 stop9h 04mSpirit Airlines

Deal found 5/14$131

Tue 9/1010:33 amORD - SJU

1 stop7h 38mSpirit Airlines

Tue 9/1712:28 pmSJU - ORD

1 stop10h 28mSpirit Airlines

Deal found 5/15$135

Tue 8/2010:33 amORD - SJU

1 stop7h 38mSpirit Airlines

Tue 8/274:01 pmSJU - ORD

Nonstop5h 13mSpirit Airlines

Deal found 5/15$137

Mon 9/166:32 pmORD - SJU

1 stop15h 56mSpirit Airlines

Sat 9/2112:28 pmSJU - ORD

1 stop9h 04mSpirit Airlines

Deal found 5/15$148

Tue 8/207:03 amORD - SJU

2 stops10h 54mSpirit Airlines

Tue 8/2712:28 pmSJU - ORD

1 stop10h 28mSpirit Airlines

Deal found 5/15$152

Thu 5/3010:03 amORD - SJU

1 stop7h 54mSpirit Airlines

Mon 6/39:07 pmSJU - ORD

1 stop13h 48mSpirit Airlines

Deal found 5/15$153

Cheap Frontier flights from Chicago to Puerto Rico

To aid your search, here are some of the cheapest Frontier flights we've found from Chicago to Puerto Rico. Deals frequently update to provide users with more options.

Sat 6/12:35 pmMDW - SJU

1 stop8h 24mFrontier

Wed 6/59:36 pmSJU - MDW

1 stop9h 24mFrontier

Deal found 5/15$213

Wed 5/295:01 amORD - SJU

1 stop11h 50mFrontier

Tue 6/46:08 pmSJU - ORD

1 stop8h 00mFrontier

Deal found 5/14$218

Tue 9/1010:00 amMDW - SJU

1 stop10h 47mFrontier

Tue 9/1710:47 pmSJU - MDW

1 stop13h 08mFrontier

Deal found 5/15$219

Tue 5/2810:16 amMDW - SJU

1 stop12h 38mFrontier

Fri 5/313:08 amSJU - MDW

1 stop7h 05mFrontier

Deal found 5/16$221

Sat 6/12:35 pmMDW - SJU

1 stop8h 24mFrontier

Mon 6/312:59 amSJU - MDW

1 stop9h 22mFrontier

Deal found 5/15$226

Sat 6/12:35 pmMDW - SJU

1 stop8h 24mFrontier

Wed 6/53:57 pmSJU - MDW

2 stops20h 11mFrontier

Deal found 5/15$228

Mon 6/102:35 pmMDW - SJU

1 stop12h 01mFrontier

Sun 6/169:05 amSJU - MDW

1 stop13h 41mFrontier

Deal found 5/15$234

Tue 6/118:02 pmMDW - SJU

2 stops32h 41mFrontier

Tue 6/188:41 pmSJU - MDW

1 stop11h 50mFrontier

Deal found 5/15$235

Sat 5/189:08 pmMDW - SJU

1 stop12h 39mFrontier

Fri 5/318:09 pmSJU - MDW

1 stop14h 04mFrontier

Deal found 5/14$238

Cheap Chicago to Puerto Rico flights in May & June 2024

Scroll through some of the best deals on flights from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.

Thu 5/3011:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Mon 6/39:07 pmSJU - ORD

1 stop13h 48mSpirit Airlines

Deal found 5/15$184

Fri 5/3111:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Tue 6/49:07 pmSJU - ORD

1 stop13h 54mSpirit Airlines

Deal found 5/15$185

Tue 6/118:50 pmORD - SJU

1 stop15h 12mSpirit Airlines

Mon 6/178:06 pmSJU - ORD

1 stop14h 55mSpirit Airlines

Deal found 5/15$187

Sat 6/111:05 amORD - SJU

1 stop12h 42mMultiple Airlines

Wed 6/59:06 pmSJU - ORD

1 stop13h 55mMultiple Airlines

Deal found 5/15$188

Mon 6/35:25 pmORD - SJU

1 stop24h 32mSpirit Airlines

Tue 7/239:15 pmSJU - ORD

1 stop13h 08mSpirit Airlines

Deal found 5/15$189

Sun 6/26:32 amORD - SJU

1 stop28h 11mSpirit Airlines

Wed 6/56:00 amSJU - ORD

Nonstop5h 09mSpirit Airlines

Deal found 5/15$191

Sat 6/111:05 amORD - SJU

1 stop12h 42mMultiple Airlines

Wed 6/56:00 amSJU - ORD

Nonstop5h 09mMultiple Airlines

Deal found 5/15$192

Thu 5/309:03 amORD - SJU

1 stop8h 54mSpirit Airlines

Tue 6/412:32 pmSJU - ORD

1 stop10h 24mSpirit Airlines

Deal found 5/15$193

Wed 6/128:50 pmORD - SJU

1 stop21h 15mSpirit Airlines

Mon 6/178:06 pmSJU - ORD

1 stop14h 55mSpirit Airlines

Deal found 5/15$194

Chicago to Puerto Rico 2024 flight deals

Scroll through some of the best deals on flights from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.

Tue 7/27:36 amORD - SJU

1 stop10h 29mSpirit Airlines

Tue 7/99:06 pmSJU - ORD

1 stop13h 17mSpirit Airlines

Deal found 5/15$183

Thu 5/3011:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Mon 6/39:07 pmSJU - ORD

1 stop13h 48mSpirit Airlines

Deal found 5/15$184

Fri 5/3111:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Tue 6/49:07 pmSJU - ORD

1 stop13h 54mSpirit Airlines

Deal found 5/15$185

Tue 8/207:03 amORD - SJU

2 stops10h 54mSpirit Airlines

Sat 8/2412:28 pmSJU - ORD

1 stop9h 04mSpirit Airlines

Deal found 5/15$186

Wed 8/2811:06 amORD - SJU

Nonstop4h 55mSpirit Airlines

Tue 9/106:00 amSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 5/15$187

Sat 6/111:05 amORD - SJU

1 stop12h 42mMultiple Airlines

Wed 6/59:06 pmSJU - ORD

1 stop13h 55mMultiple Airlines

Deal found 5/15$188

Mon 6/35:25 pmORD - SJU

1 stop24h 32mSpirit Airlines

Tue 7/239:15 pmSJU - ORD

1 stop13h 08mSpirit Airlines

Deal found 5/15$189

Mon 9/165:35 pmORD - SJU

1 stop16h 53mSpirit Airlines

Sat 9/216:00 amSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 5/15$190

Sun 6/26:32 amORD - SJU

1 stop28h 11mSpirit Airlines

Wed 6/56:00 amSJU - ORD

Nonstop5h 09mSpirit Airlines

Deal found 5/15$191

Non-stop flights to Puerto Rico from Chicago

If you're seeking options on non-stop flights from Chicago to Puerto Rico, check out these fares. Users seeking other options on flights from Chicago to Puerto Rico should update the search form at the top of the page.

Tue 9/1011:06 amORD - SJU

Nonstop4h 55mSpirit Airlines

Tue 9/176:00 amSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 5/15$177

Tue 8/209:23 amORD - SJU

Nonstop4h 48mSpirit Airlines

Tue 8/274:01 pmSJU - ORD

Nonstop5h 13mSpirit Airlines

Deal found 5/15$182

Wed 8/2811:06 amORD - SJU

Nonstop4h 55mSpirit Airlines

Tue 9/106:00 amSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 5/15$187

Fri 5/3111:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Tue 6/46:10 amSJU - ORD

Nonstop5h 10mSpirit Airlines

Deal found 5/14$196

Wed 9/1111:06 amORD - SJU

Nonstop4h 55mSpirit Airlines

Sat 9/216:00 amSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 5/14$201

Tue 8/209:23 amORD - SJU

Nonstop4h 48mSpirit Airlines

Tue 8/274:01 pmSJU - ORD

Nonstop5h 13mSpirit Airlines

Deal found 5/15$202

Fri 5/3111:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Wed 6/56:00 amSJU - ORD

Nonstop5h 09mSpirit Airlines

Deal found 5/14$204

Wed 8/289:23 amORD - SJU

Nonstop4h 48mSpirit Airlines

Sat 9/76:00 amSJU - ORD

Nonstop5h 14mSpirit Airlines

Deal found 5/15$213

Wed 6/510:59 amORD - SJU

Nonstop4h 49mSpirit Airlines

Wed 6/126:00 amSJU - ORD

Nonstop5h 09mSpirit Airlines

Deal found 5/15$215

Chicago to Puerto Rico flights leaving soon

Book one of these great deals on flights from Chicago to Puerto Rico. It's wise to confirm all flight details are correct before booking.

Tue 5/219:25 pmORD - SJU

1 stop14h 16mSpirit Airlines

Wed 5/299:07 pmSJU - ORD

2 stops20h 21mSpirit Airlines

Deal found 5/14$194

Tue 5/215:56 pmORD - SJU

1 stop7h 13mMultiple Airlines

Sat 5/2512:32 pmSJU - ORD

1 stop9h 00mMultiple Airlines

Deal found 5/15$197

Sat 5/256:40 pmORD - SJU

1 stop15h 52mSpirit Airlines

Mon 6/39:07 pmSJU - ORD

1 stop13h 48mSpirit Airlines

Deal found 5/15$198

Tue 5/219:25 pmORD - SJU

1 stop14h 16mSpirit Airlines

Wed 5/2912:32 pmSJU - ORD

3 stops22h 23mSpirit Airlines

Deal found 5/14$200

Tue 5/219:25 pmORD - SJU

1 stop14h 16mSpirit Airlines

Fri 5/319:00 pmSJU - ORD

3 stops22h 23mSpirit Airlines

Deal found 5/14$201

Tue 5/219:25 pmORD - SJU

1 stop14h 16mSpirit Airlines

Thu 5/3011:07 pmSJU - ORD

1 stop11h 48mSpirit Airlines

Deal found 5/14$204

Sat 5/2511:10 amORD - SJU

Nonstop4h 53mSpirit Airlines

Mon 6/39:07 pmSJU - ORD

1 stop13h 48mSpirit Airlines

Deal found 5/15$205

Tue 5/219:25 pmORD - SJU

1 stop14h 16mSpirit Airlines

Fri 5/319:00 pmSJU - ORD

1 stop13h 55mSpirit Airlines

Deal found 5/14$206

Tue 5/219:25 pmORD - SJU

1 stop14h 16mSpirit Airlines

Fri 5/319:00 pmSJU - ORD

2 stops22h 23mSpirit Airlines

Deal found 5/14$210

One-way flights to Puerto Rico from Chicago

Take a look at some of the one-way flights we've detected from Chicago to Puerto Rico. Users can also find round-trip Chicago to Puerto Rico flights by using the search form above.

Tue 6/47:00 amORD - SJU

2 stops10h 57mSpirit Airlines

Deal found 5/15$87

Thu 5/3010:03 amORD - SJU

1 stop7h 54mSpirit Airlines

Deal found 5/14$88

Wed 5/298:09 pmORD - SJU

1 stop21h 48mSpirit Airlines

Deal found 5/14$89

Tue 6/49:57 amORD - SJU

1 stop8h 00mSpirit Airlines

Deal found 5/15$90

Mon 6/35:25 pmORD - SJU

1 stop24h 32mSpirit Airlines

Deal found 5/15$91

Wed 5/297:20 amORD - SJU

2 stops18h 45mSpirit Airlines

Deal found 5/15$95

Sat 6/225:05 amORD - SJU

1 stop11h 47mSpirit Airlines

Deal found 5/15$97

Thu 5/309:03 amORD - SJU

1 stop8h 54mSpirit Airlines

Deal found 5/15$98

Tue 5/286:32 amORD - SJU

1 stop28h 11mSpirit Airlines

Deal found 5/15$99

Find flights from Chicago to Puerto Rico within your budget

Fly from

Fly to

Budget

$114 - $373

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop13h 11m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$114

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$127

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/30

1 stop8h 54m

San Juan Luis Munoz Marin Intl

Mon 6/3

1 stop13h 48m

$129

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/11

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Sat 9/21

1 stop9h 04m

$131

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Tue 9/17

1 stop10h 28m

$135

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 5/29

1 stop12h 52m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop13h 54m

$171

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 6/1

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Tue 6/4

1 stop13h 54m

$179

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/1

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Wed 6/5

1 stop9h 24m

$213

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Fri 7/12

1 stop6h 12m

San Juan Luis Munoz Marin Intl

Sat 7/27

1 stop9h 47m

$373

Flights are sorted by cheapest first

Deals found on 5/15

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Puerto Rico

Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, Frontier and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

10,673 reviews

Check prices

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta

8.0

Very good

10,673 reviews

Delta

8.0

Very good

10,673 reviews

Check prices

Reviews

1 / 10

JetBlue

7.6

Good

4,472 reviews

Delta

8.0

Very good

10,673 reviews

Check prices

Reviews

1 / 10

United Airlines

7.4

Good

10,924 reviews

Delta

8.0

Very good

10,673 reviews

Check prices

Reviews

1 / 10

American Airlines

7.3

Good

14,514 reviews

Delta

8.0

Very good

10,673 reviews

Check prices

Reviews

1 / 10

Spirit Airlines

6.4

Okay

8,672 reviews

Delta

8.0

Very good

10,673 reviews

Check prices

Reviews

1 / 10

Related info for your journey

Can I find flights from Chicago to Puerto Rico for under $200 on Cheapflights?
Yes, there are multiple flights from Chicago to Puerto Rico for under $200. The cheapest flight booked recently is on Spirit Airlines for just $114, but on average you can expect to pay $152.
Are there nonstop flights from Chicago to Puerto Rico for under $200 on Cheapflights?
Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $200. A good price for a nonstop flight from Chicago to Puerto Rico is less than $213.
Are there last-minute flights available from Chicago to Puerto Rico for under $200?
There are currently 20+ open flights from Chicago to Puerto Rico within the next 7 days for less than $200.
What are the most popular routes from Chicago to Puerto Rico?
The most popular flight routes from Chicago to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Aguadilla Borinquen.
What are the most popular airlines that fly from Chicago to Puerto Rico?
When booking a flight from Chicago to Puerto Rico, you may want to consider flying on American Airlines, Alaska Airlines or JetBlue as they are the most popular for this route.
What are the most reliable airlines from Chicago to Puerto Rico?
Before booking your flight to Puerto Rico from Chicago, check out the most reliable airlines to get you to your destination on time: Alaska Airlines (93%), American Airlines (92%), United Airlines( 83%).
What are the cheapest flights from Chicago to Puerto Rico?
On average you can expect to pay $527 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $87 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $114.
What does ORD to SJU mean?
Chicago O'Hare Intl Airport is ORD and San Juan Luis Munoz Marin Intl Airport is SJU. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Aguadilla Borinquen Airport (BQN), Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Culebra Airport (CPX), Vieques Airport (VQS).
Can I find deals for flights from Chicago to Puerto Rico that include extra baggage allowance?
The amount of baggage you can bring on your Chicago to Puerto Rico flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.
Can I find deals on flights from Chicago to Puerto Rico with specific airlines?
Yes, Cheapflights allows you to browse and filter Chicago to Puerto Rico flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.
Can I find deals for flights from Chicago to Puerto Rico that include hotel bookings?
Yes. In addition to deals on Chicago to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Puerto Rico?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Puerto Rico.
Can I find deals for business class flights from Chicago to Puerto Rico?
Yes. Cheapflights offers flight deals from Chicago to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
Can I find deals for flights from Chicago to Puerto Rico that allow pets onboard?
Many airlines flying from Chicago to Puerto Rico offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.
Can I find deals on last-minute flights from Chicago to Puerto Rico?
Yes, you can often find last-minute deals on Chicago to Puerto Rico flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.
How recently were the Chicago to Puerto Rico flight deals updated?
The Chicago to Puerto Rico flight deals you see on this page were last updated on 5/15.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Luis Munoz Marin Intl flights

O'Hare Intl to Punta Cana flights

Midway to Luis Munoz Marin Intl flights

O'Hare Intl to Montego Bay flights

Midway to Punta Cana flights

O'Hare Intl to Oranjestad flights

O'Hare Intl to Saint Thomas Island flights

Midway to Montego Bay flights

O'Hare Intl to Nassau flights

O'Hare Intl to Simpson Bay flights

O'Hare Intl to Providenciales flights

St. Louis to Punta Cana flights

Midway to Oranjestad flights

Midway to Saint Thomas Island flights

St. Louis to Luis Munoz Marin Intl flights

St. Louis to Montego Bay flights

O'Hare Intl to Santo Domingo flights

O'Hare Intl to Bridgetown flights

O'Hare Intl to Castries flights

O'Hare Intl to George Town flights

Midway to Nassau flights

Midway to Simpson Bay flights

O'Hare Intl to Christiansted flights

O'Hare Intl to Willemstad flights

St. Louis to Saint Thomas Island flights

Midway to Santo Domingo flights

Midway to Providenciales flights

St. Louis to Nassau flights

O'Hare Intl to Kingston flights

O'Hare Intl to Puerto Plata flights

O'Hare Intl to Kingstown flights

St. Louis to Oranjestad flights

St. Louis to Providenciales flights

O'Hare Intl to Basseterre flights

O'Hare Intl to Santiago de los Caballeros flights

St. Louis to Bridgetown flights

St. Louis to George Town flights

St. Louis to Willemstad flights

St. Louis to Simpson Bay flights

Midway to George Town flights

Midway to Kingston flights

O'Hare Intl to St. John's flights

Midway to Castries flights

O'Hare Intl to Aguadilla flights

O'Hare Intl to St. George's flights

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Moline to Oranjestad flights

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Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.

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Top 7 airlines flying from Chicago to Puerto Rico

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$90	Average$262	FlexibilityNo cancel fee	On-time62%	Search Frontier flights
Spirit Airlines	Cheapest$132	Average$307	FlexibilityNo cancel fee	On-time65%	Search Spirit Airlines flights
Delta	Cheapest$137	Average$554	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights
United Airlines	Cheapest$153	Average$503	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
JetBlue	Cheapest$172	Average$461	FlexibilityNo cancel fee	On-time62%	Search JetBlue flights
Alaska Airlines	Cheapest$301	Average$479	FlexibilityNo cancel fee	On-time75%	Search Alaska Airlines flights
American Airlines	Cheapest$302	Average$485	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights

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Hourly flight availability from Chicago to Puerto Rico

0%of flight departures	Early morningMidnight to 6 am
100%of flight departures	Morning6 am to noon
0%of flight departures	AfternoonNoon to 6 pm
0%of flight departures	Evening6 pm to midnight

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When you search for this flight from Chicago to Puerto Rico, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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Cheap flights from Chicago (CHI) to Puerto Rico from $87

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight 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.

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Cheap Spirit Airlines flights from Chicago to Puerto Rico

Take a look at some of the lowest-priced Spirit Airlines flights heading from Chicago to Puerto Rico. Deals update often to give you more flight options matching your criteria

Cheap Frontier flights from Chicago to Puerto Rico

To aid your search, here are some of the cheapest Frontier flights we've found from Chicago to Puerto Rico. Deals frequently update to provide users with more options.

Cheap Chicago to Puerto Rico flights in May & June 2024

Find cheap flight options from Chicago to Puerto Rico specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.

Scroll through some of the best deals on flights from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.

Chicago to Puerto Rico 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Puerto Rico in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.

Scroll through some of the best deals on flights from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.

Non-stop flights to Puerto Rico from Chicago

If you're seeking options on non-stop flights from Chicago to Puerto Rico, check out these fares. Users seeking other options on flights from Chicago to Puerto Rico should update the search form at the top of the page.

Chicago to Puerto Rico flights leaving soon

Book one of these great deals on flights from Chicago to Puerto Rico. It's wise to confirm all flight details are correct before booking.

One-way flights to Puerto Rico from Chicago

Take a look at some of the one-way flights we've detected from Chicago to Puerto Rico. Users can also find round-trip Chicago to Puerto Rico flights by using the search form above.

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Reviews of airlines servicing Puerto Rico

Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, Frontier and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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Are there nonstop flights from Chicago to Puerto Rico for under $200 on Cheapflights?

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Alternative routes for Chicago to Puerto RicoSee prices for flight routes from nearby airports that may be better suited for you.

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Top 7 airlines flying from Chicago to Puerto Rico

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Search flights from Chicago to Puerto Rico by cabin class

Find flights from Chicago to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Chicago to Puerto Rico

Find hourly flight availability from Chicago to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 16, 2024.

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User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations

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How does Cheapflights help users find flights from Chicago to Puerto Rico?

Why should you use Cheapflights to find cheap flight tickets from Chicago to Puerto Rico?

Can Cheapflights find flights from Chicago to Puerto Rico with no change fees?

Can Cheapflights notify me if prices for flights from Chicago to Puerto Rico become cheaper?

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Alternative routes for Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.