Cheap flights from Chicago (CHI) to Puerto Rico from $92

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 7/1. 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.
CHI — SJU
Jun 11 — Jun 181

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

Find a great deal and save up to 25% 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 $319 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

What is the cheapest time of day to fly from CHI to 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 Chicago to Puerto Rico flights in June & July 2024

Find cheap flight options from Chicago to Puerto Rico specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 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.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 7/1110:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$191
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Wed 7/248:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 6/5$196
Sat 6/223:56 pmORD - SJU
1 stop26h 09mSpirit Airlines
Wed 6/266:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/5$197
Wed 7/105:37 pmORD - SJU
1 stop17h 07mSpirit Airlines
Wed 7/176:40 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/6$198
Thu 6/2710:27 amORD - SJU
1 stop8h 58mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$199
Tue 7/210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 7/96:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/6$200
Tue 7/28:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Wed 7/105:45 amSJU - ORD
2 stops16h 13mSpirit Airlines
Deal found 6/5$201
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Thu 7/1810:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$201
Thu 6/279:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$202

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 3,050,429 searches. Data last updated June 6, 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.
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Thu 7/1110:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$191
Tue 7/98:50 pmORD - SJU
1 stop14h 41mSpirit Airlines
Wed 7/248:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 6/5$196
Thu 8/12:36 pmMDW - SJU
1 stop11h 36mFrontier
Wed 8/74:01 pmSJU - MDW
2 stops30h 59mFrontier
Deal found 6/6$196
Thu 9/265:05 amORD - SJU
1 stop12h 49mSpirit Airlines
Tue 10/15:40 amSJU - ORD
2 stops16h 00mSpirit Airlines
Deal found 6/6$197
Wed 7/105:37 pmORD - SJU
1 stop17h 07mSpirit Airlines
Wed 7/176:40 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/6$198
Thu 6/2710:27 amORD - SJU
1 stop8h 58mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 6/5$199
Tue 7/210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 7/96:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 6/6$200
Tue 7/28:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Wed 7/105:45 amSJU - ORD
2 stops16h 13mSpirit Airlines
Deal found 6/5$201
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Thu 7/1810:36 amSJU - MDW
1 stop14h 41mFrontier
Deal found 6/6$201

Chicago to Puerto Rico flights leaving soon

Find last-minute flight options from Chicago to Puerto Rico for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
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.
Sat 6/159:41 pmORD - SJU
1 stop21h 44mSpirit Airlines
Mon 6/178:06 pmSJU - ORD
1 stop22h 34mSpirit Airlines
Deal found 6/5$200
Wed 6/128:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 6/4$211
Sat 6/159:41 pmORD - SJU
1 stop21h 44mSpirit Airlines
Tue 6/259:06 pmSJU - ORD
2 stops20h 01mSpirit Airlines
Deal found 6/5$212
Wed 6/125:05 amORD - SJU
2 stops35h 00mSpirit Airlines
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 6/4$215
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Sat 6/1512:41 pmSJU - ORD
1 stop9h 10mSpirit Airlines
Deal found 6/4$216
Sat 6/159:41 pmORD - SJU
1 stop20h 24mSpirit Airlines
Wed 6/1912:41 pmSJU - ORD
1 stop21h 23mSpirit Airlines
Deal found 6/5$217
Sat 6/159:41 pmORD - SJU
1 stop21h 44mSpirit Airlines
Tue 6/259:06 pmSJU - ORD
3 stops27h 44mSpirit Airlines
Deal found 6/5$219
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Sat 6/154:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 6/4$222
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Fri 6/148:06 pmSJU - ORD
1 stop21h 22mSpirit Airlines
Deal found 6/4$225

One-way flights to Puerto Rico from Chicago

Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
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.
Mon 7/15:05 amORD - SJU
1 stop11h 06mSpirit Airlines
Deal found 6/4$92
Tue 7/210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 6/6$93
Tue 8/208:30 amORD - SJU
2 stops27h 33mSpirit Airlines
Deal found 6/5$94
Wed 7/1711:48 amORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 6/6$95
Mon 7/88:00 amORD - SJU
1 stop6h 23mFrontier
Deal found 6/6$96
Tue 7/97:37 pmMDW - SJU
1 stop6h 35mFrontier
Deal found 6/6$96
Mon 8/129:59 pmORD - SJU
2 stops12h 45mSpirit Airlines
Deal found 6/5$98
Wed 7/175:37 pmORD - SJU
1 stop17h 07mSpirit Airlines
Deal found 6/6$99
Tue 7/169:45 pmMDW - SJU
2 stops16h 08mFrontier
Deal found 6/5$99

Find flights from Chicago to Puerto Rico within your budget

Customize your flight search to find flights from Chicago to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$106 - $344

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop20h 09m

San Juan Luis Munoz Marin Intl

Wed 9/11

1 stop22h 07m

$106

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Wed 9/11

Nonstop4h 59m

$114

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Wed 9/11

1 stop15h 16m

$122

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Wed 9/11

Nonstop4h 59m

$125

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop20h 09m

San Juan Luis Munoz Marin Intl

Wed 9/11

2 stops25h 20m

$127

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 9/30

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Mon 10/7

1 stop11h 21m

$224

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 7/9

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Tue 7/16

1 stop24h 26m

$227

Chicago O'Hare IntlAguadilla Borinquen

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sat 10/12

1 stop8h 24m

Aguadilla Borinquen

Sat 11/2

1 stop8h 34m

$288

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/20

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Sat 8/24

1 stop8h 27m

$344

Flights are sorted by cheapest first

Deals found on 6/5

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

Best time to book a flight from Chicago to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated June 6, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, Frontier and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
9,222 reviews

Entertainment

7.3

Overall

8.1

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

8.1
Very good
9,222 reviews
8.1
Very good
9,222 reviews

Entertainment

7.3

Overall

8.1

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

8.0
Very good
10,368 reviews
8.1
Very good
9,222 reviews

Entertainment

7.3

Overall

8.1

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

7.6
Good
4,316 reviews
8.1
Very good
9,222 reviews

Entertainment

7.3

Overall

8.1

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

7.4
Good
10,696 reviews
8.1
Very good
9,222 reviews

Entertainment

7.3

Overall

8.1

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

7.3
Good
14,227 reviews
8.1
Very good
9,222 reviews

Entertainment

7.3

Overall

8.1

Crew

8.6

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 10

Crew and airport staff were excellent. They accommodated my needs and were super professional and kind.

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.
  • 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 $106, but on average you can expect to pay $140.

  • 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 $195.

  • 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?

  • 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: Air Canada (92%), United Airlines (92%), Air New Zealand( 92%).

  • What are the cheapest flights from Chicago to Puerto Rico?

    On average you can expect to pay $808 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $108 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $122.

  • 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 6/6.

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

  • What is the cheapest month 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 $245). 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.

See more FAQs

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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.

Top 7 airlines flying from Chicago to Puerto Rico

Discover the top 7 airlines that operate flights from Chicago to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$262FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$129Average$310FlexibilityNo cancel feeOn-time65%
DeltaCheapest$135Average$555FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$152Average$490FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$172Average$445FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$315Average$486FlexibilityNo cancel feeOn-time71%

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 June 6, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM
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