Cheap flights from Chicago (CHI) to Puerto Rico from $69

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 4/25. 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
Apr 16 — Apr 231

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

Find a great deal and save up to 17% 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 $270.

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

September is one of the best times of the year to fly to Puerto Rico from Chicago. Prices for September average $370 per person but you can even find prices for as low as $111. The most expensive prices can be found in the month of March. Opting for a September flight can save you 50% 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

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Puerto Rico. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
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 4/307:27 amORD - SJU
1 stop10h 35mSpirit Airlines
Wed 5/89:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 4/10$120
Tue 5/77:27 amORD - SJU
1 stop10h 35mSpirit Airlines
Wed 5/151:32 pmSJU - ORD
1 stop8h 03mSpirit Airlines
Deal found 4/10$121
Tue 5/77:27 amORD - SJU
1 stop10h 35mSpirit Airlines
Tue 5/219:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 4/10$124
Tue 5/77:27 amORD - SJU
1 stop10h 35mSpirit Airlines
Tue 5/147:57 pmSJU - ORD
1 stop28h 32mSpirit Airlines
Deal found 4/10$126
Tue 5/77:27 amORD - SJU
1 stop10h 35mSpirit Airlines
Fri 5/109:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 4/10$129
Mon 4/2210:00 pmORD - SJU
1 stop12h 38mSpirit Airlines
Wed 5/159:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 4/9$131
Tue 5/77:27 amORD - SJU
1 stop10h 35mSpirit Airlines
Thu 5/911:07 pmSJU - ORD
1 stop11h 48mSpirit Airlines
Deal found 4/10$133
Sun 4/2811:20 amORD - SJU
Nonstop4h 43mSpirit Airlines
Fri 5/39:32 pmSJU - ORD
1 stop12h 51mSpirit Airlines
Deal found 4/10$140
Mon 4/2210:00 pmORD - SJU
1 stop12h 38mSpirit Airlines
Tue 5/141:30 amSJU - ORD
2 stops22h 59mSpirit Airlines
Deal found 4/9$142

Cheap Frontier flights from Chicago to Puerto Rico

Explore cheap flight options specifically provided by Frontier for the route between Chicago and Puerto Rico. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
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 5/116:00 amORD - SJU
1 stop13h 14mFrontier
Mon 5/136:00 amSJU - ORD
1 stop29h 47mFrontier
Deal found 4/9$125
Tue 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/159:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/10$133
Mon 5/66:00 amORD - SJU
1 stop10h 56mFrontier
Wed 5/156:00 amSJU - ORD
1 stop16h 57mFrontier
Deal found 4/10$134
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 4/10$135
Tue 4/305:30 amORD - SJU
1 stop8h 54mFrontier
Sat 5/46:15 amSJU - ORD
1 stop18h 28mFrontier
Deal found 4/10$136
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Sat 5/188:17 pmSJU - MDW
1 stop29h 24mFrontier
Deal found 4/10$137
Tue 4/305:30 amORD - SJU
1 stop8h 54mFrontier
Fri 5/33:09 amSJU - ORD
1 stop21h 34mFrontier
Deal found 4/10$138
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Wed 5/158:15 pmSJU - MDW
1 stop29h 31mFrontier
Deal found 4/10$139
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Tue 5/79:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$140

Cheap Chicago to Puerto Rico flights in April & May 2024

Find cheap flight options from Chicago to Puerto Rico specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,194,136 searches. Prices were last updated on April 11, 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 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/159:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/10$133
Tue 4/302:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/89:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/10$134
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 4/10$135
Thu 4/252:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/18:15 pmSJU - MDW
1 stop27h 33mFrontier
Deal found 4/10$136
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Sat 5/188:17 pmSJU - MDW
1 stop29h 24mFrontier
Deal found 4/10$137
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Tue 5/79:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$138
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Wed 5/158:15 pmSJU - MDW
1 stop29h 31mFrontier
Deal found 4/10$139
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Tue 5/79:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$140
Fri 4/264:51 pmMDW - SJU
1 stop24h 04mFrontier
Wed 5/18:15 pmSJU - MDW
1 stop27h 33mFrontier
Deal found 4/10$145

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 3,194,136 searches. Data last updated April 11, 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 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/159:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/10$133
Tue 4/302:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/89:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/10$134
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 4/10$135
Thu 4/252:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/18:15 pmSJU - MDW
1 stop27h 33mFrontier
Deal found 4/10$136
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Sat 5/188:17 pmSJU - MDW
1 stop29h 24mFrontier
Deal found 4/10$137
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Tue 5/79:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$138
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Wed 5/158:15 pmSJU - MDW
1 stop29h 31mFrontier
Deal found 4/10$139
Sat 5/46:45 amMDW - SJU
1 stop12h 29mFrontier
Tue 5/79:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$140
Fri 4/264:51 pmMDW - SJU
1 stop24h 04mFrontier
Wed 5/18:15 pmSJU - MDW
1 stop27h 33mFrontier
Deal found 4/10$145

Non-stop flights to Puerto Rico from Chicago

Discover non-stop flight options from Chicago to Puerto Rico. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
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.
Sat 5/1811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 5/296:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$189
Wed 5/811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 5/146:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$195
Tue 4/3011:20 amORD - SJU
Nonstop4h 43mSpirit Airlines
Wed 5/86:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$196
Mon 4/2211:20 amORD - SJU
Nonstop4h 43mSpirit Airlines
Wed 5/226:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/9$197
Tue 5/1411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Sat 5/186:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$198
Mon 5/1311:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 5/156:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$199
Fri 5/1011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 5/146:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$204
Sun 5/511:20 amORD - SJU
Nonstop4h 43mSpirit Airlines
Wed 5/86:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$209
Sun 5/129:37 amORD - SJU
Nonstop4h 54mSpirit Airlines
Tue 5/146:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 4/10$211

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 3,194,136 searches. Data last updated April 11, 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.
Thu 4/252:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 5/18:15 pmSJU - MDW
1 stop27h 33mFrontier
Deal found 4/10$136
Thu 4/252:44 pmMDW - SJU
1 stop11h 39mFrontier
Sat 4/272:50 amSJU - MDW
1 stop10h 02mFrontier
Deal found 4/10$149
Fri 4/194:51 pmMDW - SJU
1 stop24h 04mFrontier
Wed 4/246:00 amSJU - MDW
1 stop16h 43mFrontier
Deal found 4/10$154
Tue 4/237:00 amMDW - SJU
2 stops24h 34mFrontier
Tue 4/309:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$157
Mon 4/227:17 pmMDW - SJU
1 stop12h 17mFrontier
Wed 5/159:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/9$166
Wed 4/177:00 amMDW - SJU
1 stop12h 31mFrontier
Wed 4/249:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/9$168
Fri 4/194:51 pmMDW - SJU
1 stop24h 04mFrontier
Tue 4/239:34 amSJU - MDW
2 stops30h 05mFrontier
Deal found 4/10$169
Tue 4/232:44 pmMDW - SJU
1 stop11h 39mFrontier
Wed 4/249:34 amSJU - MDW
1 stop9h 53mFrontier
Deal found 4/10$171
Thu 4/252:44 pmMDW - SJU
1 stop11h 39mFrontier
Tue 4/309:34 amSJU - MDW
1 stop9h 49mFrontier
Deal found 4/10$176

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 3,194,136 searches. Data last updated April 11, 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.
Thu 4/255:51 pmORD - BQN
1 stop6h 54mFrontier
Deal found 4/10$69
Wed 5/87:17 pmMDW - SJU
1 stop12h 17mFrontier
Deal found 4/11$69
Sat 4/273:54 pmMDW - SJU
1 stop15h 40mFrontier
Deal found 4/9$73
Sat 5/113:54 pmMDW - SJU
1 stop15h 40mFrontier
Deal found 4/10$74
Fri 4/267:17 pmMDW - SJU
1 stop12h 17mFrontier
Deal found 4/9$79
Fri 4/267:17 pmMDW - SJU
1 stop12h 17mFrontier
Deal found 4/10$80
Wed 5/157:17 pmMDW - SJU
1 stop28h 58mFrontier
Deal found 4/10$81
Fri 5/108:25 amORD - SJU
1 stop23h 24mFrontier
Deal found 4/10$89
Wed 5/18:32 amORD - SJU
1 stop11h 33mSpirit Airlines
Deal found 4/10$90

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 3,194,136 searches. Data last updated April 11, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$120 - $150

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/30

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Wed 5/8

1 stop13h 48m

$120

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/7

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Wed 5/15

1 stop8h 03m

$121

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/7

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Tue 5/21

1 stop13h 48m

$124

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/11

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Mon 5/13

1 stop29h 47m

$125

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/7

1 stop10h 35m

San Juan Luis Munoz Marin Intl

Tue 5/14

1 stop28h 32m

$126

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 5/14

1 stop11h 39m

San Juan Luis Munoz Marin Intl

Wed 5/15

1 stop9h 53m

$133

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/6

1 stop10h 56m

San Juan Luis Munoz Marin Intl

Wed 5/15

1 stop16h 57m

$134

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/27

1 stop13h 14m

San Juan Luis Munoz Marin Intl

Wed 5/1

1 stop9h 30m

$139

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 4/30

2 stops28h 54m

San Juan Luis Munoz Marin Intl

Wed 5/8

1 stop16h 43m

$150

Flights are sorted by cheapest first

Deals found on 4/10

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

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 April 11, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, Frontier and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
7.7
Good
4,730 reviews

Food

7.2

Comfort

7.9

Overall

7.7

Boarding

7.8

Crew

8.3

Entertainment

7.5

Reviews

1 / 10

It was a good flight. The crew were very nice. The delay in the takeoff was not JetBlue’s fault. However, the choice of snacks needs to change. Whatever happened to Animal Crackers or Popcorners, chocolate chip cookies, etc. The old choices were better. The deplaning process is always a mess. I wish JetBlue could fix it.

7.7
Good
4,730 reviews
7.7
Good
4,730 reviews

Food

7.2

Comfort

7.9

Overall

7.7

Boarding

7.8

Crew

8.3

Entertainment

7.5

Reviews

1 / 10

It was a good flight. The crew were very nice. The delay in the takeoff was not JetBlue’s fault. However, the choice of snacks needs to change. Whatever happened to Animal Crackers or Popcorners, chocolate chip cookies, etc. The old choices were better. The deplaning process is always a mess. I wish JetBlue could fix it.

7.4
Good
11,391 reviews
7.7
Good
4,730 reviews

Food

7.2

Comfort

7.9

Overall

7.7

Boarding

7.8

Crew

8.3

Entertainment

7.5

Reviews

1 / 10

It was a good flight. The crew were very nice. The delay in the takeoff was not JetBlue’s fault. However, the choice of snacks needs to change. Whatever happened to Animal Crackers or Popcorners, chocolate chip cookies, etc. The old choices were better. The deplaning process is always a mess. I wish JetBlue could fix it.

7.3
Good
15,011 reviews
7.7
Good
4,730 reviews

Food

7.2

Comfort

7.9

Overall

7.7

Boarding

7.8

Crew

8.3

Entertainment

7.5

Reviews

1 / 10

It was a good flight. The crew were very nice. The delay in the takeoff was not JetBlue’s fault. However, the choice of snacks needs to change. Whatever happened to Animal Crackers or Popcorners, chocolate chip cookies, etc. The old choices were better. The deplaning process is always a mess. I wish JetBlue could fix it.

6.4
Okay
8,803 reviews
7.7
Good
4,730 reviews

Food

7.2

Comfort

7.9

Overall

7.7

Boarding

7.8

Crew

8.3

Entertainment

7.5

Reviews

1 / 10

It was a good flight. The crew were very nice. The delay in the takeoff was not JetBlue’s fault. However, the choice of snacks needs to change. Whatever happened to Animal Crackers or Popcorners, chocolate chip cookies, etc. The old choices were better. The deplaning process is always a mess. I wish JetBlue could fix it.

6.3
Okay
4,202 reviews
7.7
Good
4,730 reviews

Food

7.2

Comfort

7.9

Overall

7.7

Boarding

7.8

Crew

8.3

Entertainment

7.5

Reviews

1 / 10

It was a good flight. The crew were very nice. The delay in the takeoff was not JetBlue’s fault. However, the choice of snacks needs to change. Whatever happened to Animal Crackers or Popcorners, chocolate chip cookies, etc. The old choices were better. The deplaning process is always a mess. I wish JetBlue could fix it.

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 $120, but on average you can expect to pay $132.

  • 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 $211.

  • 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 popular airlines that fly 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: American Airlines (89%), Alaska Airlines (89%), United Airlines( 81%).

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

    On average you can expect to pay $711 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $118.

  • 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 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 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 see available direct flights.

  • 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 do 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 4/10.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 3,194,136 searches. Data last updated April 11, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$262FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$129Average$314FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$142Average$536FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$153Average$527FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapest$164Average$461FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest$300Average$484FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights

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 April 11, 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

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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

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.

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

Millions of users choose and trust Cheapflights to book the best flight deals from Chicago to Puerto Rico for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Yes! Cheapflights helps users easily 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?

Not ready to book yet? You can track prices for flights from Chicago to Puerto Rico on Cheapflights with our Price Alert feature and get notified when better prices are available.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.