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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 6/10. 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
May 9 — May 161
From?
To?
Thu 5/9
Thu 5/16
1 adult, Economy
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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 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 2,864,334 searches. Data last updated May 4, 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 5/219:57 amORD - SJU
1 stop8h 00mSpirit Airlines
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mSpirit Airlines
Deal found 5/3$120
Tue 5/149:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Tue 5/215:59 pmSJU - ORD
2 stops23h 36mSpirit Airlines
Deal found 5/2$123
Tue 5/2110:58 amORD - SJU
1 stop7h 13mSpirit Airlines
Sat 5/2512:32 pmSJU - ORD
1 stop8h 01mSpirit Airlines
Deal found 5/3$124
Tue 5/219:57 amORD - SJU
1 stop8h 00mSpirit Airlines
Sat 5/256:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/3$134
Tue 5/219:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mSpirit Airlines
Deal found 5/3$135
Tue 5/216:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mSpirit Airlines
Deal found 5/4$137
Tue 6/49:15 pmORD - SJU
1 stop20h 50mSpirit Airlines
Tue 6/1112:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/3$142
Wed 5/225:00 amORD - SJU
1 stop11h 28mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
2 stops15h 01mSpirit Airlines
Deal found 5/3$143
Mon 6/35:00 amORD - SJU
1 stop12h 39mSpirit Airlines
Sat 6/812:41 pmSJU - ORD
1 stop9h 10mSpirit Airlines
Deal found 5/3$145

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 2,864,334 searches. Data last updated May 4, 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.
Fri 5/177:23 pmMDW - SJU
1 stop15h 38mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$143
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$146
Sat 5/185:45 pmMDW - SJU
1 stop14h 45mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$148
Tue 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$175
Mon 5/1310:37 amMDW - SJU
1 stop15h 46mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$188
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Tue 5/213:00 amSJU - MDW
1 stop28h 54mFrontier
Deal found 5/4$208
Tue 5/2110:16 amMDW - SJU
1 stop12h 38mFrontier
Wed 5/299:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/4$212
Mon 5/206:30 pmMDW - SJU
1 stop6h 28mFrontier
Sat 5/255:38 pmSJU - MDW
1 stop7h 31mFrontier
Deal found 5/4$213
Sat 5/189:08 pmMDW - SJU
1 stop10h 15mFrontier
Wed 5/299:19 amSJU - MDW
1 stop10h 08mFrontier
Deal found 5/4$214

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 2,864,334 searches. Prices were last updated on May 4, 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.
Sat 5/189:08 pmMDW - SJU
1 stop10h 15mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$137
Tue 5/2110:16 amMDW - SJU
1 stop12h 38mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$138
Mon 5/206:30 pmMDW - SJU
1 stop6h 28mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$139
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$147
Fri 5/177:23 pmMDW - SJU
1 stop15h 38mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$173
Tue 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$175
Wed 5/157:00 amMDW - SJU
1 stop12h 31mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$176
Wed 5/157:00 amMDW - SJU
1 stop12h 31mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$177
Sat 5/187:25 pmORD - SJU
2 stops25h 49mSpirit Airlines
Tue 5/219:07 pmSJU - ORD
1 stop20h 28mSpirit Airlines
Deal found 5/4$181

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 2,864,334 searches. Data last updated May 4, 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.
Sat 5/189:08 pmMDW - SJU
1 stop10h 15mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$137
Tue 5/2110:16 amMDW - SJU
1 stop12h 38mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$138
Mon 5/206:30 pmMDW - SJU
1 stop6h 28mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$139
Sun 5/197:23 pmMDW - SJU
1 stop12h 07mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$147
Fri 5/177:23 pmMDW - SJU
1 stop15h 38mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$173
Tue 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$175
Wed 5/157:00 amMDW - SJU
1 stop12h 31mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$176
Wed 5/157:00 amMDW - SJU
1 stop12h 31mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$177
Sat 5/187:25 pmORD - SJU
2 stops25h 49mSpirit Airlines
Tue 5/219:07 pmSJU - ORD
1 stop20h 28mSpirit Airlines
Deal found 5/4$181

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 2,864,334 searches. Data last updated May 4, 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.
Wed 6/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/4$157
Wed 6/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/126:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/3$158
Tue 6/411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/3$176
Tue 6/411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/3$177
Tue 6/411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/3$178
Tue 5/1411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Fri 5/176:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/3$182
Tue 5/1411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Sun 5/194:30 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/3$184
Wed 5/1511:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Sun 5/264:30 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/2$189
Tue 5/1411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Sun 5/264:30 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/2$193

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 2,864,334 searches. Data last updated May 4, 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.
Tue 5/142:44 pmMDW - SJU
1 stop11h 39mFrontier
Sat 5/1810:18 pmSJU - MDW
1 stop9h 36mFrontier
Deal found 5/4$175
Sat 5/119:35 pmORD - SJU
1 stop20h 22mSpirit Airlines
Wed 5/159:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/3$182
Tue 5/1411:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Sun 5/194:30 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/3$184
Mon 5/139:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Mon 5/209:07 pmSJU - ORD
1 stop27h 22mSpirit Airlines
Deal found 5/3$185
Tue 5/149:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Fri 5/176:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/4$186
Mon 5/139:25 pmORD - SJU
2 stops13h 07mSpirit Airlines
Wed 5/151:32 pmSJU - ORD
1 stop8h 03mSpirit Airlines
Deal found 5/2$187
Mon 5/1310:37 amMDW - SJU
1 stop15h 46mFrontier
Wed 5/226:48 amSJU - MDW
1 stop16h 05mFrontier
Deal found 5/4$188
Tue 5/149:15 pmORD - SJU
1 stop20h 42mSpirit Airlines
Sat 5/253:30 amSJU - ORD
1 stop19h 42mSpirit Airlines
Deal found 5/2$189
Tue 5/149:15 pmORD - SJU
1 stop20h 42mMultiple Airlines
Mon 5/2012:59 amSJU - ORD
1 stop10h 54mMultiple Airlines
Deal found 5/2$190

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 2,864,334 searches. Data last updated May 4, 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 6/105:05 amORD - SJU
1 stop11h 06mSpirit Airlines
Deal found 5/2$87
Tue 6/45:00 amORD - SJU
2 stops21h 05mSpirit Airlines
Deal found 5/3$89
Tue 6/410:58 amORD - SJU
3 stops31h 07mSpirit Airlines
Deal found 5/4$91
Mon 6/35:00 amORD - SJU
2 stops15h 19mSpirit Airlines
Deal found 5/4$93
Mon 6/35:00 amORD - SJU
2 stops21h 05mSpirit Airlines
Deal found 5/2$94
Sat 5/259:35 pmORD - SJU
1 stop20h 22mSpirit Airlines
Deal found 5/3$95
Wed 5/156:16 pmORD - SJU
1 stop6h 54mSpirit Airlines
Deal found 5/3$96
Tue 5/710:00 pmORD - SJU
1 stop13h 41mSpirit Airlines
Deal found 5/3$97
Mon 5/139:25 pmORD - SJU
2 stops20h 46mSpirit Airlines
Deal found 5/3$98

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 2,864,334 searches. Data last updated May 4, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$120 - $172

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/21

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Sat 5/25

1 stop9h 00m

$120

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/14

1 stop20h 42m

San Juan Luis Munoz Marin Intl

Tue 5/21

2 stops23h 36m

$123

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/21

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Sat 5/25

1 stop8h 01m

$124

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 5/21

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Sat 5/25

Nonstop5h 10m

$134

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/17

1 stop15h 38m

San Juan Luis Munoz Marin Intl

Sat 5/18

1 stop9h 36m

$143

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sun 5/19

1 stop12h 07m

San Juan Luis Munoz Marin Intl

Wed 5/22

1 stop16h 05m

$146

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 5/18

1 stop14h 45m

San Juan Luis Munoz Marin Intl

Wed 5/22

1 stop16h 05m

$148

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/18

1 stop15h 51m

San Juan Luis Munoz Marin Intl

Tue 5/28

1 stop14h 58m

$168

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/18

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Sun 5/26

1 stop11h 48m

$172

Flights are sorted by cheapest first

Deals found on 5/3

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 May 4, 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.
United Airlines
7.4
Good
11,125 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.2

Crew

8.1

Food

6.7

Reviews

1 / 10

The staff were pleasant. There was no food or entertainment.

United Airlines
7.4
Good
11,125 reviews
United Airlines
7.4
Good
11,125 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.2

Crew

8.1

Food

6.7

Reviews

1 / 10

The staff were pleasant. There was no food or entertainment.

American Airlines
7.3
Good
14,728 reviews
United Airlines
7.4
Good
11,125 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.2

Crew

8.1

Food

6.7

Reviews

1 / 10

The staff were pleasant. There was no food or entertainment.

Spirit Airlines
6.4
Okay
8,728 reviews
United Airlines
7.4
Good
11,125 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.2

Crew

8.1

Food

6.7

Reviews

1 / 10

The staff were pleasant. There was no food or entertainment.

Frontier
6.3
Okay
4,098 reviews
United Airlines
7.4
Good
11,125 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.2

Crew

8.1

Food

6.7

Reviews

1 / 10

The staff were pleasant. There was no food or entertainment.

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 $141.

  • 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 $192.

  • 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: American Airlines (94%), Alaska Airlines (93%), United Airlines( 84%).

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

    On average you can expect to pay $797 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $78 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $116.

  • 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 5/4.

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.

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
Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Nassau flights
O'Hare Intl to Simpson Bay flights
Midway to Oranjestad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Castries flights
St. Louis to Punta Cana flights
O'Hare Intl to Christiansted flights
Midway to Saint Thomas Island flights
St. Louis to Montego Bay flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Willemstad flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to George Town flights
Midway to Providenciales flights
Midway to Simpson Bay flights
Midway to Nassau flights
O'Hare Intl to Kingston flights
O'Hare Intl to Puerto Plata flights
Midway to Santo Domingo flights
O'Hare Intl to Kingstown flights
St. Louis to Providenciales flights
St. Louis to George Town flights
O'Hare Intl to St. John's flights
St. Louis to Nassau flights
O'Hare Intl to Aguadilla flights
St. Louis to Oranjestad flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to Kingston flights
O'Hare Intl to St. George's flights
O'Hare Intl to Havana flights
St. Louis to Bridgetown flights
St. Louis to Willemstad flights
St. Louis to Puerto Plata flights
St. Louis to Christiansted flights
Midway to George Town flights
O'Hare Intl to Basseterre flights
Midway to Castries flights
St. Louis to Simpson Bay flights
St. Louis to Castries flights
O'Hare Intl to Castries flights

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 2,864,334 searches. Data last updated May 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$261FlexibilityNo cancel feeOn-time62%
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Spirit AirlinesCheapest$133Average$315FlexibilityNo cancel feeOn-time65%
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DeltaCheapest$140Average$533FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapest$153Average$491FlexibilityNo cancel feeOn-time69%
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JetBlueCheapest$171Average$463FlexibilityNo cancel feeOn-time62%
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Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
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American AirlinesCheapest$308Average$486FlexibilityNo cancel feeOn-time71%
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Find flights from Chicago to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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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 4, 2024.
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100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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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.

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