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Cheap flights from Chicago (CHI) to Puerto Rico from $46

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 8/27. 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 4 — Jun 111
From?
To?
Tue 6/4
Tue 6/11
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 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 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 2,784,634 searches. Data last updated May 30, 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 8/205:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/30$113
Tue 8/2010:33 amORD - SJU
1 stop7h 36mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/30$116
Tue 8/2010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/30$120
Tue 9/107:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Tue 9/247:57 pmSJU - ORD
1 stop29h 03mSpirit Airlines
Deal found 5/29$121
Tue 8/277:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Tue 8/271:00 amSJU - ORD
2 stops17h 27mSpirit Airlines
Deal found 5/29$122
Tue 8/2710:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Wed 8/286:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$123
Mon 9/96:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Wed 9/117:57 pmSJU - ORD
1 stop22h 30mSpirit Airlines
Deal found 5/29$124
Mon 9/95:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Wed 9/116:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$125
Tue 8/277:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Wed 8/2812:28 pmSJU - ORD
1 stop7h 29mSpirit Airlines
Deal found 5/29$127

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 2,784,634 searches. Data last updated May 30, 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 6/89:31 amMDW - SJU
1 stop16h 37mFrontier
Wed 6/129:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/30$195
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Wed 6/1210:15 pmSJU - MDW
2 stops22h 41mFrontier
Deal found 5/30$201
Fri 6/75:58 pmORD - SJU
1 stop15h 45mFrontier
Tue 6/113:08 amSJU - ORD
1 stop23h 00mFrontier
Deal found 5/30$213
Wed 6/58:27 amMDW - SJU
1 stop17h 41mFrontier
Wed 6/126:00 amSJU - MDW
1 stop8h 32mFrontier
Deal found 5/30$225
Sat 6/89:31 amMDW - SJU
1 stop16h 37mFrontier
Wed 6/1210:15 pmSJU - MDW
2 stops22h 41mFrontier
Deal found 5/30$231
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Wed 6/123:08 amSJU - MDW
1 stop7h 23mFrontier
Deal found 5/30$236
Thu 6/62:36 pmMDW - SJU
1 stop16h 33mFrontier
Sat 6/85:57 pmSJU - MDW
1 stop16h 34mFrontier
Deal found 5/29$241
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Thu 6/139:30 amSJU - MDW
2 stops11h 26mFrontier
Deal found 5/30$244
Fri 6/75:58 pmORD - SJU
1 stop15h 45mFrontier
Tue 6/113:08 amSJU - ORD
1 stop23h 00mFrontier
Deal found 5/30$247

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 2,784,634 searches. Prices were last updated on May 30, 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.
Wed 6/128:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Mon 6/1712:30 pmSJU - ORD
1 stop20h 51mSpirit Airlines
Deal found 5/29$193
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sun 6/1611:08 pmSJU - ORD
1 stop11h 53mSpirit Airlines
Deal found 5/29$194
Wed 6/265:05 amORD - SJU
1 stop11h 25mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/30$195
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/30$195
Sat 6/85:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Tue 6/112:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/29$196
Wed 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 7/39:06 pmSJU - ORD
1 stop28h 49mSpirit Airlines
Deal found 5/29$197
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/25:40 amSJU - ORD
2 stops16h 07mSpirit Airlines
Deal found 5/29$198
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/30$199
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Fri 7/57:06 pmSJU - ORD
1 stop6h 49mSpirit Airlines
Deal found 5/28$200

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 2,784,634 searches. Data last updated May 30, 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.
Mon 9/169:25 pmORD - SJU
2 stops13h 03mSpirit Airlines
Sat 9/215:51 amSJU - ORD
2 stops13h 44mSpirit Airlines
Deal found 5/29$192
Wed 6/128:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Mon 6/1712:30 pmSJU - ORD
1 stop20h 51mSpirit Airlines
Deal found 5/29$193
Thu 9/511:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Mon 9/95:51 amSJU - ORD
1 stop27h 42mSpirit Airlines
Deal found 5/29$194
Wed 9/119:04 pmORD - SJU
1 stop28h 51mSpirit Airlines
Fri 9/205:51 amSJU - ORD
1 stop27h 42mSpirit Airlines
Deal found 5/29$195
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/30$195
Mon 7/110:27 amORD - SJU
1 stop7h 38mSpirit Airlines
Wed 7/1012:44 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Deal found 5/29$196
Wed 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 7/39:06 pmSJU - ORD
1 stop28h 49mSpirit Airlines
Deal found 5/29$197
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/25:40 amSJU - ORD
2 stops16h 07mSpirit Airlines
Deal found 5/29$198
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/30$199

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 2,784,634 searches. Data last updated May 30, 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.
Tue 6/259:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 7/23:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/29$201
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sat 8/246:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$202
Wed 8/2111:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Sat 8/246:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/28$203
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Thu 7/46:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/29$204
Fri 8/2311:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 8/276:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$206
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sun 6/166:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/29$207
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sun 6/166:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/29$209
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/30$214
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Fri 7/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/28$216

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 2,784,634 searches. Data last updated May 30, 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.
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/30$195
Sat 6/85:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Tue 6/112:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/29$196
Thu 6/65:34 pmORD - SJU
1 stop7h 59mSpirit Airlines
Wed 6/122:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 5/30$201
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Wed 6/1210:15 pmSJU - MDW
2 stops22h 41mFrontier
Deal found 5/30$201
Fri 6/710:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/129:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/29$204
Sat 6/83:56 pmORD - SJU
1 stop27h 29mSpirit Airlines
Wed 6/122:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 5/29$206
Wed 6/58:50 pmORD - SJU
3 stops28h 43mSpirit Airlines
Wed 6/122:00 pmSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/29$208
Sat 6/89:41 pmORD - SJU
1 stop21h 44mSpirit Airlines
Fri 6/1412:10 pmSJU - ORD
1 stop12h 11mSpirit Airlines
Deal found 5/29$209
Fri 6/75:58 pmORD - SJU
1 stop15h 45mFrontier
Tue 6/113:08 amSJU - ORD
1 stop23h 00mFrontier
Deal found 5/30$213

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 2,784,634 searches. Data last updated May 30, 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.
Tue 8/275:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Deal found 5/28$46
Mon 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/28$56
Tue 6/118:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Deal found 5/28$57
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Deal found 5/30$62
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Deal found 5/29$63
Tue 8/275:00 amORD - SJU
2 stops18h 02mSpirit Airlines
Deal found 5/28$65
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Deal found 5/30$69
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/29$70
Wed 8/215:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Deal found 5/29$73

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 2,784,634 searches. Data last updated May 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$113 - $369

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

$113

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$116

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$120

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 9/24

1 stop29h 03m

$121

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/27

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 8/27

2 stops17h 27m

$122

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/27

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Wed 8/28

Nonstop5h 14m

$123

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/27

1 stop13h 11m

San Juan Luis Munoz Marin Intl

Sat 8/31

1 stop11h 50m

$191

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/8

1 stop16h 37m

San Juan Luis Munoz Marin Intl

Wed 6/12

1 stop9h 24m

$195

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/8

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Wed 8/14

1 stop8h 16m

$369

Flights are sorted by cheapest first

Deals found on 5/30

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 May 30, 2024.
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
10,457 reviews
Check prices

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.0

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
10,457 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.0

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.

JetBlue
7.6
Good
4,365 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.0

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.

United Airlines
7.4
Good
10,777 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.0

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.

American Airlines
7.3
Good
14,284 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.0

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.

Spirit Airlines
6.4
Okay
8,616 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Boarding

8.2

Entertainment

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Overall

8.0

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.

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 $113, but on average you can expect to pay $128.

  • Are there nonstop flights from Chicago to Puerto Rico for under $300 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $300. A good price for a nonstop flight from Chicago to Puerto Rico is less than $218.

  • 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 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 $600 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $105 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $115.

  • 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 5/30.

  • 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 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 $247). 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.

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
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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 2,784,634 searches. Data last updated May 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$262FlexibilityNo cancel feeOn-time62%
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Spirit AirlinesCheapest$130Average$309FlexibilityNo cancel feeOn-time65%
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DeltaCheapest$135Average$555FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapest$152Average$490FlexibilityNo cancel feeOn-time69%
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JetBlueCheapest$172Average$445FlexibilityNo cancel feeOn-time62%
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Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
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American AirlinesCheapest$301Average$485FlexibilityNo cancel feeOn-time71%
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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.
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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 30, 2024.
1%of flight departuresEarly morningMidnight to 6 am
93%of flight departuresMorning6 am to noon
6%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
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6 PM

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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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