HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Chicago (CHI) to Puerto Rico from $74

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 6/5. 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 27 — Jun 31
From?
To?
Mon 5/27
Mon 6/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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

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

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

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

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

Cheap Spirit Airlines flights from Chicago to Puerto Rico

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 2,730,072 searches. Data last updated May 22, 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
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/22$126
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/21$127
Tue 9/105:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Tue 9/177:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Deal found 5/21$137
Tue 9/176:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Tue 9/247:57 pmSJU - ORD
1 stop21h 43mSpirit Airlines
Deal found 5/22$138
Tue 8/205:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Tue 8/277:57 pmSJU - ORD
2 stops23h 29mSpirit Airlines
Deal found 5/21$149
Tue 8/205:35 pmORD - SJU
3 stops24h 22mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/21$151
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/21$152
Tue 9/175:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Tue 9/241:32 pmSJU - ORD
2 stops21h 01mSpirit Airlines
Deal found 5/22$153
Tue 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/21$154

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 2,730,072 searches. Data last updated May 22, 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.
Thu 5/301:30 pmORD - SJU
1 stop10h 46mFrontier
Sun 6/28:32 pmSJU - ORD
1 stop29h 36mFrontier
Deal found 5/20$244
Sat 6/157:49 amMDW - SJU
1 stop23h 51mFrontier
Sat 6/2210:15 pmSJU - MDW
1 stop12h 16mFrontier
Deal found 5/20$252
Mon 9/2310:00 amMDW - SJU
1 stop10h 47mFrontier
Mon 9/231:25 amSJU - MDW
1 stop9h 44mFrontier
Deal found 5/21$253
Tue 9/1010:00 amMDW - SJU
1 stop10h 47mFrontier
Tue 9/1710:47 pmSJU - MDW
1 stop13h 08mFrontier
Deal found 5/21$258
Thu 5/301:30 pmORD - SJU
1 stop10h 46mFrontier
Sat 6/13:02 amSJU - ORD
1 stop23h 06mFrontier
Deal found 5/20$267
Fri 9/2010:00 amMDW - SJU
1 stop10h 47mFrontier
Tue 9/2410:47 pmSJU - MDW
1 stop13h 08mFrontier
Deal found 5/21$268
Thu 8/89:04 pmMDW - SJU
1 stop10h 22mFrontier
Tue 8/1310:47 pmSJU - MDW
1 stop13h 46mFrontier
Deal found 5/21$270
Sat 6/12:35 pmMDW - SJU
1 stop8h 24mFrontier
Wed 6/59:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/21$271
Sat 8/318:13 pmMDW - SJU
1 stop11h 34mFrontier
Wed 9/410:47 pmSJU - MDW
1 stop13h 08mFrontier
Deal found 5/21$274

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 2,730,072 searches. Prices were last updated on May 22, 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 5/286:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Tue 6/47:57 pmSJU - ORD
1 stop15h 04mSpirit Airlines
Deal found 5/21$129
Tue 5/285:41 pmORD - SJU
1 stop16h 51mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/21$146
Tue 5/286:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/21$148
Wed 6/58:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Wed 6/128:06 pmSJU - ORD
1 stop29h 49mSpirit Airlines
Deal found 5/21$152
Tue 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/21$154
Wed 5/296:40 pmORD - SJU
1 stop15h 52mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/21$157
Tue 6/49:15 pmORD - SJU
1 stop14h 47mSpirit Airlines
Wed 6/59:06 pmSJU - ORD
2 stops24h 41mSpirit Airlines
Deal found 5/21$161
Wed 5/295:00 amORD - SJU
1 stop11h 28mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/21$166
Tue 5/285:41 pmORD - SJU
1 stop16h 51mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/21$168

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 2,730,072 searches. Data last updated May 22, 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 8/205:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/22$126
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/21$127
Tue 5/286:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Tue 6/47:57 pmSJU - ORD
1 stop15h 04mSpirit Airlines
Deal found 5/21$129
Tue 9/105:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Tue 9/177:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Deal found 5/21$137
Tue 9/176:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Tue 9/247:57 pmSJU - ORD
1 stop21h 43mSpirit Airlines
Deal found 5/22$138
Tue 5/285:41 pmORD - SJU
1 stop16h 51mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/21$146
Tue 5/286:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Deal found 5/21$148
Tue 8/205:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Tue 8/277:57 pmSJU - ORD
2 stops23h 29mSpirit Airlines
Deal found 5/21$149
Tue 8/205:35 pmORD - SJU
3 stops24h 22mSpirit Airlines
Sat 8/2412:28 pmSJU - ORD
1 stop9h 04mSpirit Airlines
Deal found 5/21$151

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 2,730,072 searches. Data last updated May 22, 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 8/1010:26 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Tue 8/204:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/21$195
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/53:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/21$199
Tue 8/2011:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Mon 8/266:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/21$202
Tue 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Sat 6/154:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/21$209
Tue 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/186:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/21$213
Tue 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Sun 6/166:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/21$216
Tue 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 6/253:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/21$217
Fri 7/510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Sat 7/134:26 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Deal found 5/21$218
Wed 6/1210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/266:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/20$225

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 2,730,072 searches. Data last updated May 22, 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.
Wed 5/295:00 amORD - SJU
1 stop11h 28mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
3 stops22h 58mSpirit Airlines
Deal found 5/21$190
Fri 5/315:01 amORD - SJU
1 stop13h 13mMultiple Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mMultiple Airlines
Deal found 5/21$191
Wed 5/296:40 pmORD - SJU
1 stop15h 52mSpirit Airlines
Wed 6/269:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/21$198
Thu 5/3011:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Wed 6/53:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/21$199
Wed 5/297:20 amORD - SJU
2 stops27h 12mSpirit Airlines
Mon 6/39:07 pmSJU - ORD
2 stops19h 51mSpirit Airlines
Deal found 5/21$200
Tue 5/281:30 pmORD - SJU
1 stop11h 28mMultiple Airlines
Tue 6/47:57 pmSJU - ORD
1 stop15h 04mMultiple Airlines
Deal found 5/21$201
Tue 5/285:41 pmORD - SJU
1 stop16h 51mSpirit Airlines
Tue 6/47:57 pmSJU - ORD
2 stops21h 10mSpirit Airlines
Deal found 5/21$203
Tue 5/286:32 amORD - SJU
1 stop28h 11mSpirit Airlines
Wed 5/299:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/21$204
Fri 5/3111:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Tue 6/49:07 pmSJU - ORD
1 stop13h 54mSpirit Airlines
Deal found 5/21$205

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 2,730,072 searches. Data last updated May 22, 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.
Wed 6/58:27 amMDW - SJU
1 stop9h 38mMultiple Airlines
Deal found 5/21$74
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Deal found 5/21$86
Tue 6/187:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/21$87
Thu 7/46:40 pmORD - SJU
1 stop15h 50mSpirit Airlines
Deal found 5/21$88
Mon 6/37:23 pmMDW - SJU
1 stop21h 35mFrontier
Deal found 5/22$88
Tue 6/1110:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/21$89
Wed 6/57:40 amORD - SJU
2 stops18h 30mSpirit Airlines
Deal found 5/21$91
Wed 6/56:15 pmORD - SJU
1 stop12h 54mMultiple Airlines
Deal found 5/21$92
Mon 6/1710:27 amORD - SJU
1 stop7h 38mSpirit Airlines
Deal found 5/21$93

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 2,730,072 searches. Data last updated May 22, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$126 - $380

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

Sat 8/24

1 stop9h 04m

$126

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Sat 8/24

1 stop9h 04m

$127

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Tue 9/17

1 stop14h 36m

$137

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/17

1 stop15h 56m

San Juan Luis Munoz Marin Intl

Tue 9/24

1 stop21h 43m

$138

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Tue 8/27

2 stops23h 29m

$149

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 9/20

1 stop16h 53m

San Juan Luis Munoz Marin Intl

Mon 9/23

1 stop11h 21m

$246

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/15

1 stop23h 51m

San Juan Luis Munoz Marin Intl

Sat 6/22

1 stop12h 16m

$252

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 8/13

1 stop6h 29m

San Juan Luis Munoz Marin Intl

Tue 8/20

1 stop10h 44m

$369

Chicago O'Hare IntlPonce Mercedita

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Tue 6/11

1 stop8h 08m

Ponce Mercedita

Sat 6/15

1 stop7h 20m

$380

Flights are sorted by cheapest first

Deals found on 5/22

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 22, 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
10,585 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

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
10,585 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

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
4,426 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

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.

Avelo Airlines
7.5
Good
68 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

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
10,870 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

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
14,421 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

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 $126, but on average you can expect to pay $155.

  • 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 $223.

  • 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 $602 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $103 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $125.

  • 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 5/22.

  • 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.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $248). 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

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.

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 Saint Thomas Island flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Nassau flights
Midway to Saint Thomas Island flights
O'Hare Intl to Providenciales flights
Midway to Oranjestad flights
St. Louis to Punta Cana flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Bridgetown flights
St. Louis to Montego Bay flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Simpson Bay flights
O'Hare Intl to Castries flights
O'Hare Intl to Kingston flights
Midway to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Christiansted flights
O'Hare Intl to George Town flights
Midway to Providenciales flights
Midway to Santo Domingo flights
St. Louis to Nassau flights
St. Louis to Santiago de los Caballeros flights
O'Hare Intl to St. John's flights
O'Hare Intl to Puerto Plata flights
St. Louis to Providenciales flights
Midway to Kingston flights
St. Louis to George Town flights
O'Hare Intl to St. George's flights
St. Louis to Oranjestad flights
O'Hare Intl to Basseterre flights
Midway to George Town flights
O'Hare Intl to Havana flights
St. Louis to Bridgetown flights
St. Louis to Willemstad flights
O'Hare Intl to Port of Spain flights
St. Louis to Simpson Bay flights
O'Hare Intl to Santiago de los Caballeros flights
Moline to Oranjestad flights
St. Louis to Christiansted flights
O'Hare Intl to Aguadilla flights
Evansville to Luis Munoz Marin Intl flights
O'Hare Intl to Kingstown 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 2,730,072 searches. Data last updated May 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$263FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$132Average$307FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$136Average$554FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$153Average$506FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapest$172Average$461FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
American AirlinesCheapest$301Average$485FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Newark Airport to West Palm Beach flights
Charlotte to Newark Airport flights
New York to New Jersey flights
Albuquerque to Phoenix flights
Detroit to Toronto flights
Boston to London flights
New York to Tokyo flights
Orlando to Detroit flights
Bellingham to Las Vegas flights
Dallas to Hyderabad flights
Los Angeles to New York flights
Chicago to San Juan 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.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Chicago to Puerto Rico

Find hourly flight availability from Chicago to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 22, 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

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Neiva La Marguita
Flights to Hyannis Barnstable
Flights to Laayoune Hassan I
Flights to Edremit/Korfez
Flights to Vava'u Lupepau'U
Flights to Surigao
Flights to Melilla
Flights to Virac
Flights to Rhinelander Oneida County
Flights to Cornwall Newquay
Flights to Parikia Paros
Flights to Cortez Montezuma County
Flights to Mason City
Flights to Ningbo Lishe Intl
Flights to Miyakojima Hirara
Flights to Kirkwall Arpt
Flights to Girona Costa Brava
Flights to Provincetown
Flights to Perugia Sant Egidio
Flights to Samos
Flights to Constanţa Mihail Kogalniceanu
Flights to Dharamshala Kangra
Flights to Dalaman
Flights to Pellston Emmet County

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.
View all available airlines