Cheap flights from Puerto Rico to Chicago (CHI) from $62

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 6/4. 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.
SJU — CHI
May 29 — Jun 51

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

To save up to 85% on this flight, we recommend booking at least 16 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Puerto Rico to Chicago from $238 1-2 weeks out and tickets from $312 for flights departing within the next 72 hours.

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

Our data shows that January tends to be the cheapest month to fly to Chicago from Puerto Rico. Users have commonly found prices around $269 for the month, but tickets can be as low as $122. Due to multiple factors, prepare for potentially higher prices in March.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Puerto Rico to Chicago as you normally would.

Cheap United Airlines flights from Puerto Rico to Chicago

Explore cheap flight options specifically provided by United Airlines for the route between Puerto Rico and Chicago. 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 2,725,499 searches. Data last updated May 24, 2024.
Find some of the cheapest United Airlines flights traveling from Puerto Rico to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Thu 10/172:20 pmSJU - ORD
Nonstop5h 03mUnited Airlines
Mon 10/289:00 amORD - SJU
Nonstop4h 38mUnited Airlines
Deal found 5/23$275
Wed 10/164:25 pmSJU - ORD
1 stop8h 12mUnited Airlines
Mon 10/289:00 amORD - SJU
Nonstop4h 38mUnited Airlines
Deal found 5/23$280
Sat 10/194:55 pmSJU - ORD
1 stop7h 19mUnited Airlines
Tue 10/298:49 amORD - SJU
1 stop10h 37mUnited Airlines
Deal found 5/23$284
Thu 10/172:20 pmSJU - ORD
Nonstop5h 03mUnited Airlines
Thu 10/247:35 amORD - SJU
1 stop12h 00mUnited Airlines
Deal found 5/23$302
Thu 10/174:55 pmSJU - ORD
1 stop7h 19mUnited Airlines
Wed 10/237:35 amORD - SJU
1 stop12h 00mUnited Airlines
Deal found 5/23$306
Fri 5/311:05 amSJU - ORD
1 stop7h 55mUnited Airlines
Sat 6/86:07 pmORD - SJU
Nonstop4h 47mUnited Airlines
Deal found 5/22$420
Fri 5/313:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Thu 6/68:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/23$429
Tue 5/283:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Thu 5/308:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/22$484
Fri 5/313:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Thu 6/68:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/22$524

Cheap Spirit Airlines flights from Puerto Rico to Chicago

Explore cheap flight options specifically provided by Spirit Airlines for the route between Puerto Rico and Chicago. 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 2,725,499 searches. Data last updated May 24, 2024.
Take a gander at the lowest prices we've found on Spirit Airlines flights from Puerto Rico to Chicago. Check back soon if you're not seeing flights that suit your needs.
Wed 9/117:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Mon 9/235:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/23$144
Wed 9/115:51 amSJU - ORD
2 stops14h 06mSpirit Airlines
Mon 9/235:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/23$146
Thu 9/57:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Mon 9/95:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/23$150
Thu 8/2210:59 pmSJU - ORD
1 stop11h 34mSpirit Airlines
Mon 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/23$152
Wed 9/115:51 amSJU - ORD
2 stops14h 06mSpirit Airlines
Mon 9/239:25 pmORD - SJU
2 stops13h 03mSpirit Airlines
Deal found 5/23$155
Thu 9/126:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/175:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/23$159
Tue 6/118:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Wed 6/198:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Deal found 5/23$162
Wed 6/129:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Wed 6/198:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Deal found 5/23$164
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Tue 6/259:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/22$167

Cheap Puerto Rico to Chicago flights in May & June 2024

Find cheap flight options from Puerto Rico to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,725,499 searches. Prices were last updated on May 24, 2024.
Scroll through some of the best deals on flights from Puerto Rico to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Mon 6/105:34 pmORD - SJU
1 stop19h 33mSpirit Airlines
Deal found 5/22$154
Tue 6/1112:41 pmSJU - ORD
1 stop20h 40mSpirit Airlines
Tue 6/187:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/22$155
Tue 6/1112:41 pmSJU - ORD
1 stop20h 40mSpirit Airlines
Mon 6/175:34 pmORD - SJU
1 stop19h 33mSpirit Airlines
Deal found 5/22$162
Wed 6/129:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Wed 6/198:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Deal found 5/23$164
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Tue 6/259:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/22$167
Tue 6/1112:41 pmSJU - ORD
1 stop20h 40mSpirit Airlines
Mon 6/175:34 pmORD - SJU
1 stop24h 31mSpirit Airlines
Deal found 5/23$175
Fri 6/71:26 pmSJU - ORD
1 stop7h 00mSpirit Airlines
Sun 6/910:27 amORD - SJU
1 stop8h 58mSpirit Airlines
Deal found 5/22$177
Tue 6/1112:41 pmSJU - ORD
1 stop20h 40mSpirit Airlines
Tue 6/189:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/22$182
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Thu 6/209:24 amORD - SJU
1 stop10h 01mSpirit Airlines
Deal found 5/23$183

Puerto Rico to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Puerto Rico and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,725,499 searches. Data last updated May 24, 2024.
Scroll through some of the best deals on flights from Puerto Rico to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Tue 6/1112:41 pmSJU - ORD
1 stop20h 40mSpirit Airlines
Mon 6/175:34 pmORD - SJU
1 stop24h 31mSpirit Airlines
Deal found 5/23$175
Thu 9/126:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 9/165:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/23$176
Tue 9/101:00 amSJU - ORD
2 stops18h 26mSpirit Airlines
Mon 9/235:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/23$177
Tue 6/412:32 pmSJU - ORD
1 stop10h 24mSpirit Airlines
Thu 6/69:24 amORD - SJU
1 stop8h 41mSpirit Airlines
Deal found 5/23$178
Wed 9/116:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 9/2311:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/23$181
Fri 5/319:00 pmSJU - ORD
3 stops23h 33mSpirit Airlines
Tue 6/118:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Deal found 5/23$182
Tue 6/189:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Thu 6/209:24 amORD - SJU
1 stop10h 01mSpirit Airlines
Deal found 5/23$183
Wed 8/141:06 pmSJU - ORD
1 stop9h 42mSpirit Airlines
Mon 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/23$185
Tue 6/119:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Mon 6/179:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/23$188

Non-stop flights to Chicago from Puerto Rico

Discover non-stop flight options from Puerto Rico to Chicago. 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 2,725,499 searches. Data last updated May 24, 2024.
Take a look at some of the direct flights traveling from Puerto Rico to Chicago in the near future. Users can also choose from other Puerto Rico to Chicago flights by using the search form above.
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/1711:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/22$177
Wed 9/116:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 9/2311:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/23$181
Thu 9/126:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/1711:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/22$182
Thu 6/204:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/23$195
Tue 6/116:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Mon 6/1710:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/23$196
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/89:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/22$197
Sat 6/86:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/22$199
Tue 8/204:01 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Mon 8/269:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/22$200
Wed 8/146:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 8/2611:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/23$201

Puerto Rico to Chicago flights leaving soon

Find last-minute flight options from Puerto Rico to Chicago 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 2,725,499 searches. Data last updated May 24, 2024.
Have a look at some of the flights available from Puerto Rico to Chicago departing last-minute. To prevent any unwanted surprises, users should verify their flight info before booking.
Thu 5/3011:07 pmSJU - ORD
1 stop11h 48mSpirit Airlines
Wed 6/1210:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/22$225
Fri 5/319:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Thu 6/69:24 amORD - SJU
1 stop8h 41mSpirit Airlines
Deal found 5/23$228
Wed 5/299:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Mon 6/36:53 pmORD - SJU
1 stop21h 16mSpirit Airlines
Deal found 5/22$231
Fri 5/316:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Thu 6/69:24 amORD - SJU
1 stop8h 41mSpirit Airlines
Deal found 5/23$234
Fri 5/319:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Mon 6/36:53 pmORD - SJU
1 stop21h 16mSpirit Airlines
Deal found 5/22$245
Sat 6/16:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Sat 6/89:41 pmORD - SJU
1 stop21h 44mSpirit Airlines
Deal found 5/22$248
Sun 6/24:30 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Sat 6/295:18 pmORD - SJU
1 stop17h 12mSpirit Airlines
Deal found 5/23$250
Fri 5/316:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Mon 6/36:53 pmORD - SJU
1 stop21h 16mSpirit Airlines
Deal found 5/22$251
Tue 5/281:32 pmSJU - ORD
1 stop8h 03mSpirit Airlines
Tue 6/49:57 amORD - SJU
1 stop8h 00mSpirit Airlines
Deal found 5/23$253

One-way flights to Chicago from Puerto Rico

Search for one-way flight options from Puerto Rico to Chicago. 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 2,725,499 searches. Data last updated May 24, 2024.
Users traveling one-way from Puerto Rico to Chicago can select one of these great deals. Users can also find round-trip Puerto Rico to Chicago flights by using the search form above.
Tue 6/47:57 pmSJU - ORD
1 stop15h 04mSpirit Airlines
Deal found 5/22$62
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/22$63
Tue 6/1112:41 pmSJU - ORD
1 stop10h 17mSpirit Airlines
Deal found 5/22$67
Wed 6/55:40 amSJU - ORD
2 stops14h 25mSpirit Airlines
Deal found 5/23$68
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/22$69
Wed 8/2112:28 pmSJU - ORD
1 stop7h 29mSpirit Airlines
Deal found 5/22$72
Tue 6/47:57 pmSJU - ORD
2 stops21h 10mSpirit Airlines
Deal found 5/22$75
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/22$81
Wed 6/55:40 amSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/23$82

Find flights from Puerto Rico to Chicago within your budget

Customize your flight search to find flights from Puerto Rico to Chicago 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 2,725,499 searches. Data last updated May 24, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$144 - $295

Route

Depart

Return

Price

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 9/11

1 stop14h 36m

Chicago O'Hare Intl

Mon 9/23

1 stop16h 53m

$144

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 9/11

2 stops14h 06m

Chicago O'Hare Intl

Mon 9/23

1 stop16h 53m

$146

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/5

1 stop14h 36m

Chicago O'Hare Intl

Mon 9/9

1 stop16h 53m

$150

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/22

1 stop11h 34m

Chicago O'Hare Intl

Mon 8/26

1 stop15h 56m

$152

San Juan Luis Munoz Marin IntlChicago Midway

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 6/6

1 stop11h 16m

Chicago Midway

Mon 6/10

1 stop9h 38m

$197

San Juan Luis Munoz Marin IntlChicago Midway

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 6/5

1 stop7h 23m

Chicago Midway

Mon 6/10

1 stop17h 41m

$270

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 10/17

Nonstop5h 03m

Chicago O'Hare Intl

Mon 10/28

Nonstop4h 38m

$275

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/16

1 stop9h 12m

Chicago O'Hare Intl

Thu 10/24

1 stop8h 24m

$293

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/16

1 stop10h 17m

Chicago O'Hare Intl

Sun 8/18

1 stop6h 35m

$295

Flights are sorted by cheapest first

Deals found on 5/23

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

Best time to book a flight from Puerto Rico to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Puerto Rico 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 24, 2024.
Read reviews from past customers who have flown United Airlines, Spirit Airlines and American Airlines from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,997 reviews

Crew

8.7

Overall

8.2

Comfort

8.1

Boarding

8.3

Entertainment

7.8

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,997 reviews
Southwest
8.2
Very good
5,997 reviews

Crew

8.7

Overall

8.2

Comfort

8.1

Boarding

8.3

Entertainment

7.8

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

8.0
Very good
10,561 reviews
Southwest
8.2
Very good
5,997 reviews

Crew

8.7

Overall

8.2

Comfort

8.1

Boarding

8.3

Entertainment

7.8

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.6
Good
4,417 reviews
Southwest
8.2
Very good
5,997 reviews

Crew

8.7

Overall

8.2

Comfort

8.1

Boarding

8.3

Entertainment

7.8

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.4
Good
10,845 reviews
Southwest
8.2
Very good
5,997 reviews

Crew

8.7

Overall

8.2

Comfort

8.1

Boarding

8.3

Entertainment

7.8

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.3
Good
14,388 reviews
Southwest
8.2
Very good
5,997 reviews

Crew

8.7

Overall

8.2

Comfort

8.1

Boarding

8.3

Entertainment

7.8

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Related info for your journey

Find useful and relevant information for your journey from Puerto Rico to Chicago. 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 Puerto Rico to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Puerto Rico to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $144, but on average you can expect to pay $167.

  • Are there nonstop flights from Puerto Rico to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Puerto Rico to Chicago under $200. A good price for a nonstop flight from Puerto Rico to Chicago is less than $208.

  • Are there last-minute flights available from Puerto Rico to Chicago for under $300?

    There are currently 20+ open flights from Puerto Rico to Chicago within the next 7 days for less than $300.

  • What are the most popular routes from Puerto Rico to Chicago?

  • What are the most reliable airlines from Puerto Rico to Chicago?

    No one likes to see their flight delayed. When booking a flight from Puerto Rico to Chicago consider choosing United Airlines (78%), Air Canada (75%) or Air New Zealand (75%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from Puerto Rico to Chicago is $110. On average you can expect to pay $355. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $137.

  • What does SJU to ORD mean?

    SJU and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. SJU to ORD refers to a flight route from San Juan Luis Munoz Marin Intl Airport to Chicago O'Hare Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Puerto Rico to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Puerto Rico to Chicago 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 Puerto Rico to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Puerto Rico to Chicago 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 Puerto Rico to Chicago that include hotel bookings?

    Yes. In addition to deals on Puerto Rico to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Puerto Rico to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Chicago.

  • Can I find deals for business class flights from Puerto Rico to Chicago?

    Yes. Cheapflights offers flight deals from Puerto Rico to Chicago 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 Puerto Rico to Chicago that allow pets onboard?

    Many airlines flying from Puerto Rico to Chicago 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 Puerto Rico to Chicago?

    Yes, you can often find last-minute deals on Puerto Rico to Chicago 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 Puerto Rico to Chicago flight deals updated?

    The Puerto Rico to Chicago flight deals you see on this page were last updated on 5/23.

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

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

    Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $244). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $330). 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

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Top 6 airlines flying from Puerto Rico to Chicago

Discover the top 6 airlines that operate flights from Puerto Rico to Chicago. 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 2,725,499 searches. Data last updated May 24, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$113Average$269FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
FrontierCheapest$114Average$284FlexibilityNo cancel feeOn-time62%
Search Frontier flights
United AirlinesCheapest$147Average$473FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$156Average$448FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
JetBlueCheapest$168Average$351FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest$299Average$462FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Search flights from Puerto Rico to Chicago by cabin class

Find flights from Puerto Rico to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Puerto Rico to Chicago

Find hourly flight availability from Puerto Rico to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 24, 2024.
16%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
84%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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

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