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$64+ Cheap flights from Puerto Rico to Chicago (CHI)

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Puerto Rico to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Puerto Rico (PR0) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

Find flight deals from Puerto Rico to Chicago

Cheapest flights from Puerto Rico to Chicago
Explore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Priceline deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:55 pmSJU - MDW
1 stop12h 25mFrontier
Mon 12/97:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/20$158
This Cheapflightsfares deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/184:43 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Thu 1/21:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 11/20$158
This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/223:43 amBQN - ORD
1 stop8h 11mFrontier
Thu 1/2310:33 amORD - BQN
1 stop14h 13mFrontier
Deal found 11/19$160
This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/62:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Mon 12/94:58 pmORD - SJU
1 stop7h 04mMultiple Airlines
Deal found 11/20$161
This Frontier deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2410:01 pmSJU - ORD
1 stop13h 23mFrontier
Thu 1/22:19 pmORD - SJU
1 stop8h 22mFrontier
Deal found 11/20$168
This United Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/68:35 amSJU - ORD
Nonstop5h 19mUnited Airlines
Mon 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Deal found 11/20$221
This eDestinos deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/65:25 amSJU - MDW
2 stops17h 37mMultiple Airlines
Mon 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Deal found 11/20$238
This Southwest deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:10 amSJU - MDW
1 stop10h 05mSouthwest
Mon 12/1611:55 amMDW - SJU
2 stops10h 50mSouthwest
Deal found 11/20$312
This eDestinos deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/223:43 amBQN - ORD
2 stops38h 45mMultiple Airlines
Thu 1/235:05 amORD - BQN
3 stops43h 41mMultiple Airlines
Deal found 11/19$315
This eDestinos deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/223:43 amBQN - MDW
2 stops37h 28mFrontier
Thu 1/234:08 pmMDW - BQN
2 stops32h 38mFrontier
Deal found 11/19$323
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:30 amSJU - MDW
1 stop10h 45mDelta
Tue 12/106:00 amMDW - SJU
1 stop9h 15mDelta
Deal found 11/20$404
This United Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/221:09 amBQN - ORD
1 stop8h 35mUnited Airlines
Thu 1/236:14 pmORD - BQN
2 stops27h 43mUnited Airlines
Deal found 11/20$476

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/6

1:55 pm-12:20 am

1 stop12h 25m

Chicago Midway

Mon 12/9

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 12/18

4:43 pm-8:13 pm

Nonstop5h 30m

Chicago O'Hare Intl

Thu 1/2

1:00 pm-7:36 pm

Nonstop4h 36m

$158

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Sun 12/22

3:43 am-9:54 am

1 stop8h 11m

Chicago O'Hare Intl

Thu 1/23

10:33 am-2:46 am

1 stop14h 13m

$160

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/6

2:17 pm-5:47 pm

Nonstop5h 30m

Chicago O'Hare Intl

Mon 12/9

4:58 pm-2:02 am

1 stop7h 04m

$161

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 12/24

10:01 pm-9:24 am

1 stop13h 23m

Chicago O'Hare Intl

Thu 1/2

2:19 pm-12:41 am

1 stop8h 22m

$168

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

Mon 1/27

6:15 am-3:19 pm

2 stops31h 04m

$200

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/6

8:35 am-11:54 am

Nonstop5h 19m

Chicago O'Hare Intl

Mon 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

$221

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 12/12

6:10 am-2:15 pm

1 stop10h 05m

Chicago Midway

Mon 12/16

11:55 am-12:45 am

2 stops10h 50m

$312

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

Sun 12/22

3:43 am-4:28 pm

2 stops38h 45m

Chicago O'Hare Intl

Thu 1/23

5:05 am-2:46 am

3 stops43h 41m

$315

AguadillaChicago

BQN - MDW

BQNMDW

Aguadilla Borinquen

Sun 12/22

3:43 am-3:11 pm

2 stops37h 28m

Chicago Midway

Thu 1/23

4:08 pm-2:46 am

2 stops32h 38m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 27 results
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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.

Travel insights for flights from Puerto Rico to Chicago

Get recent, data-driven insights about flights from Puerto Rico to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Puerto Rico to Chicago?

Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $232). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $308). 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.

What is the cheapest time of day to fly from PR to CHI?

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 November 21, 2024.

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.

Weekly flight availability from Puerto Rico to Chicago

Explore weekly flight availability from Puerto Rico to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 21, 2024.

The most flights from PR0 to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 November 21, 2024.
Read reviews from past customers who have flown Spirit Airlines, United Airlines and Frontier from Puerto Rico to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,759 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,395 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,173 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • What are the cheapest airlines to fly from Puerto Rico to Chicago one-way?

    $64 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $85 and $101, respectively.

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

    The most popular route from Puerto Rico to Chicago is San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl. You may also consider San Juan Luis Munoz Marin Intl - Chicago Midway or Mayagüez Eugenio M De Hostos - Chicago O'Hare Intl.

  • 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 Air Canada (84%), United Airlines (84%) or Air New Zealand (84%) 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 $95. On average you can expect to pay $736. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $129.

  • 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.

  • What is the cheapest month to book a flight from Puerto Rico to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $232). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $308). 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 Puerto Rico to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
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Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
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Nassau to Midway flights
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Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
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George Town to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to Midway flights
Saint Thomas Island to St. Louis flights
Willemstad to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Road Town to O'Hare Intl flights
Port of Spain to St. Louis flights
Nassau to St. Louis flights
St. John's to O'Hare Intl flights
St. George's to St. Louis flights
Aguadilla to Midway flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights

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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$287FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$453FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$202Average$483FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$379FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$303Average$473FlexibilityNo cancel feeOn-time71%
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