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$68+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
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 December 22, 2024.

Round-trip from

$151
(FlightHub)

One-way from

$68
(FlightHub)
From Puerto Rico to Chicago (CHI)
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One-way flight from Puerto Rico to Chicago (CHI)
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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 December 22, 2024.

This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/279:00 pmSJU - ORD
1 stop14h 54mFrontier
Sat 1/410:49 amORD - SJU
1 stop14h 00mFrontier
Deal found 12/20$244
This Booking.com deal was found by Cheapflights users on 12/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:13 pmSJU - ORD
1 stop19h 33mMultiple Airlines
Sun 1/51:00 pmORD - SJU
Nonstop4h 36mMultiple Airlines
Deal found 12/21$265
This eDestinos deal was found by Cheapflights users on 12/21. 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.
Sat 12/285:10 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Tue 1/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 12/21$268
This Frontier deal was found by Cheapflights users on 12/21. 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 12/318:10 pmSJU - MDW
1 stop14h 11mFrontier
Sat 1/47:35 amMDW - SJU
1 stop11h 35mFrontier
Deal found 12/21$279
This Trip.com deal was found by Cheapflights users on 12/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:45 amSJU - MDW
1 stop12h 39mMultiple Airlines
Sat 1/47:35 amMDW - SJU
1 stop11h 35mMultiple Airlines
Deal found 12/20$403
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:05 amSJU - ORD
2 stops11h 04mAmerican Airlines
Wed 1/112:15 pmORD - SJU
1 stop8h 55mAmerican Airlines
Deal found 12/21$424
This Delta deal was found by Cheapflights users on 12/21. 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.
Fri 12/276:30 amSJU - MDW
1 stop6h 51mDelta
Sun 1/56:00 amMDW - SJU
1 stop9h 15mDelta
Deal found 12/21$484
This Southwest deal was found by Cheapflights users on 12/21. 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.
Fri 12/274:55 pmSJU - MDW
1 stop8h 40mSouthwest
Sun 1/512:10 pmMDW - SJU
2 stops10h 30mSouthwest
Deal found 12/21$499
This deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:50 pmSJU - ORD
1 stop7h 35mUnited Airlines
Wed 1/12:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Deal found 12/21$510
This Southwest deal was found by Cheapflights users on 12/21. 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.
Tue 12/2411:45 amSJU - ORD
2 stops11h 45mSouthwest
Fri 1/311:25 amORD - SJU
2 stops11h 15mSouthwest
Deal found 12/21$518

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 2,558,603 searches. Data last updated December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 2/24

10:43 pm-3:12 pm

1 stop18h 29m

Chicago Midway

Fri 2/28

2:41 pm-1:11 am

1 stop8h 30m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/16

9:26 pm-12:51 am

Nonstop5h 25m

Chicago O'Hare Intl

Tue 1/21

1:44 pm-8:21 pm

Nonstop4h 37m

$151

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sun 2/23

3:54 am-4:03 pm

1 stop14h 09m

Chicago O'Hare Intl

Fri 2/28

7:18 pm-9:35 am

1 stop12h 17m

$152

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/20

7:57 pm-11:20 pm

Nonstop5h 23m

Chicago O'Hare Intl

Mon 2/24

7:08 pm-9:35 am

1 stop12h 27m

$153

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/23

6:55 pm-2:19 pm

1 stop21h 24m

Chicago Midway

Mon 1/27

7:45 am-1:59 am

1 stop16h 14m

$209

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/2

3:05 pm-7:25 pm

Nonstop5h 20m

Chicago O'Hare Intl

Mon 5/5

8:05 am-1:45 pm

Nonstop4h 40m

$230

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 1/29

2:55 pm-7:45 pm

1 stop6h 50m

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

$304

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/24

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

Tue 1/28

12:44 pm-11:46 pm

1 stop9h 02m

$324

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/23

2:05 am-10:44 am

1 stop10h 39m

Chicago O'Hare Intl

Sun 1/26

8:50 am-9:28 pm

1 stop10h 38m

$324

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 1/28

4:15 pm-10:20 pm

1 stop8h 05m

Chicago O'Hare Intl

Sat 2/1

6:30 am-10:50 pm

2 stops14h 20m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 29 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, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $245). Flying from Puerto Rico to Chicago in March is currently the most expensive (average of $317). 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 December 22, 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 December 22, 2024.

The most flights from PR0 to CHI are scheduled on a Saturday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 December 22, 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
4,804 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,597 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,035 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,804 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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?

    $68 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 Southwest, with prices starting from $70 and $117, 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 Aguadilla Borinquen - 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 American Airlines (90%), Alaska Airlines (90%) or Spirit Airlines (88%) 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 $65. On average you can expect to pay $416. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $126.

  • 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, August is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $245). Flying from Puerto Rico to Chicago in March is currently the most expensive (average of $317). 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.

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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
Luis Munoz Marin Intl to St. Louis flights
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Nassau to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Santo Domingo to Midway flights
Nassau to Midway flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Kingston to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
George Town to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Montego Bay to Midway flights
Aguadilla to O'Hare Intl flights
Port of Spain to St. Louis flights
Simpson Bay to O'Hare Intl flights
Aguadilla to Midway flights
Bridgetown to O'Hare Intl flights
St. John's to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Port Au Prince to Midway flights
Saint Thomas Island to St. Louis flights
Nassau to St. Louis flights
St. George's to St. Louis flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Simpson Bay to Midway flights
Culebra to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl flights
Road Town 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 2,558,603 searches. Data last updated December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$373FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$256FlexibilityNo cancel feeOn-time65%
DeltaCheapest$187Average$453FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$210Average$484FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$306Average$464FlexibilityNo cancel feeOn-time71%
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