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$67+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Jul 30 — Aug 61
From?
To?
Tue 7/30
Tue 8/6
1 adult, Economy
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How far in advance should I book a flight from Puerto Rico to Chicago?

To save up to 88% on this flight, we recommend booking at least 56 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 $256 1-2 weeks out and tickets from $296 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 $274 for the month, but tickets can be as low as $120. Due to multiple factors, prepare for potentially higher prices in March.

What is the cheapest time of day to fly from PR to 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 Puerto Rico to Chicago flights in July & August 2024

Find cheap flight options from Puerto Rico to Chicago specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 25, 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.
This eDestinos deal was found by Cheapflights users on 7/24. 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.
Tue 7/309:15 pmSJU - ORD
1 stop12h 59mSpirit Airlines
Sat 8/39:59 pmORD - SJU
1 stop17h 30mSpirit Airlines
Deal found 7/24$150
This eDestinos deal was found by Cheapflights users on 7/25. 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 8/239:31 amSJU - ORD
1 stop8h 57mFrontier
Sat 8/248:40 amORD - SJU
1 stop18h 41mFrontier
Deal found 7/25$152
This eDestinos deal was found by Cheapflights users on 7/25. 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 8/310:12 pmSJU - ORD
1 stop12h 02mSpirit Airlines
Sat 8/107:01 amORD - SJU
1 stop12h 48mSpirit Airlines
Deal found 7/25$155
This eDestinos deal was found by Cheapflights users on 7/25. 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.
Wed 8/143:03 amSJU - ORD
1 stop14h 48mFrontier
Wed 8/215:24 pmORD - SJU
1 stop7h 34mFrontier
Deal found 7/25$156
This eDestinos deal was found by Cheapflights users on 7/24. 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.
Tue 8/133:03 amSJU - ORD
1 stop22h 13mFrontier
Mon 8/266:13 pmORD - SJU
1 stop6h 45mFrontier
Deal found 7/24$161
This eDestinos deal was found by Cheapflights users on 7/25. 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.
Tue 7/309:15 pmSJU - ORD
1 stop12h 59mSpirit Airlines
Sat 8/310:26 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/25$163
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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.
Mon 7/298:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Tue 7/309:59 pmORD - SJU
1 stop14h 08mSpirit Airlines
Deal found 7/25$164
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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.
Fri 8/98:54 pmSJU - ORD
1 stop13h 20mSpirit Airlines
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Deal found 7/24$165
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/233:03 amSJU - MDW
1 stop14h 18mFrontier
Sat 8/315:16 pmMDW - SJU
1 stop10h 05mFrontier
Deal found 7/25$166

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 2,752,877 searches. Data last updated July 25, 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.
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/233:03 amSJU - MDW
1 stop14h 18mFrontier
Sat 8/315:16 pmMDW - SJU
1 stop10h 05mFrontier
Deal found 7/25$166
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/213:03 amSJU - MDW
1 stop7h 17mFrontier
Mon 8/262:13 pmMDW - SJU
1 stop13h 08mFrontier
Deal found 7/24$167
This Frontier deal was found by Cheapflights users on 7/25. 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.
Wed 8/213:03 amSJU - MDW
1 stop7h 17mFrontier
Mon 8/262:13 pmMDW - SJU
1 stop13h 08mFrontier
Deal found 7/25$168
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/266:30 amSJU - MDW
1 stop12h 28mFrontier
Mon 9/302:07 pmMDW - SJU
1 stop13h 08mFrontier
Deal found 7/24$170
This mytrip.com deal was found by Cheapflights users on 7/23. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/213:03 amSJU - MDW
1 stop7h 17mFrontier
Thu 8/291:24 pmMDW - SJU
1 stop9h 29mFrontier
Deal found 7/23$175
This Trip.com deal was found by Cheapflights users on 7/25. 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.
Fri 9/66:30 amSJU - MDW
1 stop8h 17mFrontier
Mon 9/98:03 pmMDW - SJU
1 stop13h 25mFrontier
Deal found 7/25$176
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/213:03 amSJU - MDW
1 stop7h 17mFrontier
Mon 8/2610:15 pmMDW - SJU
1 stop19h 48mFrontier
Deal found 7/24$177
This OneTravel deal was found by Cheapflights users on 7/25. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/248:49 pmBQN - MDW
1 stop13h 56mFrontier
Sat 8/3111:51 amMDW - BQN
1 stop6h 58mFrontier
Deal found 7/25$178
This Travelocity deal was found by Cheapflights users on 7/24. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/183:03 amSJU - MDW
1 stop11h 03mFrontier
Mon 8/267:14 pmMDW - SJU
1 stop12h 31mFrontier
Deal found 7/24$178

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 2,752,877 searches. Data last updated July 25, 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.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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.
Fri 8/24:20 pmSJU - ORD
Nonstop5h 13mSpirit Airlines
Tue 8/67:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Deal found 7/24$186
This Priceline deal was found by Cheapflights users on 7/24. 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.
Sat 8/38:54 pmSJU - ORD
1 stop13h 20mSpirit Airlines
Wed 8/76:16 pmORD - SJU
1 stop7h 03mSpirit Airlines
Deal found 7/24$187
This eDestinos deal was found by Cheapflights users on 7/25. 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.
Thu 8/19:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Sat 8/107:01 amORD - SJU
1 stop12h 48mSpirit Airlines
Deal found 7/25$188
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/38:54 pmSJU - ORD
1 stop13h 20mMultiple Airlines
Sat 8/102:02 pmORD - SJU
1 stop13h 19mMultiple Airlines
Deal found 7/24$190
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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.
Fri 8/212:37 amSJU - ORD
Nonstop5h 05mSpirit Airlines
Wed 8/76:16 pmORD - SJU
1 stop7h 03mSpirit Airlines
Deal found 7/25$192
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:37 amSJU - ORD
Nonstop5h 05mMultiple Airlines
Thu 8/87:12 pmORD - SJU
1 stop12h 14mMultiple Airlines
Deal found 7/24$194
This eDestinos deal was found by Cheapflights users on 7/25. 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.
Thu 8/17:30 amSJU - ORD
Nonstop5h 08mSpirit Airlines
Sat 8/1010:26 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/25$197
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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.
Fri 8/212:37 amSJU - ORD
Nonstop5h 05mSpirit Airlines
Sat 8/172:10 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 7/25$199
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/212:37 amSJU - ORD
Nonstop5h 05mSpirit Airlines
Wed 8/76:16 pmORD - SJU
1 stop7h 03mSpirit Airlines
Deal found 7/24$200

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 2,752,877 searches. Data last updated July 25, 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.
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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.
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$67
This eDestinos deal was found by Cheapflights users on 7/24. 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.
Wed 8/78:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 7/24$79
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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.
Fri 9/610:46 pmSJU - ORD
1 stop12h 12mSpirit Airlines
Deal found 7/24$81
This mytrip.com deal was found by Cheapflights users on 7/24. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/297:19 pmSJU - MDW
1 stop12h 52mFrontier
Deal found 7/24$82
This Cheapflightsfares deal was found by Cheapflights users on 7/25. 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.
Tue 7/308:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 7/25$82
This mytrip.com deal was found by Cheapflights users on 7/25. 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.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/196:30 amSJU - MDW
1 stop12h 28mFrontier
Deal found 7/25$83
This OneTravel deal was found by Cheapflights users on 7/24. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/309:15 pmSJU - ORD
1 stop12h 59mSpirit Airlines
Deal found 7/24$83
This Frontier deal was found by Cheapflights users on 7/25. 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.
Thu 9/266:30 amSJU - MDW
1 stop12h 28mFrontier
Deal found 7/25$84
This eDestinos deal was found by Cheapflights users on 7/24. 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.
Wed 7/318:15 pmSJU - ORD
1 stop13h 59mSpirit Airlines
Deal found 7/24$84

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 2,752,877 searches. Data last updated July 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$152 - $306

Route

Depart

Return

Price

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/23

1 stop8h 57m

Chicago O'Hare Intl

Sat 8/24

1 stop18h 41m

$152

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 9/6

1 stop12h 12m

Chicago O'Hare Intl

Sun 9/8

1 stop13h 56m

$154

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/14

1 stop14h 48m

Chicago O'Hare Intl

Wed 8/21

1 stop7h 34m

$156

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/13

1 stop22h 13m

Chicago O'Hare Intl

Mon 8/26

1 stop6h 45m

$161

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 8/7

1 stop13h 59m

Chicago O'Hare Intl

Mon 8/12

1 stop8h 06m

$163

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 8/13

1 stop13h 40m

Chicago O'Hare Intl

Thu 8/22

1 stop9h 57m

$175

Aguadilla BorinquenChicago O'Hare Intl

BQN - ORD

BQNORD

Aguadilla Borinquen

Fri 9/20

1 stop10h 18m

Chicago O'Hare Intl

Wed 10/2

1 stop9h 24m

$180

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 8/31

2 stops17h 14m

Chicago O'Hare Intl

Tue 9/3

1 stop19h 03m

$180

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 9/25

2 stops12h 25m

Chicago O'Hare Intl

Wed 10/2

2 stops9h 01m

$306

Flights are sorted by cheapest first

Deals found on 7/25

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 July 25, 2024.
Read reviews from past customers who have flown United Airlines, Spirit 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.
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

United Airlines
7.4
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

American Airlines
7.3
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Spirit Airlines
6.4
Okay
8,407 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Frontier
6.2
Okay
3,835 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

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 Frontier for just $152, but on average you can expect to pay $166.

  • 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 $218.

  • Are there last-minute flights available from Puerto Rico to Chicago for under $200?

    There are currently 20+ open flights from Puerto Rico to Chicago within the next 7 days for less than $200.

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

    $67 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $82 and $90, 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 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 $93. On average you can expect to pay $346. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $148.

  • 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 7/25.

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

    Consider American Airlines, JetBlue or Delta when booking your flight. These represent the most popular airlines when flying from Puerto Rico to Chicago.

  • What is the cheapest month 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 $245). 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.

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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
Santo Domingo to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Santo Domingo to Midway flights
Kingston to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
George Town to O'Hare Intl flights
Oranjestad to St. Louis flights
Montego Bay to Midway flights
Punta Cana to Midway flights
Aguadilla to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Port of Spain to St. Louis flights
Nassau to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Nassau to Midway flights
Roseau to O'Hare Intl flights
Simpson Bay to Midway flights
Port Au Prince to O'Hare Intl flights
Vieques to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
St. George's to St. Louis flights
Road Town to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Culebra to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
St. John's to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to Midway 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 2,752,877 searches. Data last updated July 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$104Average$276FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$110Average$248FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$162Average$457FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$168Average$310FlexibilityNo cancel feeOn-time62%
DeltaCheapest$172Average$484FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$289Average$478FlexibilityNo cancel feeOn-time71%
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Orlando to Miami flights
Jacksonville to Miami flights
New York to Punta Cana flights
Orlando Airport to San Juan flights
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San Francisco to Honolulu flights
Puerto Rico to Charlottesville 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.
First Class
Business Classfrom $436/person
Prem Econ Class
Economy Classfrom $75/person

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 July 25, 2024.
1%of flight departuresEarly morningMidnight to 6 am
11%of flight departuresMorning6 am to noon
88%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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