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$82+ Cheap flights from Chicago (CHI) to Puerto Rico

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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jul 30 — Aug 61
From?
To?
Tue 7/30
1 adult, Economy
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How far in advance should I book a flight from Chicago to Puerto Rico?

Find a great deal and save up to 11% by booking at least 32 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Puerto Rico within the next two weeks, with the cheapest ticket starting at $256.

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

January is one of the best times of the year to fly to Puerto Rico from Chicago. Prices for January average $328 per person but you can even find prices for as low as $110. The most expensive prices can be found in the month of March. Opting for a January flight can save you 55% on your journey compared to booking in March

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

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

Cheap Chicago to Puerto Rico flights in July & August 2024

Find cheap flight options from Chicago to Puerto Rico 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 Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
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.
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Wed 8/2110:46 amSJU - ORD
1 stop10h 22mSpirit Airlines
Deal found 7/24$140
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:06 pmORD - SJU
1 stop6h 30mSpirit Airlines
Sat 8/1012:18 pmSJU - ORD
1 stop8h 41mSpirit Airlines
Deal found 7/24$143
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 8/67:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$148
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 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$149
This FareScan 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Wed 8/146:00 amSJU - ORD
2 stops18h 17mSpirit Airlines
Deal found 7/24$152
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.
Mon 8/57:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$153
This FareScan 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/69:15 pmORD - SJU
1 stop20h 53mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$155
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.
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Tue 8/208:50 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 7/24$156
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/137:32 amORD - SJU
1 stop10h 36mMultiple Airlines
Mon 8/193:03 amSJU - ORD
1 stop20h 25mMultiple Airlines
Deal found 7/24$157

Chicago to Puerto Rico 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Puerto Rico in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
Scroll through some of the best deals on flights from Chicago to Puerto Rico in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
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.
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Wed 8/2110:46 amSJU - ORD
1 stop10h 22mSpirit Airlines
Deal found 7/24$140
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:06 pmORD - SJU
1 stop6h 30mSpirit Airlines
Sat 8/1012:18 pmSJU - ORD
1 stop8h 41mSpirit Airlines
Deal found 7/24$143
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 8/67:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$148
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 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$149
This FareScan 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Wed 8/146:00 amSJU - ORD
2 stops18h 17mSpirit Airlines
Deal found 7/24$152
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.
Mon 8/57:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$153
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.
Fri 9/137:00 amORD - SJU
1 stop13h 56mSpirit Airlines
Mon 9/1610:46 pmSJU - ORD
1 stop12h 12mSpirit Airlines
Deal found 7/24$154
This FareScan 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/69:15 pmORD - SJU
1 stop20h 53mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$155
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.
Tue 8/137:32 amORD - SJU
1 stop10h 36mSpirit Airlines
Tue 8/208:50 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 7/24$156

Chicago to Puerto Rico flights leaving soon

Find last-minute flight options from Chicago to Puerto Rico for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
Book one of these great deals on flights from Chicago to Puerto Rico. It's wise to confirm all flight details are correct before booking.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/37:06 pmORD - SJU
1 stop6h 30mSpirit Airlines
Sat 8/1012:18 pmSJU - ORD
1 stop8h 41mSpirit Airlines
Deal found 7/24$143
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 8/67:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$148
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 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$149
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.
Mon 8/57:01 amORD - SJU
1 stop11h 33mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$153
This FareScan 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/69:15 pmORD - SJU
1 stop20h 53mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$155
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.
Tue 8/69:15 pmORD - SJU
1 stop14h 16mSpirit Airlines
Tue 8/208:50 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 7/24$157
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.
Mon 7/299:59 pmORD - SJU
1 stop13h 32mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$158
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.
Thu 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/25$159
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.
Thu 8/15:42 pmORD - SJU
1 stop7h 12mSpirit Airlines
Thu 8/89:15 pmSJU - ORD
1 stop12h 48mSpirit Airlines
Deal found 7/24$160

One-way flights to Puerto Rico from Chicago

Search for one-way flight options from Chicago to Puerto Rico. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
Take a look at some of the one-way flights we've detected from Chicago to Puerto Rico. Users can also find round-trip Chicago to Puerto Rico flights by using the search form above.
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 9/266:53 pmMDW - SJU
1 stop8h 22mFrontier
Deal found 7/24$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 8/225:24 pmORD - SJU
1 stop9h 57mFrontier
Deal found 7/25$84
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.
Sat 8/2411:51 amMDW - SJU
1 stop13h 07mFrontier
Deal found 7/25$84
This FareScan 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/275:22 pmORD - SJU
2 stops29h 50mSpirit Airlines
Deal found 7/24$85
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 8/73:32 pmMDW - SJU
1 stop9h 22mFrontier
Deal found 7/24$85
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 8/87:12 pmORD - SJU
1 stop12h 14mFrontier
Deal found 7/25$86
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/76:16 pmORD - SJU
1 stop7h 03mSpirit Airlines
Deal found 7/24$87
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.
Sat 9/286:48 pmORD - BQN
1 stop23h 15mFrontier
Deal found 7/25$87
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 8/89:04 pmMDW - SJU
1 stop10h 22mFrontier
Deal found 7/24$87

Find flights from Chicago to Puerto Rico within your budget

Customize your flight search to find flights from Chicago to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$140 - $324

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/13

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Wed 8/21

1 stop10h 22m

$140

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/6

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Thu 8/8

1 stop12h 48m

$148

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/13

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Wed 8/14

2 stops18h 17m

$152

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 8/10

1 stop13h 19m

San Juan Luis Munoz Marin Intl

Mon 8/19

1 stop20h 25m

$156

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/13

1 stop10h 36m

San Juan Luis Munoz Marin Intl

Mon 8/19

1 stop20h 25m

$157

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/6

1 stop14h 16m

San Juan Luis Munoz Marin Intl

Mon 8/19

1 stop20h 25m

$158

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 8/23

1 stop20h 51m

San Juan Luis Munoz Marin Intl

Fri 8/30

1 stop7h 38m

$161

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/3

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

Tue 12/10

1 stop10h 48m

$281

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 12/7

1 stop6h 58m

San Juan Luis Munoz Marin Intl

Wed 12/11

1 stop11h 44m

$324

Flights are sorted by cheapest first

Deals found on 7/24

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

Best time to book a flight from Chicago to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated July 25, 2024.
Read through reviews of airlines operating flights from Chicago to Puerto Rico, such as Spirit Airlines, Frontier and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

Comfort

7.9

Overall

8.0

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

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

Comfort

7.9

Overall

8.0

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

JetBlue
7.6
Good
3,996 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

Comfort

7.9

Overall

8.0

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

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

Comfort

7.9

Overall

8.0

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

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

Comfort

7.9

Overall

8.0

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

Boarding

8.2

Crew

8.6

Entertainment

8.0

Food

7.4

Comfort

7.9

Overall

8.0

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 Chicago to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago to Puerto Rico for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Puerto Rico for under $200. The cheapest flight booked recently is on Spirit Airlines for just $140, but on average you can expect to pay $158.

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

    Cheapflights has at least 20 direct flights from Chicago to Puerto Rico under $200. A good price for a nonstop flight from Chicago to Puerto Rico is less than $210.

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

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

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $82. Spirit Airlines flights start at $85 while deals on United Airlines start at $90 one-way.

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

    The most popular flight routes from Chicago to Puerto Rico are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl and Chicago O'Hare Intl - Aguadilla Borinquen.

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

    Before booking your flight to Puerto Rico from Chicago, check out the most reliable airlines to get you to your destination on time: Air Canada (85%), United Airlines (85%), Air New Zealand( 85%).

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

    On average you can expect to pay $753 for a flight from Chicago to Puerto Rico. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) is currently priced at $143.

  • What does ORD to SJU mean?

    Chicago O'Hare Intl Airport is ORD and San Juan Luis Munoz Marin Intl Airport is SJU. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Ready for more IATA code knowledge? These are related airports for your current travel destination: Aguadilla Borinquen Airport (BQN), Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Culebra Airport (CPX), Vieques Airport (VQS).

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

    The amount of baggage you can bring on your Chicago to Puerto Rico flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Puerto Rico with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Puerto Rico flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Puerto Rico that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Puerto Rico that allow pets onboard?

    Many airlines flying from Chicago to Puerto Rico offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Puerto Rico?

    Yes, you can often find last-minute deals on Chicago to Puerto Rico flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Puerto Rico flight deals updated?

    The Chicago to Puerto Rico flight deals you see on this page were last updated on 7/24.

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

    When booking a flight from Chicago to Puerto Rico, you may want to consider flying on American Airlines, Alaska Airlines or JetBlue as they are the most popular for this route.

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

    Currently, September is the cheapest month in which you can book a flight from Chicago to Puerto Rico (average of $245). Flying from Chicago to Puerto Rico in March is currently the most expensive (average of $336). 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 Chicago to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to George Town flights
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Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
Midway to Oranjestad flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
Midway to Nassau flights
O'Hare Intl to Castries flights
St. Louis to Montego Bay flights
St. Louis to Punta Cana flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
St. Louis to Oranjestad flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Kingston flights
Midway to Simpson Bay flights
O'Hare Intl to Christiansted flights
St. Louis to Providenciales flights
Midway to George Town flights
Midway to Santo Domingo flights
Midway to Providenciales flights
O'Hare Intl to St. John's flights
St. Louis to George Town flights
O'Hare Intl to Santiago de los Caballeros flights
Moline to Luis Munoz Marin Intl flights
St. Louis to St. John's flights
Midway to Castries flights
O'Hare Intl to Port of Spain flights
St. Louis to Willemstad flights
St. Louis to Nassau flights
O'Hare Intl to Kralendijk flights
St. Louis to Bridgetown flights
O'Hare Intl to St. George's flights
Midway to Kingston flights
St. Louis to Santo Domingo flights
St. Louis to Christiansted flights
Evansville to Luis Munoz Marin Intl flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Georgetown flights

Top 7 airlines flying from Chicago to Puerto Rico

Discover the top 7 airlines that operate flights from Chicago to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$93Average$278FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$134Average$303FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$137Average$439FlexibilityNo cancel feeOn-time62%
DeltaCheapest$150Average$578FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$185Average$489FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$321Average$493FlexibilityNo cancel feeOn-time71%
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Search flights from Chicago to Puerto Rico by cabin class

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

Find hourly flight availability from Chicago to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 25, 2024.
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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