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Cheap flights from Puerto Rico to Chicago (CHI) from $46

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
SJU — CHI
May 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
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 85% on this flight, we recommend booking at least 16 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Puerto Rico to Chicago from $238 1-2 weeks out and tickets from $311 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 $270 for the month, but tickets can be as low as $122. Due to multiple factors, prepare for potentially higher prices in March.

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

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

Cheap Spirit Airlines flights from Puerto Rico to Chicago

Explore cheap flight options specifically provided by Spirit Airlines for the route between Puerto Rico and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Find some of the cheapest Spirit Airlines flights traveling from Puerto Rico to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Tue 9/1012:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Tue 9/2410:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Deal found 5/15$135
Wed 6/58:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Tue 6/257:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/15$145
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Tue 6/257:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/15$147
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/245:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/15$152
Tue 9/107:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Tue 9/249:25 pmORD - SJU
2 stops13h 03mSpirit Airlines
Deal found 5/15$160
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Sat 6/225:05 amORD - SJU
1 stop11h 47mSpirit Airlines
Deal found 5/15$162
Wed 5/2912:32 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Mon 6/39:25 pmORD - SJU
2 stops20h 46mSpirit Airlines
Deal found 5/15$165
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/225:05 amORD - SJU
1 stop11h 47mSpirit Airlines
Deal found 5/15$166
Wed 5/2912:32 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Deal found 5/15$168

Cheap United Airlines flights from Puerto Rico to Chicago

Explore cheap flight options specifically provided by United Airlines for the route between Puerto Rico and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Take a gander at the lowest prices we've found on United Airlines flights from Puerto Rico to Chicago. Check back soon if you're not seeing flights that suit your needs.
Fri 5/241:05 amSJU - ORD
1 stop10h 30mUnited Airlines
Tue 5/288:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/15$352
Wed 5/221:05 amSJU - ORD
1 stop9h 29mUnited Airlines
Mon 5/278:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/16$367
Fri 5/241:05 amSJU - ORD
1 stop7h 55mUnited Airlines
Sat 6/16:07 pmORD - SJU
Nonstop4h 47mUnited Airlines
Deal found 5/16$382
Wed 5/221:05 amSJU - ORD
1 stop9h 29mUnited Airlines
Mon 5/277:10 amORD - SJU
1 stop12h 28mUnited Airlines
Deal found 5/16$386
Thu 5/233:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Mon 5/278:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/16$431
Thu 5/233:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Wed 5/292:25 pmORD - SJU
1 stop8h 32mUnited Airlines
Deal found 5/15$437
Fri 5/243:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Mon 5/278:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/16$481
Thu 5/233:50 pmSJU - ORD
Nonstop5h 11mUnited Airlines
Wed 5/298:52 amORD - SJU
Nonstop4h 50mUnited Airlines
Deal found 5/16$488
Thu 6/2012:15 amBQN - ORD
1 stop9h 20mUnited Airlines
Wed 6/261:12 pmORD - BQN
1 stop8h 57mUnited Airlines
Deal found 5/15$599

Cheap Puerto Rico to Chicago flights in May & June 2024

Find cheap flight options from Puerto Rico to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 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.
Wed 6/58:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Tue 6/257:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/15$145
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Tue 6/257:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/15$147
Tue 5/2812:22 pmSJU - ORD
2 stops29h 13mMultiple Airlines
Wed 5/299:15 pmORD - SJU
1 stop27h 00mMultiple Airlines
Deal found 5/15$153
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Sat 6/225:05 amORD - SJU
1 stop11h 47mSpirit Airlines
Deal found 5/15$162
Wed 5/2912:32 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Mon 6/39:25 pmORD - SJU
2 stops20h 46mSpirit Airlines
Deal found 5/15$165
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/225:05 amORD - SJU
1 stop11h 47mSpirit Airlines
Deal found 5/15$166
Wed 5/2912:32 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Mon 6/35:25 pmORD - SJU
1 stop24h 32mSpirit Airlines
Deal found 5/15$168
Tue 6/412:32 pmSJU - ORD
1 stop20h 49mSpirit Airlines
Fri 6/79:10 pmORD - SJU
1 stop29h 00mSpirit Airlines
Deal found 5/15$170
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Mon 6/245:34 pmORD - SJU
1 stop19h 33mSpirit Airlines
Deal found 5/15$172

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 2,637,452 searches. Data last updated May 16, 2024.
Scroll through some of the best deals on flights from Puerto Rico to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Tue 9/1012:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Tue 9/2410:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Deal found 5/15$135
Wed 6/58:06 pmSJU - ORD
1 stop14h 55mSpirit Airlines
Tue 6/257:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/15$145
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Tue 6/257:36 amORD - SJU
1 stop10h 29mSpirit Airlines
Deal found 5/15$147
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/245:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Deal found 5/15$152
Tue 5/2812:22 pmSJU - ORD
2 stops29h 13mMultiple Airlines
Wed 5/299:15 pmORD - SJU
1 stop27h 00mMultiple Airlines
Deal found 5/15$153
Tue 9/107:57 pmSJU - ORD
1 stop14h 36mSpirit Airlines
Tue 9/249:25 pmORD - SJU
2 stops13h 03mSpirit Airlines
Deal found 5/15$160
Tue 8/208:02 pmSJU - ORD
1 stop14h 31mSpirit Airlines
Mon 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/15$162
Wed 5/2912:32 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Mon 6/39:25 pmORD - SJU
2 stops20h 46mSpirit Airlines
Deal found 5/15$165
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/225:05 amORD - SJU
1 stop11h 47mSpirit Airlines
Deal found 5/15$166

Non-stop flights to Chicago from Puerto Rico

Discover non-stop flight options from Puerto Rico to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Take a look at some of the direct flights traveling from Puerto Rico to Chicago in the near future. Users can also choose from other Puerto Rico to Chicago flights by using the search form above.
Tue 9/106:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/2411:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/15$177
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/155:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 5/15$181
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/85:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 5/15$182
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Wed 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/15$194
Thu 9/126:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Tue 9/1711:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/15$195
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Sat 6/225:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Deal found 5/15$197
Tue 10/16:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Thu 10/311:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Deal found 5/15$198
Thu 6/64:09 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Mon 6/1010:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Deal found 5/15$204
Tue 6/46:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Mon 6/249:15 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/15$209

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 2,637,452 searches. Data last updated May 16, 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.
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mSpirit Airlines
Tue 5/2811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Deal found 5/15$189
Fri 5/246:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Tue 5/2811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Deal found 5/15$197
Fri 5/246:10 amSJU - ORD
Nonstop5h 10mSpirit Airlines
Tue 5/286:40 pmORD - SJU
1 stop15h 52mSpirit Airlines
Deal found 5/14$199
Fri 5/249:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Tue 5/2811:10 amORD - SJU
Nonstop4h 53mSpirit Airlines
Deal found 5/15$207
Fri 5/249:00 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Tue 5/286:40 pmORD - SJU
1 stop15h 52mSpirit Airlines
Deal found 5/14$209
Wed 5/2212:59 amSJU - ORD
1 stop10h 54mMultiple Airlines
Thu 5/309:03 amORD - SJU
1 stop8h 54mMultiple Airlines
Deal found 5/16$212
Sat 5/2512:32 pmSJU - ORD
1 stop9h 00mSpirit Airlines
Mon 6/39:25 pmORD - SJU
1 stop14h 16mSpirit Airlines
Deal found 5/15$215
Thu 5/236:10 amSJU - ORD
Nonstop5h 10mMultiple Airlines
Wed 5/299:15 pmORD - SJU
1 stop10h 29mMultiple Airlines
Deal found 5/15$216
Thu 5/239:28 amSJU - ORD
1 stop16h 40mMultiple Airlines
Thu 5/3010:03 amORD - SJU
1 stop7h 54mMultiple Airlines
Deal found 5/16$220

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 2,637,452 searches. Data last updated May 16, 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.
Mon 6/39:07 pmSJU - ORD
1 stop13h 48mSpirit Airlines
Deal found 5/15$46
Tue 5/2812:32 pmSJU - ORD
1 stop10h 24mSpirit Airlines
Deal found 5/16$47
Tue 9/1712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/14$64
Wed 6/59:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/15$65
Wed 6/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/15$69
Wed 8/2112:28 pmSJU - ORD
1 stop7h 29mSpirit Airlines
Deal found 5/15$72
Tue 8/2012:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/15$76
Wed 5/2912:32 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Deal found 5/15$77
Thu 6/69:15 pmSJU - ORD
1 stop12h 49mSpirit Airlines
Deal found 5/15$79

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 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$135 - $394

Route

Depart

Return

Price

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 9/10

1 stop10h 28m

Chicago O'Hare Intl

Tue 9/24

1 stop7h 38m

$135

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 6/5

1 stop14h 55m

Chicago O'Hare Intl

Tue 6/25

1 stop10h 29m

$145

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 6/4

Nonstop5h 10m

Chicago O'Hare Intl

Tue 6/25

1 stop10h 29m

$147

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 9/10

Nonstop5h 14m

Chicago O'Hare Intl

Tue 9/24

1 stop16h 53m

$152

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 5/28

2 stops29h 13m

Chicago O'Hare Intl

Wed 5/29

1 stop27h 00m

$153

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 5/28

2 stops29h 13m

Chicago O'Hare Intl

Sat 6/1

1 stop8h 40m

$177

San Juan Luis Munoz Marin IntlChicago O'Hare Intl

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 6/5

1 stop13h 55m

Chicago O'Hare Intl

Sat 6/22

2 stops15h 40m

$180

San Juan Luis Munoz Marin IntlChicago Midway

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mon 6/3

1 stop9h 53m

Chicago Midway

Mon 6/10

1 stop17h 41m

$213

San Juan Luis Munoz Marin IntlChicago Midway

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Tue 10/22

1 stop9h 50m

Chicago Midway

Sat 10/26

1 stop6h 58m

$394

Flights are sorted by cheapest first

Deals found on 5/15

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 16, 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.
Delta
8.0
Very good
10,673 reviews
Check prices

Food

7.4

Comfort

7.9

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Food

7.4

Comfort

7.9

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

JetBlue
7.6
Good
4,472 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Food

7.4

Comfort

7.9

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
10,924 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Food

7.4

Comfort

7.9

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

American Airlines
7.3
Good
14,514 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Food

7.4

Comfort

7.9

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Spirit Airlines
6.4
Okay
8,672 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Food

7.4

Comfort

7.9

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

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

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

    Yes, there are multiple flights from Puerto Rico to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $135, but on average you can expect to pay $165.

  • 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 $213.

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

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

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

    The cheapest flight price from Puerto Rico to Chicago is $109. On average you can expect to pay $374. The most popular route, (San Juan Luis Munoz Marin Intl - Chicago O'Hare Intl), can usually be booked for $122.

  • What does SJU to ORD mean?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    The Puerto Rico to Chicago flight deals you see on this page were last updated on 5/15.

See more FAQs

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Alternative routes for Puerto Rico to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Luis Munoz Marin Intl to St. Louis flights
Montego Bay to O'Hare Intl flights
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Nassau to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Punta Cana to Midway flights
Montego Bay to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Nassau to Midway flights
Port of Spain to St. Louis flights
Nassau to St. Louis flights
Saint Thomas Island to St. Louis flights
Christiansted to O'Hare Intl flights
Oranjestad to St. Louis flights
St. George's to St. Louis flights
Aguadilla to Midway flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Simpson Bay to Midway flights
Vieques to O'Hare Intl flights
Port Au Prince 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 2,637,452 searches. Data last updated May 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$202FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$114Average$269FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
United AirlinesCheapest$148Average$483FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$156Average$448FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
JetBlueCheapest$168Average$351FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
American AirlinesCheapest$299Average$462FlexibilityNo cancel feeOn-time71%
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Fort Lauderdale to New York flights
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New York to Guyana flights
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Orlando to Miami flights
Jacksonville to Miami flights
New York to Punta Cana flights
Orlando Airport to San Juan flights
Los Angeles to Beijing flights
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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 $488/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 May 16, 2024.
11%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
89%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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Fly with Cheapflights

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

How does Cheapflights help users find flights from Puerto Rico to Chicago?

Deals for Puerto Rico to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Puerto Rico to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Puerto Rico to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Puerto Rico to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Puerto Rico to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Puerto Rico today and book when prices fit your budget.

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