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Cheap flights from Chicago (CHI) to San Juan 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 8/27. 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.
CHI — SJU
Jun 4 — Jun 111
From?
To?
Tue 6/4
Tue 6/11
1 adult, Economy
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The best prices from Chicago to San Juan are usually found in October or August, booked 56 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from Chicago to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 30, 2024.

Popular in

March

Cheapest in

October

Round-trip from

$247

One-way from

$70
High demand for flights, 38% potential price rise
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Best time to find cheap flights, 24% potential price drop
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From Chicago (CHI) to San Juan
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One-way flight from Chicago (CHI) to San Juan
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What is the cheapest day to fly round-trip from Chicago to San Juan?

Saturday flights are found to be more expensive to fly from Chicago to San Juan. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to San Juan.

How far in advance should I book a flight from Chicago to San Juan?

Travelers have found it’s best to book a flight 57 days in advance to save up to 25% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 57 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to San Juan 1-2 weeks in advance for as low as $258, or $283 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to San Juan?

The best pricing can be found in the month of October. Prices to San Juan from Chicago average $319. You can even find prices in October for less than $319, as users have found deals to San Juan from as low as $90. The month of March appears to be one of the more expensive times to travel to San Juan from Chicago. Flying in the targeted month can save you up to 60%.

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

It’s typically best to fly out from Chicago to San Juan in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying in the evening, which is usually more expensive.

Cheap Spirit Airlines flights from Chicago to San Juan

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and San Juan. 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 2,784,634 searches. Data last updated May 30, 2024.
Peruse some of the lowest-priced Spirit Airlines flights we've found from Chicago to San Juan. It's recommended that users confirm their flight details before booking.
Tue 8/205:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/30$113
Tue 8/2010:33 amORD - SJU
1 stop7h 36mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/30$116
Tue 8/2010:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Tue 8/2712:28 pmSJU - ORD
1 stop10h 28mSpirit Airlines
Deal found 5/30$120
Tue 9/107:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Tue 9/247:57 pmSJU - ORD
1 stop29h 03mSpirit Airlines
Deal found 5/29$121
Tue 8/277:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Tue 8/271:00 amSJU - ORD
2 stops17h 27mSpirit Airlines
Deal found 5/29$122
Tue 8/2710:33 amORD - SJU
1 stop7h 38mSpirit Airlines
Wed 8/286:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$123
Mon 9/96:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Wed 9/117:57 pmSJU - ORD
1 stop22h 30mSpirit Airlines
Deal found 5/29$124
Mon 9/95:35 pmORD - SJU
1 stop16h 53mSpirit Airlines
Wed 9/116:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$125
Tue 8/277:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Wed 8/2812:28 pmSJU - ORD
1 stop7h 29mSpirit Airlines
Deal found 5/29$127

Cheap Frontier flights from Chicago to San Juan

Explore cheap flight options specifically provided by Frontier for the route between Chicago and San Juan. 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 2,784,634 searches. Data last updated May 30, 2024.
Some of the best deals we've found on Frontier flights traveling from Chicago to San Juan. Deals are refreshing constantly so come back soon for more options.
Sat 6/89:31 amMDW - SJU
1 stop16h 37mFrontier
Wed 6/129:36 pmSJU - MDW
1 stop9h 24mFrontier
Deal found 5/30$195
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Wed 6/1210:15 pmSJU - MDW
2 stops22h 41mFrontier
Deal found 5/30$201
Fri 6/75:58 pmORD - SJU
1 stop15h 45mFrontier
Tue 6/113:08 amSJU - ORD
1 stop23h 00mFrontier
Deal found 5/30$213
Wed 6/58:27 amMDW - SJU
1 stop17h 41mFrontier
Wed 6/126:00 amSJU - MDW
1 stop8h 32mFrontier
Deal found 5/30$225
Sat 6/89:31 amMDW - SJU
1 stop16h 37mFrontier
Wed 6/1210:15 pmSJU - MDW
2 stops22h 41mFrontier
Deal found 5/30$231
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Wed 6/123:08 amSJU - MDW
1 stop7h 23mFrontier
Deal found 5/30$236
Thu 6/62:36 pmMDW - SJU
1 stop16h 33mFrontier
Sat 6/85:57 pmSJU - MDW
1 stop16h 34mFrontier
Deal found 5/29$241
Tue 6/117:36 pmMDW - SJU
1 stop11h 33mFrontier
Thu 6/139:30 amSJU - MDW
2 stops11h 26mFrontier
Deal found 5/30$244
Fri 6/75:58 pmORD - SJU
1 stop15h 45mFrontier
Tue 6/113:08 amSJU - ORD
1 stop23h 00mFrontier
Deal found 5/30$247

Cheap Chicago to San Juan flights in May & June 2024

Find cheap flight options from Chicago to San Juan specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Prices were last updated on May 30, 2024.
The lowest fares we've come across on flights traveling from Chicago to San Juan in May and June 2024. For more flight deals, be sure to check back very soon.
Wed 6/128:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Mon 6/1712:30 pmSJU - ORD
1 stop20h 51mSpirit Airlines
Deal found 5/29$193
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sun 6/1611:08 pmSJU - ORD
1 stop11h 53mSpirit Airlines
Deal found 5/29$194
Wed 6/265:05 amORD - SJU
1 stop11h 25mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/30$195
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/30$195
Sat 6/85:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Tue 6/112:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/29$196
Wed 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 7/39:06 pmSJU - ORD
1 stop28h 49mSpirit Airlines
Deal found 5/29$197
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/25:40 amSJU - ORD
2 stops16h 07mSpirit Airlines
Deal found 5/29$198
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/30$199
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Fri 7/57:06 pmSJU - ORD
1 stop6h 49mSpirit Airlines
Deal found 5/28$200

Chicago to San Juan 2024 flight deals

Discover exclusive flight deals for travel between Chicago and San Juan in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Data last updated May 30, 2024.
The lowest fares we've come across on flights traveling from Chicago to San Juan in May and June 2024. For more flight deals, be sure to check back very soon.
Mon 9/169:25 pmORD - SJU
2 stops13h 03mSpirit Airlines
Sat 9/215:51 amSJU - ORD
2 stops13h 44mSpirit Airlines
Deal found 5/29$192
Wed 6/128:50 pmORD - SJU
1 stop22h 35mSpirit Airlines
Mon 6/1712:30 pmSJU - ORD
1 stop20h 51mSpirit Airlines
Deal found 5/29$193
Thu 9/511:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Mon 9/95:51 amSJU - ORD
1 stop27h 42mSpirit Airlines
Deal found 5/29$194
Wed 9/119:04 pmORD - SJU
1 stop28h 51mSpirit Airlines
Fri 9/205:51 amSJU - ORD
1 stop27h 42mSpirit Airlines
Deal found 5/29$195
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/30$195
Mon 7/110:27 amORD - SJU
1 stop7h 38mSpirit Airlines
Wed 7/1012:44 pmSJU - ORD
1 stop7h 05mSpirit Airlines
Deal found 5/29$196
Wed 6/2610:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 7/39:06 pmSJU - ORD
1 stop28h 49mSpirit Airlines
Deal found 5/29$197
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/25:40 amSJU - ORD
2 stops16h 07mSpirit Airlines
Deal found 5/29$198
Tue 6/258:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Tue 7/212:41 pmSJU - ORD
1 stop9h 29mSpirit Airlines
Deal found 5/30$199

Non-stop flights to San Juan from Chicago

Discover non-stop flight options from Chicago to San Juan. 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 2,784,634 searches. Data last updated May 30, 2024.
Take a look at some of the direct flights traveling from Chicago to San Juan in the near future. Search for alternative flights from Chicago to San Juan by utilizing the search form above.
Tue 6/259:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Tue 7/23:49 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 5/29$201
Tue 8/209:23 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sat 8/246:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$202
Wed 8/2111:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Sat 8/246:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/28$203
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Thu 7/46:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/29$204
Fri 8/2311:06 amORD - SJU
Nonstop4h 55mSpirit Airlines
Tue 8/276:00 amSJU - ORD
Nonstop5h 14mSpirit Airlines
Deal found 5/29$206
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sun 6/166:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/29$207
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Sun 6/166:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/29$209
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Tue 7/26:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/30$214
Tue 6/2510:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Fri 7/56:00 amSJU - ORD
Nonstop5h 09mSpirit Airlines
Deal found 5/28$216

Chicago to San Juan flights leaving soon

Find last-minute flight options from Chicago to San Juan 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 2,784,634 searches. Data last updated May 30, 2024.
Users seeking a last-minute flight from Chicago to San Juan should consider booking one of these fares. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Tue 6/1111:00 amSJU - MDW
2 stops11h 20mFrontier
Deal found 5/30$195
Sat 6/85:11 pmORD - SJU
Nonstop4h 47mSpirit Airlines
Tue 6/112:59 pmSJU - ORD
1 stop18h 22mSpirit Airlines
Deal found 5/29$196
Thu 6/65:34 pmORD - SJU
1 stop7h 59mSpirit Airlines
Wed 6/122:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 5/30$201
Fri 6/78:27 amMDW - SJU
1 stop17h 41mFrontier
Wed 6/1210:15 pmSJU - MDW
2 stops22h 41mFrontier
Deal found 5/30$201
Fri 6/710:59 amORD - SJU
Nonstop4h 49mSpirit Airlines
Wed 6/129:06 pmSJU - ORD
1 stop13h 55mSpirit Airlines
Deal found 5/29$204
Sat 6/83:56 pmORD - SJU
1 stop27h 29mSpirit Airlines
Wed 6/122:00 pmSJU - ORD
1 stop20h 04mSpirit Airlines
Deal found 5/29$206
Wed 6/58:50 pmORD - SJU
3 stops28h 43mSpirit Airlines
Wed 6/122:00 pmSJU - ORD
1 stop27h 44mSpirit Airlines
Deal found 5/29$208
Sat 6/89:41 pmORD - SJU
1 stop21h 44mSpirit Airlines
Fri 6/1412:10 pmSJU - ORD
1 stop12h 11mSpirit Airlines
Deal found 5/29$209
Fri 6/75:58 pmORD - SJU
1 stop15h 45mFrontier
Tue 6/113:08 amSJU - ORD
1 stop23h 00mFrontier
Deal found 5/30$213

One-way flights to San Juan from Chicago

Search for one-way flight options from Chicago to San Juan. 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 2,784,634 searches. Data last updated May 30, 2024.
Users in need of a one-way flight from Chicago to San Juan can choose from these deals. Those needing a return flight from Chicago to San Juan can use the search form above.
Tue 8/275:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Deal found 5/28$46
Mon 8/266:32 pmORD - SJU
1 stop15h 56mSpirit Airlines
Deal found 5/28$56
Tue 6/118:50 pmORD - SJU
1 stop15h 12mSpirit Airlines
Deal found 5/28$57
Tue 6/118:50 pmORD - SJU
1 stop21h 15mSpirit Airlines
Deal found 5/30$62
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Deal found 5/29$63
Tue 8/275:00 amORD - SJU
2 stops18h 02mSpirit Airlines
Deal found 5/28$65
Tue 8/207:27 amORD - SJU
1 stop10h 30mSpirit Airlines
Deal found 5/30$69
Tue 6/119:11 amORD - SJU
Nonstop4h 48mSpirit Airlines
Deal found 5/29$70
Wed 8/215:00 amORD - SJU
1 stop13h 11mSpirit Airlines
Deal found 5/29$73

Find flights from Chicago to San Juan within your budget

Customize your flight search to find flights from Chicago to San Juan 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 2,784,634 searches. Data last updated May 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$113 - $369

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop13h 11m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$113

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$116

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/20

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Tue 8/27

1 stop10h 28m

$120

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 9/10

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 9/24

1 stop29h 03m

$121

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/27

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 8/27

2 stops17h 27m

$122

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/27

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Wed 8/28

Nonstop5h 14m

$123

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/27

1 stop13h 11m

San Juan Luis Munoz Marin Intl

Sat 8/31

1 stop11h 50m

$191

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 6/8

1 stop16h 37m

San Juan Luis Munoz Marin Intl

Wed 6/12

1 stop9h 24m

$195

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 8/8

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Wed 8/14

1 stop8h 16m

$369

Flights are sorted by cheapest first

Deals found on 5/30

How far ahead should I book a flight from Chicago to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Juan. Price data was last updated on May 24, 2024.
To ensure you get the cheapest price possible for a flight from Chicago to San Juan, you should look to book at least 56 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Search Deals

What is the cheapest day to fly from Chicago to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Juan. Price data was last updated on May 26, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to San Juan flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Best time to book a flight from Chicago to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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.

Temperature and rainfall in San Juan by month

Plan your trip to San Juan by taking into account the average temperature and rainfall totals by month.

SJU

Temperature

77 - 82.4 °F

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated May 30, 2024.
To help decide which airline to fly from Chicago to San Juan, see what other customers have to say about Spirit Airlines, Frontier and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,457 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,457 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

United Airlines
7.4
Good
10,777 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

American Airlines
7.3
Good
14,284 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Spirit Airlines
6.4
Okay
8,616 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,016 reviews
Delta
8.0
Very good
10,457 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

8.0

Food

7.4

Comfort

7.9

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Juan. 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 San Juan for under $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to San Juan for under $200. The cheapest flight booked recently is on Spirit Airlines for just $113, but on average you can expect to pay $128.

  • Are there nonstop flights from Chicago to San Juan for under $300 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to San Juan under $300. A good price for a nonstop flight from Chicago to San Juan is less than $218.

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

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

  • What is the cheapest airline to fly from Chicago to San Juan round-trip?

    Cheapflights users have booked flights from Chicago to San Juan round-trip from $113. Spirit Airlines is priced at 64% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago to San Juan?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to San Juan on time: Alaska Airlines (93%), American Airlines (92%), United Airlines (83%).

  • What are the cheapest flights from Chicago to San Juan?

    Looking at all options, your cheapest flight can be booked for $105. While the most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl) can be booked for $115 on average our data indicates $600 when flying from Chicago to San Juan.

  • What does ORD to SJU mean?

    ORD stands for Chicago O'Hare Intl Airport, while SJU stands for San Juan Luis Munoz Marin Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Ponce Mercedita Airport (PSE), San Juan Isla Grande Airport (SIG), Culebra Airport (CPX), Vieques Airport (VQS), Ceiba J. Aponte de la Torre Airport (NRR).

  • Where are the most common layover locations when flying from Chicago to San Juan?

    Chicago to San Juan flights have a layover in Orlando most of the time. Charlotte follows Orlando in terms of the most common layover location on Chicago to San Juan flights.

  • What are some popular things to do or see while on a layover in Orlando?

    Walt Disney World Resort, Universal Orlando Resort, and International Drive are the most popular attractions in Orlando if you're in need of something to do during your layover. Walt Disney World Resort, Universal Orlando Resort, and International Drive are located about 16.2 mi, 10.3 mi, and 9.9 mi, respectively from Orlando. Those landing in Orlando looking to spend some time exploring during their layover can rent a car for about $33 per day.

  • What are some popular points of interest to see during a layover in Charlotte?

    Carowind, North Carolina Blumenthal Performing Arts Center, and NASCAR Hall of Fame are the most popular attractions in Charlotte if you're in need of something to do during your layover. Carowind, North Carolina Blumenthal Performing Arts Center, and NASCAR Hall of Fame can be visited by traveling about 8.2 mi, 5.8 mi, and 5.7 mi respectively from Charlotte Douglas. Travelers can rent a car at Charlotte Douglas for an average daily rate of $54 to make sightseeing during their layover a little easier.

  • Where are the least popular layover locations for Chicago to San Juan flights?

    Of the flights from Chicago to San Juan that have layovers, the fewest flights stop in Atlanta.

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

    The amount of baggage you can bring on your Chicago to San Juan 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 San Juan with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to San Juan 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 San Juan that include hotel bookings?

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

  • How can I find direct flights from Chicago to San Juan?

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

  • Can I find deals for business class flights from Chicago to San Juan?

    Yes. Cheapflights offers flight deals from Chicago to San Juan 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 San Juan that allow pets onboard?

    Many airlines flying from Chicago to San Juan 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 San Juan?

    Yes, you can often find last-minute deals on Chicago to San Juan 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 San Juan flight deals updated?

    The Chicago to San Juan flight deals you see on this page were last updated on 5/30.

  • What are the most popular airlines that fly from Chicago to San Juan?

    Consider American Airlines, Alaska Airlines or JetBlue when booking your flight. These represent the most popular airlines when flying from Chicago to San Juan.

  • What is the cheapest month to book a flight from Chicago to San Juan?

    Currently, September is the cheapest month in which you can book a flight from Chicago to San Juan (average of $247). Flying from Chicago to San Juan in March is currently the most expensive (average of $338). 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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See prices for flight routes from nearby airports that may be better suited for you.

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Top 7 airlines flying from Chicago to San Juan

Discover the top 7 airlines that operate flights from Chicago to San Juan. 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 2,784,634 searches. Data last updated May 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$261FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$130Average$316FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$135Average$555FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$152Average$498FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
JetBlueCheapest$172Average$405FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
Alaska AirlinesCheapest$301Average$479FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
American AirlinesCheapest$301Average$485FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
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Search flights from Chicago to San Juan by cabin class

Find flights from Chicago to San Juan, 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 San Juan

Find hourly flight availability from Chicago to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 30, 2024.
1%of flight departuresEarly morningMidnight to 6 am
93%of flight departuresMorning6 am to noon
6%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to San Juan

Explore weekly flight availability from Chicago to San Juan. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 30, 2024.
Sunday5daily flights
Monday7daily flights
Tuesday7daily flights
Wednesday7daily flights
Thursday7daily flights
Friday7daily flights
Saturday10daily flights

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Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago to San Juan flexibly with Cheapflights today.

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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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