How many flights from Chicago to San Juan are non-stop?

In the trailing 90 days, approximately 32.2% of flights from Chicago to San Juan were non-stop. This indicates that a significant portion of travelers will likely have connecting flights. For those routes involving stopovers, the median number of stopovers observed was 2. Travelers prioritizing direct routes should consider this percentage when planning their journey.

What's the flight time from Chicago to San Juan?

The typical direct flight from Chicago to San Juan has a duration of 4 hours and 56 minutes. For flights with one stop, the median travel time increases to 7 hours and 55 minutes. This route covers an approximate distance of 3338 kilometers. Travelers should account for these differences in duration based on their flight choice.

How often do cheap flights from Chicago to San Juan come up?

Historically, cheap flights from Chicago to San Juan are classified as frequent. This suggests that travelers have regular opportunities to find good deals on this route. The consistent availability of competitive fares makes it a favorable route for those seeking value. This frequency has been observed across the trailing 30 days.

Flights From Chicago

To San Juan

Cheap Flights from Chicago to San Juan

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Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to San Juan

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to San Juan

Explore current cheapest deals departing from Chicago to San Juan

2026-08-17 – 2026-08-27
CHI - San Juan
74% AI deal score
$200
$165
Round trip
2026-09-01 – 2026-09-05
CHI - San Juan
79% AI deal score
$217
$165
Round trip
2026-08-25 – 2026-08-29
CHI - San Juan
73% AI deal score
$226
$186
Round trip
2026-08-23 – 2026-08-29
CHI - San Juan
72% AI deal score
$213
$186
Round trip
2026-09-01 – 2026-09-06
CHI - San Juan
71% AI deal score
$212
$188
Round trip
2026-08-22 – 2026-08-27
CHI - San Juan
72% AI deal score
$220
$191
Round trip
2026-08-19 – 2026-08-22
CHI - San Juan
73% AI deal score
$232
$193
Round trip
2026-08-23 – 2026-08-28
CHI - San Juan
71% AI deal score
$220
$195
Round trip
2026-08-17 – 2026-08-25
CHI - San Juan
70% AI deal score
$209
$195
Round trip
2026-08-17 – 2026-08-30
CHI - San Juan
67% AI deal score
$193
$196
Round trip

Chicago to San Juan: Overview

Insights for flights from Chicago to San Juan

For cheap flights from Chicago to San Juan, fares typically range from $210–$601, with a median of $418 over a 90-day period. Right now, current fares are above the typical level for this route. Only 7% of recent fares were classified as a good price, indicating that finding a low fare may require some flexibility.

The journey from Chicago to San Juan is classified as a medium-haul flight, covering a distance of 3338 kilometers. This distance means you should expect a significant travel duration, often involving connections to reach your destination.

When considering how long is the flight from Chicago to San Juan, a typical journey, including connections, takes approximately 12h 46m. This duration reflects that most itineraries on this route involve at least one stopover, extending the total travel time.

Most itineraries for this route are connecting flights, with only 32.2% of recent fares being non-stop. For those itineraries that do connect, the median number of stopovers is 2, which contributes to the longer overall travel times.

If you are looking for the cheapest time to fly from Chicago to San Juan, September stands out with a median fare of $168. Other cost-effective months include April, with a median fare of $194, and July, where the median fare is $210. New deals for this route appear almost daily, so setting up a price alert can help you secure a favorable fare during these cheaper periods.

How much is a round trip from Chicago to San Juan

Regular price: $187 - $349

Prices are currently below the regular range.

Regular prices for flights from Chicago to San Juan typically range from $187 to $349. The current lowest deal is $172 with Frontier Airlines for travel from Aug 25-Aug 30.

now $172

Low $187

High $349

The cheapest time to fly from Chicago to San Juan

Flights from Chicago to San Juan are cheapest in September, with a median price of $168. The most expensive month to fly is February, with a median price of $1006. Prices are generally lower from April to December.

September

Cheapest

Flights from $168

February

Most Expensive

Flights from $1,006

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to San Juan

Frontier Airlines

Last-minute flights going from Chicago to San Juan

Mon, Jul 27

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$383

$265

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$386

$246

One-way

Tue, Jul 28

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$386

$259

One-way

Wed, Jul 29

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$279

$214

One-way

Wed, Jul 29

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$386

$270

One-way

Sat, Aug 1

⌛ Last-Minute

MDW - San Juan

Chicago (MDW) - San Juan (SJU)

Southwest Airlines

$471

$396

One-way

Biggest price drops on these dates for flights from Chicago to San Juan

2 nights

Jul 28 - Jul 30

$386 → $246

36%

1 night

Jul 28 - Jul 29

$386 → $259

33%

7 nights

Dec 8 - Dec 15

$459 → $335

27%

3 nights

Jul 27 - Jul 30

$383 → $265

31%

Popular Airports to fly from Chicago to San Juan

Chicago - San Juan route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from Chicago to San Juan are above the typical level at $418.

📅 Best time to fly

Fly in September for the best prices

Historically, September is the cheapest month to fly, with a median price of $168.

⏱️ Flight duration

Flights typically take 12h 46m

The median flight duration from Chicago to San Juan is 12 hours and 46 minutes.

✈️ Airlines & availability

Frontier Airlines offers direct flights

Frontier Airlines provides direct flights on this route, with other connecting options also available.

🏆 Airline highlight

Frontier Airlines has a deal for $172

Frontier Airlines offers a deal for $172 from August 25 to August 30.

🎯 Booking tip

Deals are frequent on this route

Deals on flights from Chicago to San Juan are frequent, appearing often over 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers flights to San Juan from Chicago, with prices starting from $137.

📍 ~23 km from Chicago (reachable by car or train).

💸 Flights from ~$137

Chicago Midway International (MDW)

Chicago Midway International Airport is an alternative for flights to San Juan from Chicago.

📍 ~15 km from Chicago (reachable by car or train).

💸 Flights from ~$236

Chicago Rockford International (RFD)

Chicago Rockford International Airport is another option for flights to San Juan from Chicago.

📍 ~110 km from Chicago (reachable by car).

💸 Flights from ~$276

San Juan main airports to arrive at

Luis Muñoz Marín International (SJU)

Cheapest

Luis Muñoz Marín International Airport is a good option for flights from Chicago to San Juan.

📍 ~10 km from San Juan (reachable by car)

💸 Flights from ~$137

Airports nearby San Juan used as alternative

Aguadilla Rafael Hernandez (BQN)

Cheapest

Aguadilla Rafael Hernandez is a primary alternative for flights to the US mainland from Puerto Rico.

📍 ~135 km from San Juan (reachable by car)

💸 Flights from ~$283

Business & First Class Flight Deals to San Juan

89% AI deal score

$1,376

$912

Save $464

Frequently Asked Questions About Flights to San Juan

Historically, the optimal booking window for flights from Chicago to San Juan is typically between 28 and 59 days prior to departure. During this period, the average price observed was around $332. Prices tend to be higher for last-minute bookings, with flights purchased 0-6 days out averaging $533. Conversely, booking more than 60 days in advance also shows a higher average price of $453, suggesting that waiting for the sweet spot can lead to savings.

Across the trailing quarter, a good price for a flight from Chicago to San Juan is considered to be $210 or less. The median price for this route historically stands at $418. Fares can go significantly higher, with prices at the 75th percentile reaching $601. Travelers aiming for a budget-friendly trip should target fares around the $210 mark.

Historically, September has been the cheapest month to fly from Chicago to San Juan, with a median price of $168. April also offers competitive fares, showing a median price of $194. July, while also listed among the cheaper months with a median of $210, was also the most expensive month overall, indicating price variability. The annual median price for this route is $418.

Related routes

More routes from Chicago

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Flights to San Juan from other cities

Flights from Copenhagen to San Juan Flights from Dallas to San Juan Flights from Dubai to San Juan Flights from Edinburgh to San Juan Flights from Fort Lauderdale to San Juan Flights from Hong Kong to San Juan Flights from Houston to San Juan Flights from La Paz to San Juan Flights from Mendoza to San Juan Flights from New York to San Juan Flights from Orlando to San Juan Flights from Philadelphia to San Juan

Chicago to San Juan: Overview

Insights for flights from Chicago to San Juan

How much is a round trip from Chicago to San Juan

Regular price: $187 - $349

Prices are currently below the regular range.

Regular prices for flights from Chicago to San Juan typically range from $187 to $349. The current lowest deal is $172 with Frontier Airlines for travel from Aug 25-Aug 30.

now $172

Low $187

High $349

The cheapest time to fly from Chicago to San Juan

September

Cheapest

Flights from $168

February

Most Expensive

Flights from $1,006

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec