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

Across the trailing 90 days, approximately 32.2% of flights from Chicago to San Juan were non-stop. For flights that included stopovers, travelers typically experienced 2 connections. This indicates that while direct options are available, a significant portion of routes involve at least one stop.

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

The typical direct flight from Chicago to San Juan has a median duration of 4 hours and 56 minutes. For flights with one stop, the median travel time extends to 7 hours and 55 minutes. The total air distance covered on this route is approximately 3338 kilometers.

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

Based on historical trends over the trailing 30 days, cheap flights from Chicago to San Juan come up frequently. This indicates a consistent availability of more affordable fares for this particular route. Travelers can often find competitive prices when planning their trips.

Flights From Chicago

To San Juan

Cheap Flights from Chicago to San Juan

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

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

Prices updated 1 day ago

459 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 8, 2026.)

Today’s best flight deals from Chicago to San Juan

Explore current cheapest deals departing from Chicago to San Juan

2026-11-15 – 2026-11-23
CHI - San Juan
87% AI deal score
$310
$183
Round trip
2026-10-04 – 2026-10-21
CHI - San Juan
84% AI deal score
$284
$196
Round trip
2026-09-07 – 2026-09-22
CHI - San Juan
85% AI deal score
$302
$197
Round trip
2026-09-07 – 2026-09-23
CHI - San Juan
83% AI deal score
$300
$197
Round trip
2026-09-06 – 2026-09-23
CHI - San Juan
84% AI deal score
$321
$203
Round trip
2026-10-04 – 2026-10-14
CHI - San Juan
84% AI deal score
$303
$205
Round trip
2026-09-06 – 2026-09-22
CHI - San Juan
85% AI deal score
$324
$207
Round trip
2026-11-08 – 2026-11-12
CHI - San Juan
87% AI deal score
$329
$208
Round trip
2026-09-22 – 2026-09-30
CHI - San Juan
76% AI deal score
$258
$209
Round trip
2026-10-04 – 2026-10-07
CHI - San Juan
86% AI deal score
$341
$209
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 deals may require some flexibility.

When is the cheapest time to fly from Chicago to San Juan? The data indicates that September is typically the most affordable month, with a median fare of $168. Other cost-effective options include April, with a median fare of $194, and July, where the median fare is $210. Planning your trip around these months could result in lower prices.

A typical journey from Chicago to San Juan takes approximately 12h 46m, including connections. This is a medium-haul route, covering a distance of 3338 kilometers. Most itineraries connect at least once, with only 32.2% of recent fares being direct flights from Chicago to San Juan. For connecting itineraries, the median number of stopovers is 2.

How much is a round trip from Chicago to San Juan

Regular price: $274 - $742

Prices are currently below the regular range.

The regular price range for flights from Chicago to San Juan is $274 to $742. The current lowest deal is $196 with JetBlue Airways for travel from Dec 8-Dec 17.

now $196

Low $274

High $742

The cheapest time to fly from Chicago to San Juan

The cheapest month to fly from Chicago to San Juan is September, with a median price of $168. The most expensive month 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

American Airlines

Last-minute flights going from Chicago to San Juan

Sun, Sep 6

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$317

$180

One-way

Sun, Sep 6

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$381

$263

One-way

Mon, Sep 7

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

Frontier Airlines

$331

$261

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

United Airlines

$195

$363

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

United Airlines

$196

$363

One-way

Tue, Sep 15

⌛ Last-Minute

ORD - San Juan

Chicago (ORD) - San Juan (SJU)

United Airlines

$208

$378

One-way

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

2 nights

Sep 2 - Sep 4

$523 → $279

47%

4 nights

Sep 5 - Sep 9

$462 → $235

49%

1 night

Sep 4 - Sep 5

$473 → $250

47%

2 nights

Sep 3 - Sep 5

$472 → $251

47%

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 for this route.

📅 Best time to fly

September, April, and July offer the lowest median prices.

Historically, September ($168), April ($194), and July ($210) have offered the lowest median prices.

⏱️ Flight duration

Flights typically take 12h 46m.

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

✈️ Airlines & availability

Connecting flights are dominant on this route.

Only 32.2% of flights are direct, with connecting routes typically having 2 stopovers.

🏆 Airline highlight

American Airlines offers direct flights.

American Airlines is an available carrier for direct flights on this route.

🎯 Booking tip

Deals are frequent for this route.

Deals for flights from Chicago to San Juan are frequently available within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Chicago O Hare International Airport offers the cheapest flights to San Juan from Chicago.

📍 ~25 km from Chicago city center (reachable by car or train).

💸 Flights from ~$128

San Juan main airports to arrive at

Luis Muñoz Marín International (SJU)

Cheapest

Luis Muñoz Marín International Airport is a key arrival airport for flights from Chicago to San Juan.

📍 ~11 km from San Juan (reachable by car)

💸 Flights from ~$128

Airports nearby San Juan used as alternative

Aguadilla Rafael Hernandez (BQN)

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

📍 ~150 km from San Juan (reachable by car, approximately a 2-hour drive)

💸 Flights from ~$326

Business & First Class Flight Deals to San Juan

$722

Save $841

United Airlines

Business Class

Frequently Asked Questions About Flights to San Juan

Historically, the best time to purchase tickets for flights from Chicago to San Juan is typically 28-59 days before departure. During this window, the average price observed was $332. Prices tend to be higher for last-minute bookings, with flights purchased 0-6 days out averaging around $533. For those planning further ahead, tickets bought 60+ days in advance had an average price of $453.

A good price for a flight from Chicago to San Juan is considered to be around $210 or less. This threshold represents the lowest 25% of prices observed across the trailing quarter. The median price for this route over the same period was $418, while prices in the higher range could go up to $601.

Historically, the cheapest months to fly from Chicago to San Juan are September, April, and July. In September, the median price was $168, followed by April at $194, and July at $210. These prices are notably lower than the annual median price of $418 for this route, based on data from the trailing 270 days.

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: $274 - $742

Prices are currently below the regular range.

The regular price range for flights from Chicago to San Juan is $274 to $742. The current lowest deal is $196 with JetBlue Airways for travel from Dec 8-Dec 17.

now $196

Low $274

High $742

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